Skip to main content
Log in

7-Aminocoumarins (Review)

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The principal methods for the synthesis of 7-amino coumarins and their reactivities are described. The luminescence properties and generation characteristics of this important class of organic dyes are examined.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

Literature cited

  1. S. Wawzonek, in: Heterocyclic Compounds, R. Elderfield, ed., Vol. 2, Wiley (1951).

  2. T. Kosuge and D. Gilchrist, in: Mycotoxic Fungi, Mycotoxins, and Mycotoxicoses, T. D. Myllie, ed., Vol. 1, Marcel Dekker, New York (1977), p. 239; Chem. Abstr.,88, 58950 (1978).

    Google Scholar 

  3. W. L. Stanley, in: Aspects of Plant Phenolic Chemistry, Proc. Symp., 3rd Univ. Toronto, 1963 (publ. 1964), p. 79; Chem. Abstr.,61, 4304 (1964).

  4. T. S. Soine, J. Pharm. Sci., 53, No. 3, 231 (1964).

    Google Scholar 

  5. R. D. H. Murray, Arom. Heteroarom. Chem.,5, 472 (1977).

    Google Scholar 

  6. V. K. Ahluwalia, K. Rani, and M. Sunita, J. Chem. Sci.,3, 1 (1977); Chem. Abstr.,89, 24056 (1978).

    Google Scholar 

  7. T. J. Mabry and A. Ulubelen, J. Agric. Food Chem.,28, 188 (1980).

    Google Scholar 

  8. H. Held, Med. Monatschr. Pharm.,3, 33 (1980); Chem. Abstr.,92, 157415 (1980).

    Google Scholar 

  9. J. Royer, Quantum Theory Chem. React.,2, 169 (1981).

    Google Scholar 

  10. J. Staunton, in: Comprehensive Organic Chemistry, P. G. Sammes, ed., Vol. 4, Pergamon Press, Oxford (1979), p. 629.

    Google Scholar 

  11. P. Ilić, B. Mohar, J. V. Knop, A. Jurić, and N. Trinajstić, J. Heterocycl. Chem.,19, 625 (1982).

    Google Scholar 

  12. X.-Q. Zhang, L. Ye, Hsu Chung Ts'ao Yao,11, 566 (1980); Chem. Abstr.,94, 180729 (1981).

    Google Scholar 

  13. A. G. Gonzalez, J. T. Barroso, Z. D. Yorge, and F. R. Luis, Rev. R. Acad. Cienc. Exactas, Fiz. Nat. Madrid,75, 811 (1981).

    Google Scholar 

  14. H. Duddeck and M. Kasier, Org. Magn. Reson.,20, 55 (1982).

    Google Scholar 

  15. S. C. Haydon, Spectrosc. Lett.,8, 815 (1975).

    Google Scholar 

  16. D. Liebermann, A. Desnoes, and L. Hengl, Compt. Rend.,232, 2027 (1951).

    Google Scholar 

  17. E. Kobayashi and K. Suzuki, Japanese Patent No. 18632; Chem. Abstr.,65, 7329 (1966).

    Google Scholar 

  18. L. A. Holt, I. H. Leaver, and B. Milligan, Text. Res. J.,46, 539 (1976).

    Google Scholar 

  19. S. D. Mehendale and S. V. Sunthankar, Ind. J. Chem.,8, 969 (1970).

    Google Scholar 

  20. A. Clayton, J. Chem. Soc.,97, 1350 (1910).

    Google Scholar 

  21. C. Antonello, F. Carlasare, P. Malfer, and P. Siliprandi, Farmaco Ed. Sci.,29, 697 (1974); Chem. Abstr.,81, 151916 (1974).

    Google Scholar 

  22. R. H. Mehta and S. Sethna, J. Ind. Chem. Soc.,41, 122 (1964).

    Google Scholar 

  23. M. Julia and G. Tchernoff, Bull. Soc. Chim. Fr., Nos. 7–8, 779 (1952).

    Google Scholar 

  24. M. Julia, French Patent No. 1052747; Chem. Abstr.,54, 579 (1960).

    Google Scholar 

  25. K. Okumura and K. Kondo, Japanese Patent No. 4669; Chem. Abstr.,67, 90674 (1967).

    Google Scholar 

  26. M. Ichikawa and H. Ichibagase, Chem. Pharm. Bull.,16, 2093 (1968).

    Google Scholar 

  27. T. Yanagisawa and O. Kotoyori, US Patent No. 3514471; Chem. Abstr.,73, 35221 (1970).

    Google Scholar 

  28. C. W. Schellhammer, K. W. Mueller, and R. Raue, Belgain Patent No. 660602; Chem. Abstr.,63, 18036 (1965).

    Google Scholar 

  29. C. W. Schellhammer, K. W. Mueller, and R. Raue, US Patent No. 3352885; Chem. Abstr.,69, 3715 (1968).

    Google Scholar 

  30. C. W. Schellhammer, A. Dorlars, and W. D. Wirth, British Patent No. 1163876; Chem. Abstr.72, 22599 (1970).

    Google Scholar 

  31. A. Dorlars and H. Gold, West German Patent No. 2037854; Chem. Abstr.,77, 7314 (1972).

    Google Scholar 

  32. A. Dorlars, C. W. Schellhammer, and W. D. Wirth, US Patent No. 4005098; Chem. Abstr.,86, 122955 (1977).

    Google Scholar 

  33. P. Czerney and H. Hartmann, J. Prakt. Chem.,324, 21 (1982).

    Google Scholar 

  34. H. Hausermann, US Patent No. 2929822; Chem. Abstr.,55, 4538b (1961).

    Google Scholar 

  35. H. Hausermann, US Patent No. 2881186; Chem. Abstr.,56, 10105 (1962).

    Google Scholar 

  36. Farbenfabriken Bayer A.-G., French Patent No. 2016308; Chem. Abstr.,74, 127560 (1971).

    Google Scholar 

  37. H. Knupfer and C. W. Schellhammer, US Patent No. 3681397; Cl. 260-343.2R, C07d7/24.

  38. J. R. Geigy A.-G., British Patent No. 786234; Chem. Abstr.,52, 7725b (1958).

    Google Scholar 

  39. Showa Chemical Industries, Ltd., British Patent No. 1200699; Chem. Abstr.,73, 87664 (1970).

    Google Scholar 

  40. Showa Chemical Industries, Ltd., British Patent No. 1200698; Chem. Abstr.,73, 121567 (1970).

    Google Scholar 

  41. T. Yanagisawa and O. Kotoyori, Japanese Patent No. 27149; Chem. Abstr.,73, 109687 (1970)

    Google Scholar 

  42. H. Schlaepfer, West German Patent No. 2712496; Chem. Abstr.,88, 38962 (1978).

    Google Scholar 

  43. R. Raue and H. Gold, Belgian Patent No. 621482; Chem. Abstr.,59, 15420 (1963).

    Google Scholar 

  44. H. Schlaepfer, West German Patent No.2329991; Chem. Abstr.,81, 51143 (1974).

    Google Scholar 

  45. H. Hamisch, West German Patent No. 2065076; Chem. Abstr.,77, 128075 (1972).

    Google Scholar 

  46. H. Hauesermann and J. Voltz, West German Patent No. 1098125; Chem. Abstr.,56, 10158f, 10159 (1962).

    Google Scholar 

  47. K. Sato, Japanese Patent No. 80122; Chem. Abstr.,80, 84703 (1974).

    Google Scholar 

  48. H. Harnisch, West German Patent No. 2065552; Chem. Abstr.,82, 87700 (1975).

    Google Scholar 

  49. H. Harnisch, West German Patent No. 2030507; Chem. Abstr.,76, 128826 (1972).

    Google Scholar 

  50. H. Harnisch, West German Patent No. 2058877; Chem. Abstr.,77, 128073 (1972).

    Google Scholar 

  51. M. Ohkawa and I. Takatsuki, West German Patent No. 2364478; Chem. Abstr.,82, 32460 (1975)

    Google Scholar 

  52. H. Sensui, S. Maeda, and T. Kurahashi, Japanese Patent No. 145735; Chem. Abstr.,92, 130611 (1980).

    Google Scholar 

  53. J. Dehnert and G. Grau, West German Patent No. 2011500; Chem. Abstr.,76, 60950 (1972).

    Google Scholar 

  54. P. Loew, West German Patent No. 2710285; Chem. Abstr.,87, 186083 (1977).

    Google Scholar 

  55. S. Koller, R. Zink, D. Reichel, and Y. Voltz, West German Patent No. 2142411; Chem. Abstr.,77, 36393 (1972).

    Google Scholar 

  56. J. Schroeder, H. Knupfer, and S. Petersen, West German Patent No. 2044991; Chem. Abstr.,77, 36394 (1972).

    Google Scholar 

  57. J. D. Kendall, H. R. J. Waddington, and G. F. Duffin, British Patent No. 867592; Chem. Abstr.,55, 21927 (1961).

    Google Scholar 

  58. S. Enomoto, K. Sato, and G. Suzuki, West German Patent No. 2005933; Chem. Abstr.,74, 65585 (1971).

    Google Scholar 

  59. W. Koch, Swiss Patent No. 580610; Chem. Abstr.,86, 29892 (1977).

    Google Scholar 

  60. W. Koch, West German Patent No. 2334168; Chem. Abstr.,81, 14720 (1974).

    Google Scholar 

  61. H. Sheuermann and D. Augart, West German Patent No. 2410634; Chem. Abstr.,83, 181110 (1975).

    Google Scholar 

  62. M. Patsch and C. Vamvakaris, West German Patent No. 2529434; Chem. Abstr.,86, 122953 (1977).

    Google Scholar 

  63. M. Patsch and C. Vamvakaris, West German Patent No. 2553294; Chem. Abstr.,87, 103365 (1977).

    Google Scholar 

  64. E. Kobayashi, Japanese Patent No. 00975; Chem. Abstr.,81, 93091 (1974).

    Google Scholar 

  65. J. R. Geigy, A.-G., French Patent No. 1320597; Chem. Abstr.,60, 3142 (1964).

    Google Scholar 

  66. T. Yanagisawa, Japanese Patent No. 37324; Chem. Abstr.,81, 51153 (1974).

    Google Scholar 

  67. T. Suzuki, Japanese Patent No. 37970; Chem. Abstr.,81, No. 12, 65247 (1974).

    Google Scholar 

  68. T. Sakaue and M. Uchiba, Kogyo Kagaku Zasshi,72, No. 6, 1339 (1969); Chem. Abstr.,72, No. 18, 9145 (1970).

    Google Scholar 

  69. H. Berneth and R. Raue, European Patent No. 56577; Chem. Abstr.,97, No. 24, 199547 (1982).

    Google Scholar 

  70. J. Schroder, West German Patent No. 2335218; Chem. Abstr.,82, No. 26, 172618 (1975).

    Google Scholar 

  71. K. Suzüki and T. Yanagisawa, Japanese Patent No. 37969; Chem. Abstr.,81, No. 16, 93087 (1974).

    Google Scholar 

  72. D. P. Specht, P. A. Martic, and S. Farid, Tetrahedron,38, No. 9, 1203 (1982).

    Google Scholar 

  73. N. V. Subba Rao and V. Sundaramurthy, Proc. Indian Acad. Sci.,42A, 249 (1955).

    Google Scholar 

  74. B. Sreenivasulu, V. S. Murthy, and N. V. Subba Rao, Curr. Sci.,38, No. 10, 240 (1969).

    Google Scholar 

  75. Y. Ishii, J. Agric. Chem. Soc Jpn.,27, 310 (1953); Chem. Abstr.,49, No. 8, 5464 (1955).

    Google Scholar 

  76. Y. Sumiki and Y. Ishii, Japanese Patent No. 6134; Chem. Abstr.,50, No. 11, 7874 (1956).

    Google Scholar 

  77. K. S. R. Krishna Mohan Rao and N. V. Subba Rao, in: Symp. Syn Heterocycl. Compounds Physiol. Interest, Hyderabad, India, 1964 (pub. 1966), p. 129; Chem. Abstr.,69, No. 9, 36002 (1968).

  78. Y. Sumuki and Y. Ishii, Japanese Patent No. 6915; Chem. Abstr.,67, No. 9, 43681 (1967).

    Google Scholar 

  79. K. S. R. Krishna Mohan Rao and N. V. Subba Rao, Proc. Ind. Acad. Sci., Sect. A,67, No. 1, 42 (1968).

    Google Scholar 

  80. M. Darbarwar, V. Sundaramurthy, and N. V. Subba Rao, Ind. J. Chem.,11, No. 2, 115 (1973).

    Google Scholar 

  81. B. Sreenivasulu, V. Sundaramurthy, and N. V. Subba Rao, Proc. Ind. Acad. Sci., Sect. A, No. 6, 273 (1974).

    Google Scholar 

  82. H. Von Pechmann, Chem. Ber.,32, 3681 (1899).

    Google Scholar 

  83. H. Von Pechmann and O. Schwarz, Chem. Ber.,32, 3696 (1899).

    Google Scholar 

  84. H. Von Pechmann and O. Schwarz, Chem. Ber.,32, 3699 (1899).

    Google Scholar 

  85. L. L. Woods and M. M. Fooladi, J. Chem. Eng. Data,13, No. 3, 440 (1968).

    Google Scholar 

  86. R. L. Atkins and D. E. Bliss, J. Org. Chem.,43, No. 10, 1975 (1978).

    Google Scholar 

  87. Ya. Prikl and C. Fisar, Czechoslovak Patent No. 180246; Chem. Abstr.,93, No. 3, 26279 (1980).

    Google Scholar 

  88. Y. Haeberly, US Patent No. 3356689; Chem. Abstr.,68, No. 23, 104984 (1968).

    Google Scholar 

  89. E. R. Bissel, A. R. Mitchell, and R. E. Smith, J. Org. Chem.,45, No. 12, 2283 (1980).

    Google Scholar 

  90. N. V. Subba Rao and V. Sundaramurthy, Proc. Indian Acad. Sci.,43A, 149 (1956).

    Google Scholar 

  91. J. E. Pretka, US Patent No. 3008969; Chem. Abstr.,57, No. 10, 12440 (1962).

    Google Scholar 

  92. J. D. Kendall, H. R. J. Waddington, and G. E. Duffin, British Patent No. 856068; Chem. Abstr.,55, No. 11, 10164 (1961).

    Google Scholar 

  93. J. Haeberli and R. I. Warwick, US Patent No. 3322794; Cl. 260-343.2.

  94. J. R. Geigy A.-G., Netherlands Patent Application No. 6511305; Chem. Abstr.,65, No. 5, 7329 (1966).

    Google Scholar 

  95. H. Umemoto, T. Kitao, and K. Konishi, Kogyo Kagaku Zasshi,73, No. 6, 1146 (1970); Chem. Abstr.,73, No. 26, 131949 (1970).

    Google Scholar 

  96. H. Majerowa, Czechoslovakian Patent No. 143698; Chem. Abstr.,78, No. 4, 17641 (1973).

    Google Scholar 

  97. L. L. Woods and S. M. Shamma, J. Chem. Eng. Data,16, No. 1, 101 (1971).

    Google Scholar 

  98. F. Lauria, V. Vecchietti, R. Tommasini, and N. Passerini, West German Patent No. 2459076; Chem. Abstr.,83, No. 19, 163996 (1975).

    Google Scholar 

  99. R. F. Atkins and P. R. Hammond, US Patent Application No. 630591; Chem. Abstr.,86, No. 7 43578 (1977).

    Google Scholar 

  100. O. S. Wolfbeis, Monatsh. Chem.,108, 499 (1977).

    Google Scholar 

  101. L. L. Woods and J. Sapp, J. Org. Chem.,27, 3703 (1962).

    Google Scholar 

  102. L. Shunyi, Kexue Tongbao,27, No. 12, 993 (1982); Chem. Abstr.,98, No. 12, 98470 (1983).

    Google Scholar 

  103. R. A. Henry, US Patent No. 4200753; Ref. Zh. Khim., 2N234P (1981).

  104. M. Patsch and F. Andree, West German Patent No. 2659698; Chem. Abstr.,89, No. 14, 112430 (1978).

    Google Scholar 

  105. E. R. Bissell, D. K. Larson, and M. C. Groudace, J. Chem. Eng. Data,26, No. 3, 348 (1981).

    Google Scholar 

  106. E. R. Bissell, Synthesis, No. 10, 846 (1982).

    Google Scholar 

  107. H. Harnisch, US Patent No. 4018796; Cl. 260-343.2R, C07D311/06.

  108. W. W. Williams and H. B. Freyermuth, US Patent No. 2680747; Chem. Abstr.,48, No. 16, 9702 (1954).

    Google Scholar 

  109. H. B. Appleton, West German Patent No. 1033218; Chem. Abstr.,55, No. 2, 1660 (1961).

    Google Scholar 

  110. H. Von Pechmann and M. Shaal, Chem. Ber.,32, 3690 (1899).

    Google Scholar 

  111. D. Möhlo and J. Aknin, Compt. Rend. Acad. Sci.,259, No. 9, 1645 (1964).

    Google Scholar 

  112. C. Bulow and T. Sprösser, Chem. Ber.,41, 487 (1908).

    Google Scholar 

  113. B. B. Dey, J. Chem. Soc.,107, 1606 (1915).

    Google Scholar 

  114. A. Knierzinger and O. S. Wolfbeis, J. Heterocycl. Chem.,17, No. 2, 225 (1980).

    Google Scholar 

  115. P. R. Hammond, E. J. Schmitschek, and J. A. Trias, US Patent Application No. 720175; Chem. Abstr.,86, No. 26, 197804 (1977).

    Google Scholar 

  116. H. Majerova, Czechoslovak Patent No. 140881; Chem. Abstr.,77, No. 10, 63353 (1972).

    Google Scholar 

  117. U. Claussen, West German Patent No. 2313030; Chem. Abstr., 82, No. 6, 32467 (1975).

    Google Scholar 

  118. Ja. Pirkl, Czechoslovak Patent No. 168107; Chem. Abstr.,87, No. 25, 201314 (1977).

    Google Scholar 

  119. Ja. Pirkl, Czechoslovak Patent No. 168121; Chem. Abstr.,87, No. 17, 135068 (1977).

    Google Scholar 

  120. R. S. Long and C. A. Sears, US Patent No. 2647133; Chem. Abstr.,47, No. 21, 1147 (1953).

    Google Scholar 

  121. R. S. Long and C. A. Sears, US Patent No. 2647132; Cl. 260-343.2.

  122. G. A. Reynolds, US Patent No. 3822270; US Patent No. 4005092; Chem. Abstr.,86, No. 22, 157047 (1977).

    Google Scholar 

  123. L. I. Smith and F. A. Culter, J. Org. Chem.,14, 740 (1949).

    Google Scholar 

  124. R. M. Mathur, Trans. Faraday Soc.,54, No. 431, Part 11, 1609 (1958).

    Google Scholar 

  125. G. Schoen and F. J. Marascia, US Patent No. 3030383; Chem. Abstr.,57, No. 7, 8551 (1962)

    Google Scholar 

  126. G. N. Kuverji and D. P. Ambalal, J. Chem. Soc., 1043 (1934).

  127. M. Machida, N. Ushijima, T. Takahashi, and Yu. Kanaoka, Chem. Pharm. Bull.,25, No. 6, 1289 (1977).

    Google Scholar 

  128. M. Ichikawa and H. Ichibagase, Yakugaku Zasshi,86, No. 11, 1064 (1966); Chem. Abstr.,66, No. 23, 104869 (1967).

    Google Scholar 

  129. H. Harnisch, West German Patent No. 2413281; Chem. Abstr.,84, No. 4, 19193 (1976).

    Google Scholar 

  130. H. Harnisch, West German Patent No. 2413371; Chem. Abstr.,84, No. 8, 46052 (1976).

    Google Scholar 

  131. R. S. Long and M. Scalera, US Patent No. 2844594; Chem. Abstr.,53, No. 4, 3718 (1959).

    Google Scholar 

  132. H. Imemoto, T. Kitao, and K. Konishi, Kogyo Kagaku Zasshi,73, No. 10, 2200 (1970); Chem. Abstr.,74, No. 12, 55115 (1971).

    Google Scholar 

  133. CIBA Ltd., Swiss Patent No. 265709; Chem. Abstr.,45, No. 10, 4270 (1951).

    Google Scholar 

  134. CIBA Ltd., Swiss Patent No. 265710; Chem. Abstr.,45, No. 10, 4270 (1951).

    Google Scholar 

  135. F. Ackermann, US Patent No. 2600375; Chem. Abstr.,47, No. 5, 2501 (1953).

    Google Scholar 

  136. Jo. Dehnert and G. Grau, West German Patent No. 1802863; Chem. Abstr.,73, No. 22, 110911 (1970).

    Google Scholar 

  137. P. Moeckli, West German Patent N0. 2844299; Chem. Abstr.,91, No. 6, 40902 (1979).

    Google Scholar 

  138. P. Moeckli, Dyes Pigm.,1, No. 1, 3 (1980); Chem. Abstr.,93, No. 20, 187730 (1980).

    Google Scholar 

  139. H. Harnisch, West German Patent No. 2925546; Chem. Abstr.,94, No. 22, 176685 (1981).

    Google Scholar 

  140. W. Mach and H. Scheuermann, West German Patent No. 2144591; Ref. Zh. Khim., 16N218P (1981)

  141. K. Bowden, M. J. Hanson, and G. R. Taylor, J. Chem. Soc., B, No. 2, 174 (1968).

    Google Scholar 

  142. K. Uekama, Ch.-L. Lin, F. Hirayama, M. Otagari, A. Takadata, and Sh. Goya, Chem. Lett., No. 4, 563 (1981).

    Google Scholar 

  143. C. W. Schellhammer, British Patent No. 1145966; Chem. Abstr.,71, No. 4, 14180 (1969).

    Google Scholar 

  144. A. Dolars, West German Patent No. 1906662; Chem. Abstr.,74, No. 4, 14197 (1971).

    Google Scholar 

  145. A. Dorlars and W. D. Wirth, US Patent No. 3839333; Chem. Abstr.,83, No. 14, 116987 (1975)

    Google Scholar 

  146. A. K. Sarkar, US Patent No. 3547952; Cl. 260-343.2, C07D7/28.

  147. H. Hausermann, US Patent No. 2945033; Chem. Abstr.,55, No. 3, 3082–3084 (1961).

    Google Scholar 

  148. Farbenfabriken Bayer A.-G., Netherlands Patent No. 405139; Chem. Abstr.,62, No. 13, 16424 (1965).

    Google Scholar 

  149. C. W. Schellhammer, E. Degener, H. G. Schmelzer, and A. Wagner, French Patent No. 1395233; Chem. Abstr.,63, No. 5, 5796 (1965).

    Google Scholar 

  150. E. I. Du Pont de Nemours and Co., West German Patent No. 999780; Chem. Abstr.,69, No. 12, 47409 (1968).

    Google Scholar 

  151. J. R. Geigy A.-G., Netherlands Patent No. 6603113; Chem. Abstr.,66, No. 15, 66742 (1967).

    Google Scholar 

  152. G. F. D'Alelio, US Patent No. 3304346; Chem. Abstr.,66, No. 20, 86764 (1967).

    Google Scholar 

  153. Showa Chemical Industries, Ltds., French Patent No. 1583335; Chem. Abstr.,73, No. 20, 100075 (1970).

    Google Scholar 

  154. K. Suzuki, Japanese Patent No. 01896; Chem. Abstr.,72, No. 24, 122937 (1970).

    Google Scholar 

  155. K. Suzuki, Japanese Patent No. 17448; Chem. Abstr.,77, No. 26, 166174 (1972).

    Google Scholar 

  156. K. Suzuki, Japanese Patent No. 17423; Chem. Abstr.,81, No. 16, 93088 (1974).

    Google Scholar 

  157. K. Suzuki, Japanese Patent No. 35394; Chem. Abstr.,75, No. 8, 50425 (1971).

    Google Scholar 

  158. K. Suzuki, Japanese Patent No. 31391; Chem. Abstr.,78, No. 12, 73666 (1973).

    Google Scholar 

  159. J. P. Weiss and E. D. Smith, US Patent No. 4028550; Chem. Abstr.,87, No. 6, 47203 (1977).

    Google Scholar 

  160. E. I. Du Pont Nemours and Co., West German Patent No. 1541300; Chem. Abstr.,91, No. 10, 81495 (1979).

    Google Scholar 

  161. R. D. Haworth, A. H. Lamberton, and D. Woodcock, J. Chem. Soc., 182 (1947).

  162. CIBA Ltd., Swiss Patent No. 265711; Chem. Abstr.,45, No. 10, 4270 (1951).

    Google Scholar 

  163. CIBA Ltd., Swiss Patent No. 265715; Chem. Abstr.,45, No. 10, 4270 (1951).

    Google Scholar 

  164. K. H. Boltze, P. R. Seidel, H. Jacobi, and H. D. Dell, West German Patent No. 2448257; Chem. Abstr.,85, No. 5, 32846 (1976).

    Google Scholar 

  165. H. Haeusermann, Swiss Patent No. 373403; Chem. Abstr.,61, No. 5, 5828 (1964).

    Google Scholar 

  166. M. Yalapani and L. D. Hall, Can. J. Chem.,59, No. 20, 2934 (1981).

    Google Scholar 

  167. Farbenfabriken Bayer A.-G., British Patent No. 748884; Chem. Abstr.,50, No. 21, 15246 (1956).

    Google Scholar 

  168. CIBA Ltds., Swiss Patent No. 265712; Chem. Abstr.,45, No. 10, 4270 (1951).

    Google Scholar 

  169. W. I. Lyness, R. T. Amel, and G. E. Booth, US Patent No. 3828060; Chem. Abstr.,81, No. 20, 122804 (1974).

    Google Scholar 

  170. Showa Chemical Industries, Ltd., Japanese Patent No. 140990; Chem. Abstr.,96, No. 11, 85311 (1981).

    Google Scholar 

  171. F. Seng, U. Claussen, G. Beck, and K. Sasse, European Patent No. 3229301; Cl. C07D417/04; Chem. Abstr.,101, 8712 (1984).

    Google Scholar 

  172. S. Dengler, P. Loew, Ch. Zickendraht, and H. Schwander, West German Patent No. 2430980; Chem. Abstr.,83, No. 4, 29876 (1975).

    Google Scholar 

  173. CIBA Ltds., Swiss Patent No. 260835; Chem. Abstr.,44, No. 13, 6160 (1950).

    Google Scholar 

  174. CIBA Ltds., Swiss Patent No. 265707; Chem. Abstr.,45, No. 10, 4270 (1951).

    Google Scholar 

  175. CIBA Ltds., Swiss Patent No. 265708; Chem. Abstr.,45, No. 10, 4270 (1951).

    Google Scholar 

  176. CIBA Ltds., Swiss Patent No. 265713; Chem. Abstr.,45, No. 10, 4270 (1951).

    Google Scholar 

  177. H. Harnisch, West German Patent No. 2300488; Chem. Abstr.,82, No. 4, 18628 (1975).

    Google Scholar 

  178. A. Dorlars and W. D. Wirth, Republic of South Africa Patent No. 6808154; Chem. Abstr.,72, No. 22, 112806 (1970).

    Google Scholar 

  179. A. Dorlars, C. W. Schellhammer, and J. Schroeder, West German Patent No. 2816028; Cl. C07D405/10.

  180. R. Kirchmayr and J. Rody, West German Patent No. 1936760; Chem. Abstr.,73, No. 6, 26625 (1970).

    Google Scholar 

  181. Yu. Kanoaka, T. Takahashi, and H. Nakayama, Chem. Pharm. Bull.,25, No. 2, 362 (1977).

    Google Scholar 

  182. E. Prusak, M. Siewinski, and A. Szewczuk, Clin. Chim. Acts,107, Nos. 1–2, 21 (1980); Chem. Abstrs.,94, No. 3, 12009 (1981).

    Google Scholar 

  183. Sh. Sakakibara, US Patent No. 4237047; Ref. Zh. Khim., 15021P (1981).

  184. K. Murakami, T. Osawa, Sh. Hirose, K. Takada, and Sh. Sakakibara, Anal. Biochem.,110, No. 1, 232 (1981); Chem. Abstr.,94, No. 11, 79045 (1981).

    Google Scholar 

  185. Yu. Kanaoka, T. Takahashi, H. Nakayama, T. Ueno, and T. Sekine, Chem. Pharm. Bull.,30, No. 4, 1485 (1982).

    Google Scholar 

  186. Torii and Co., Ltd., Japanese Patent No. 75956; Chem. Abstr.,97, No. 19, 163507 (1982).

    Google Scholar 

  187. G. A. Reynolds and K. H. Drexhage, Opt. Commun.,13, No. 3, 222 (1975).

    Google Scholar 

  188. F. P. Schaefer (editor), Dye Lasers, Sringer-Verlag (1974).

  189. K. H. Drexhage, J. Res. Natl. Bur. Stand.,80A, No. 3, 421 (1976).

    Google Scholar 

  190. M. I. Dzyubenko, V. V. Maslov, N. G. Naumenko, V. M. Nikitchenko, and V. P. Pelipenko, Opt. Spektrosk.,45, No. 4, 814 (1978).

    Google Scholar 

  191. B. Cnavelj, O. J. Petersen, and R. F. Reithel, US Patent NO. 3521187; Cl. 331-94.5, H01S3/00.

  192. L. K. Denisov, N. A. Kozlov, and B. M. Uzhinov, in: Reviews on Electronic Technology [in Russian], Ser. IV, No. 8(686), “élektronika” Central Scientific-Research Institute, Moscow (1979–1980).

    Google Scholar 

  193. P. R. Hammond, R. E. Cshimischek, and J. A. Trias, US Patent No. 4051062; Cl. 252/301.7, H01S3/20, F 21 k 2/00.

  194. N. A. Borisevich, L. M. Bolot'ko, V. V. Gruzinskii, and V. A. Tolkachev, Zh. Prikl. Spektrosk.,14, 148 (1971).

    Google Scholar 

  195. M. I. Dzyubenko, N. G. Naumenko, V. P. Pelipenko, and S. E. Soldatenko, Pis'ma Zh. éksp. Teor. Fiz.,18, No. 1, 43 (1973).

    Google Scholar 

  196. V. A. Alekseev, L. K. Denisov, N. A. Kozlov, V. N. Makarov, and L. M. Mel'nikova, in: Summaries of Papers Presented at the 7th All-Union Conference on Coherent and Nonlinear Optics [in Russian], Vol. 1, Tbilisi (1976), p. 98.

    Google Scholar 

  197. “Blue-green dye laser emerges as dark horses for links to submarines,” Laser Focus,17, No. 10, pp. 12, 14, 16 (1981).

  198. S. A. Tucio, K. H. Drexhage, and G. A. Reynolds, Opt. Commun.,7, No. 3, 248 (1973).

    Google Scholar 

  199. R. F. Kubin and A. N. Fletcher, Chem. Phys. Lett.,99, No. 1, 49 (1983).

    Google Scholar 

  200. N. A. Borisevich, V. V. Gruzinskii, N. M. Paltarak and P. I. Petrovich, Zh. Prikl. Spektrosk.,12, 926 (1970).

    Google Scholar 

  201. M. I. Dzyubenko G. S. Volotyka, V. V. Maslov, and V. M. Nikitchenko, Opt. Spektrosk.,34, No. 3, 554 (1975).

    Google Scholar 

  202. M. R. Padnye, T. S. Varadarajan, and A. Deshpaude, Spectrosc. Lett.,15, No. 8, 597 (1982)

    Google Scholar 

  203. Yu. G. Basov, L. K. Denisov, V. S. Zuev, O. A. Logunov, V. M. Nikitenko, A. V. Startsev, and Yu. Yu. Stoilov, Kvantovaya Elektron.,8, No. 6, 1306 (1981).

    Google Scholar 

  204. O. A. Logunov, A. V. Startsev, and Yu. Yu. Stoilov, Kvantovaya élektron.,8, No. 6, 1307 (1981).

    Google Scholar 

  205. N. G. Basov, O. A. Logunov, D. Kh. Nurligareev, and K. K. Trusov, Kvantovaya, élektron.,8, No. 10, 2283 (1981).

    Google Scholar 

  206. K. K. Trusov, Kvantovaya élektronik.,9, No. 11, 2192 (1982).

    Google Scholar 

  207. J. B. Marling, L. L. Wood, and D. W. Gregg, IEEE, J. Quant. Electron., 498 (1971).

  208. V. A. Mostovnikov, A. N. Rubinov, S. S. Anufrin, G. R. Ginevich, V. M. Nikitchenko, and G. S. Volotyka, Zh. Prikl. Spektrosk.,27, 59 (1977).

    Google Scholar 

  209. J. C. Mialocg and P. Goujon, Appl. Phys. Lett.,33, No. 9, 819 (1978).

    Google Scholar 

  210. W. Sibbett and J. R. Taylor, Opt. Commun.,46, No. 1, 32 (1983).

    Google Scholar 

  211. W. Sibbett and J. R. Taylor, Appl. Phys. Lett.,29, No. 3, 191 (1982).

    Google Scholar 

  212. N. A. Borisevich, V. V. Gruzinskii, N. M. Paltarak, L. P. Snagoshchenko, and V. A. Suchkov, Zh. Prikl. Spektrosk.,14, 41 (1971).

    Google Scholar 

  213. K. Takahashi and H. Kusakawa, Mitsubishi Denki Giho,48, No. 5, 646 (1974).

    Google Scholar 

  214. S. A. Krashakov, A. I. Akimov, N. V. Korol'kova, L. K. Denisov, and B. M. Uzhinov, Zh. Prikl. Spektrosk.,40, 52 (1984).

    Google Scholar 

  215. A. N. Fletcher, D. E. Bliss, and J. M. Kauffman, Opt. Commun.,47, No. 1, 57 (1983).

    Google Scholar 

  216. K. H. Drexhage, G. R. Erikson, G. H. Hawks, and G. A. Reynolds, Opt. Commun.,15, No. 3, 399 (1975).

    Google Scholar 

  217. J. Von Trebra and T. H. Koch, Appl. Phys. Lett.,42, No. 2, 129 (1983).

    Google Scholar 

  218. A. N. Fletcher and D. E. Bliss, Appl. Phys.,16, 289 (1978).

    Google Scholar 

  219. A. N. Fletcher, Appl. Phys.,16, 93 (1978).

    Google Scholar 

  220. B. H. Winters, H. J. Mandelberg, and W. B. Mohr, Appl. Phys. Lett.,25, No. 12, 723 (197.

  221. A. N. Fletcher, Appl. Phys.,14, 295 (1977).

    Google Scholar 

  222. E. J. Schimitshek, J. A. Trias, M. Taylor, and J. E. Celto, IEEE J. Quant. Electron.,9, No. 7, 781 (1973).

    Google Scholar 

  223. E. J. Schimitschek, J. A. Triass, P. R. Hammond, R. A. Henry, and R. L. Atkins, Opt. Commun.,16, No. 3, 313 (1976).

    Google Scholar 

  224. A. N. Fletcher, R. H. Knipe, and H. E. Pietrak, Appl. Phys.,27, No. 2, 93 (1982).

    Google Scholar 

  225. E. J. Schimitschek, J. A. Triass, P. R. Hammond, and R. L. Atkins, Opt. Commun.,11, No. 4, 352 (1974).

    Google Scholar 

  226. J. Von Trebra and T. H. Koch, Chem. Phys. Lett.,93, No. 4, 315 (1982).

    Google Scholar 

  227. J. C. Messager and Y. Delugeard, Cryst. Struct. Commun., 3(3), 391 (1974); Chem. Abstr.,81, No. 12, 69708 (1974).

    Google Scholar 

  228. L. S. Shibryaeva, A. I. Mikaya, and V. G. Zaikin, Zh. Obshch. Khim.,50, No. 4, 940 (1980)

    Google Scholar 

  229. L. S. Shibryaeva, A. I. Mikaya, R. L. Ushakova, and V. G. Zaikin, Zh. Obshch. Khim.,50, No. 11, 2607 (1980).

    Google Scholar 

  230. O. S. Wolfbreis and G. Uray, Monatsh. Chem.,109, No. 1, 123 (1978).

    Google Scholar 

  231. S. A. Sojka, J. Org. Chem.,40, No. 8, 1175 (1975).

    Google Scholar 

  232. M. A. Kirpichenok, I. I. Grandberg, L. K. Denisov, and L. M. Mel'nikova, Izv. Timiryazev Sel'skokhoz. Akad., No. 3, 172 (1985).

    Google Scholar 

  233. R. A. De Lima, F. Ferrari, F. delie Monache, and G. B. Marini-Bettole, Atti Acad. Naz. Lincei, Rend. Classe Sci. Fiz. Mat. Nat.,60, 633 (1976).

    Google Scholar 

  234. H. E. Gottlieb, A. R. de Lima, and F. delie Monache, J. Chem. Soc., Perkin Trans. 2, No. 4, 435 (1979).

    Google Scholar 

  235. A. Engelmann, West German Patent (Offen.) No. 2910592; Ref. Zh. Khim., 15N196P (1981).

  236. W. Koch, US Patent No. 3880886; Cl. 260-343.2R, C07D7/26.

  237. H. Scheuermann and D. Augart, US Patent No. 3985772; CL. 260-343.2, C07D311/74.

  238. U. Eckstein, R. Raue, and C. W. Schellhammer, West German Patent (Offen.) No. 2902470; Ref. Zh. Khim., 9N239P (1981).

Download references

Author information

Authors and Affiliations

Authors

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 147–174, February, 1987.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Grandberg, I.I., Denisov, L.K. & Popova, O.A. 7-Aminocoumarins (Review). Chem Heterocycl Compd 23, 117–142 (1987). https://doi.org/10.1007/BF00663848

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00663848

Keywords

Navigation