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Synthesis of Heterocycles

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Catalytic Reductive Carbonylation of Organic Nitro Compounds

Part of the book series: Catalysis by Metal Complexes ((CMCO,volume 20))

Abstract

The synthesis of carbamates and isocyanates via the catalytic carbonylation of organic nitro compounds (Chapters 2 and 3) is still not competitive with respect to the classical phosgene route. However, this is true if we consider only the cost of the reagents and the complexity of the equipment required by the two alternative routes. We are now living in a time in which environmentally friendly processes are required and, when evaluating alternative routes to a product, both the amount and the nature of the waste make a difference [1]. Moreover, chlorine-based chemistry is currently under fire from those concerned about its potential environmental impact [2]. When chlorine is a reagent which does not appear in the product, an alternative route is becoming highly desirable. Anyhow, being the present situation still an equilibrium between the need for a safe process and the appeal of an old, low cost process, there has recently been an increasing interest in deeply investigating the potential utility of the catalytic carbonylation of organic nitro compounds in the synthesis of fine chemicals such as heterocycles. The assumption is that the synthesis of such expensive compounds, which is usually done in low amounts, should better tolerate the use of precious metals as catalysts.

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References

  1. Sheldon, R.A. CHEAITECH (March, 1994) 38.

    Google Scholar 

  2. Hileman, B. Chem.Eng.News (April 19, 1993 ) 11.

    Google Scholar 

  3. Kmiecik, J.E. J.Org.Chem. 30 (1965) 2014.

    Article  CAS  Google Scholar 

  4. Alper, H. and Edwards, J.T. Can.J.Chem. 48 (1970) 1543.

    Article  CAS  Google Scholar 

  5. Cadogan, J.I.G.and Cameron-Wood, M. Proc.Chem.Soc. (1962) 361.

    Google Scholar 

  6. Bunyan, P.J. and Cadogan, J.I.G. J.Chem.Soc. (1963) 42.

    Google Scholar 

  7. Cadogan, J.I.G.and Searle, R.J.G. Chem.Lul.(London) (1963) 1434.

    Google Scholar 

  8. Smith, P.A.S., in Nitrenes, W. Lwowski (ed.), Interscience Publishers, New York (1970) p. 134.

    Google Scholar 

  9. Crotti, C., Cenini, S., Bassoli, A., Rindone, B., and Demartin, F. J.AIol.Catal. 70 ( 1991 175.

    Article  CAS  Google Scholar 

  10. Sappa, E. and Milone, L. J.Organomet.Chem. 61 (1973) 383.

    Article  CAS  Google Scholar 

  11. Smieja, J.A.and Gladfelter, W.L. Lzorg.Chem. 25 (1986) 2667.

    Google Scholar 

  12. Han, S.-I-I., Geoffroy, G.L., and Rheingold, A.L. Inorg.Chem. 26 (1987) 3426.

    Article  CAS  Google Scholar 

  13. Noble, W.L., in Highlights of Organic Chemistry, P.G. Gassman (ed.), Marcel Dekker New York (1974), p. 612.

    Google Scholar 

  14. Bassoli, A., Cenini, S., Farina, F., Orlandi, M., and Rindone, B. J.AIol.Catal. 89 (1994) 121.

    Article  CAS  Google Scholar 

  15. Han, S.-IT., Geoffroy, G.L., Dombek, B.D., and Rheingold, A.L. Inorg.Chem. 27 ( 1988 4355.

    Article  CAS  Google Scholar 

  16. Ilan, S.-H-, Song, J.-S., Macklin, P.D., Nguyen, S.T., GeolTroy, G.I,., and Rheingold, Al.. Organontetcrllics 8 (1989) 2127.

    Google Scholar 

  17. Ramage, 1).L., Geoffroy, G.L., Rheingold, A.L., and Ilaggerty, B.S. Orgcmonretallies 1 (1992) 1242.

    Google Scholar 

  18. Rivonnanata, S., Lavigne, G., Lugan, N., and Bonnet, J.-J. Organornetallics 10 (1991) 2285.

    Google Scholar 

  19. Pizzotti, M., Cenini, S., Quid, S., and Tollari, S. J.(’hent.Soc.Perkin Trans. 2 ( 1994 913.

    Article  Google Scholar 

  20. Ragaini, F., Chilli, A., Cenini, S. unpublished results

    Google Scholar 

  21. For a survey of these reactions see also: Lavigne, G., in The Chemistry of Metal Cluste Complexes, D.F. Shriver, H.D. Kacsz and R.A. Adams (eds.), VCI-i Publishers, Inc., Ne York (1990), p. 201.

    Google Scholar 

  22. Cenini, S., Pizzotti, M., Crotti, C., Porta, F., and La Monica, G J.Chem.Soc., Chem.Comnnut. (1984) 1286.

    Google Scholar 

  23. Cenini, S., Crotti, C., Pizzotti, M., and Porta, F. J.Org.Chem. 53 (1988) 1243.

    Article  CAS  Google Scholar 

  24. Braca, G. and Sbrana, S., in Aspects of Homogeneous Catalysis, R. Ugo (ed.), Reidel Dordrecht (1994),Vol. 5, p. 269.

    Google Scholar 

  25. Hegedus, L.S. Angew.Chem.Int.Ed.Engl. 27 (1988) 1113 and references therein.

    Google Scholar 

  26. Crotti, C., Cenini, S., Rindone, B., Tollari, S., and Demartin, F J.Chem.Soc., Chenr.Commun. (1986) 784.

    Google Scholar 

  27. Ucciani, E. and Bonfand, A. J.Chem.Soc., Chem.Commmn. (1981) 82.

    Google Scholar 

  28. Tufariello, J.J., Nitrones,in 1–3-Dipolar Cycloaddition Chemistry,A. Padwa (ed.), Job Wiley and Sons, New York (1984), Vol. 2.

    Google Scholar 

  29. Porta, F., Pizzotti, M., and Cenini, S. J.Organomet.Chenr. 222 (1981) 279.

    Google Scholar 

  30. Crotti, C., Cenini, S., Todeschini, R., and Tollari, S. J.Chent.Soc.Faraday Trans. 8 (1991) 2811.

    Google Scholar 

  31. Laine, R.M. J.AIoI.Catal. 14 (1982) 137.

    Article  CAS  Google Scholar 

  32. Bor, G. Pure Appl.Chem. 58 (1986) 543.

    Article  CAS  Google Scholar 

  33. Koelliker, R. and Bor, G. J.Organomet.Chem. 417 (1991) 439.

    Article  CAS  Google Scholar 

  34. Akazome, M., Kondo, T., and Watamabe, Y. Chem.Lett. (1992) 769.

    Google Scholar 

  35. Akazome, M., Kondo, T., and Watamabe, Y. J.Org.Chen. 59 (1994) 3375.

    Article  CAS  Google Scholar 

  36. Tollari, S., Cenini, S., Crotti, C., and Giannella, E. J.AIo/.Catal. 87 (1994) 203.

    Article  CAS  Google Scholar 

  37. Cenini, S., Ragaini, F., Pizzotti, M., Porta, F., Mestroni, G., and Alcssio, E. J11Io1.Catal 64 (1991) 179.

    CAS  Google Scholar 

  38. Cenini, S., Bettettini, E., Fedele, M., and Tollari, S. J.Aiol.Catcrl. submitted.

    Google Scholar 

  39. Buchardt, O., Duffield, A.M., and Shapiro, R.H. Tetrahedron 24 (1968) 3139.

    Article  CAS  Google Scholar 

  40. Leconte, P., Metz, F., Mortreux, A., Osborn, J.A., Paul, F., Petit, F., and Pillot, A J.Chem.Soc., Chem.Commun. (1990) 1616.

    Google Scholar 

  41. Ugo, R., Psaro, R., Pizzotti, M., Nardi, P., Dossi, C., Andreetta, A., and Capparella, G J.Organontet.C’henr. 417 (1991) 211.

    Article  CAS  Google Scholar 

  42. Iddon, B., Meth-Cohn, O., Scriven, E.F.V., Suschitzky, H., and Gallager, P.T Angew.Chem.Int.Ed.Engl. 18 (1979) 900.

    Google Scholar 

  43. Sundberg, R.J. J.Org.Chem. 30 (1965) 3604.

    Article  CAS  Google Scholar 

  44. Sundberg, R.J. J.Org.Chem. 33 (1968) 487.

    Article  CAS  Google Scholar 

  45. Sundberg, R.J. and Yamazaki, T. J.Org.Chem. 32 (1967) 290.

    Article  CAS  Google Scholar 

  46. Sundberg, R.J., Russel, H.F., Ligon, W.F., and Lin, L.-S. J.Org.Chemt. 37 (1972) 719.

    Article  CAS  Google Scholar 

  47. Cadogan, J.I.G., Cameron-Wood, M., Mackie, R.K., and Searle, R.J.G. J.Chem.Soc (1965) 4831.

    Google Scholar 

  48. Crotti, C., Cenini, S., Ragaini, F., Porta, F., and Tollari, S. J.Mo1.Catal. 72 (1992) 283.

    Article  CAS  Google Scholar 

  49. Wright, J.B. Chem.Rev. 48 (1951) 397.

    Article  CAS  Google Scholar 

  50. Marshall, M., Sears, D.J., and Smith, D.M. J.Chem.Soc.(C) (1970) 2144.

    Google Scholar 

  51. Venalainen, T., Iiskola, E., Pakkanen, T.A., and Pakkanen, T.T. J.AIol.Catal. 34 ( 1986 305.

    Article  CAS  Google Scholar 

  52. Akazome, M., Kondo, T., and Watanabe, Y. J.Chem.Soc., Chem.Conrmnn. (1991) 1466.

    Google Scholar 

  53. Pizzotti, M., Cenini, S., Psaro, R., and Costanzi, S. J.AIol.CataL 63 (1990) 299.

    Article  CAS  Google Scholar 

  54. Basu, A., Bhaduri, S., and Khwaja, H. J.Organomet.Chem. 319 (1987) C28.

    Article  CAS  Google Scholar 

  55. Bhaduri, S., Sharma, K., Kalpathi, G.S. U.S. US 4,491,670 (1985). Chem.Abstr. 102:166489r.

    Google Scholar 

  56. Mise, T., Hong, P., and Yamazaki, H. Chem.Lett. (1980) 439.

    Google Scholar 

  57. Institute of Phisycal and Chemical Research Jpn.Kokai Tokkyo Koho JP 81,138,15 (1981). Chem.Abstr.: 96:68634x.

    Google Scholar 

  58. Hong, P., Yamazaki, H., Sonogashira, K., and Hagihara, N. Chem.Lett. (1978) 535.

    Google Scholar 

  59. Bader, R., Kueng, L., and Waldvogel, P. Ger.Ofen. 2,835,529 (1979). Chem.Abstr. 90:186959f. (Equivalent to U.S. US 4,220,788 (1980)).

    Google Scholar 

  60. Shen, J.-K., Shi, Y.-L., Gao, Y.-C., Shi, Q.-Z., and Basolo, F. J.Am.Chem.Soc. 11 (1988) 2414.

    Article  Google Scholar 

  61. Smieja, J.A., Gomm, J.E., and Gladfelter, W.L. Organometallics 6 (1987) 1311.

    Article  CAS  Google Scholar 

  62. Bruce, M.I., Humphrey, M.G., bin Shawkataly, O., Snow, M.R., and Tiekink, R.T J.Organomet.Chem. 336 (1987) 199.

    Article  CAS  Google Scholar 

  63. Pizzotti, M., Ragaini, F., and Cenini, S. Gazz.Chim.Ital. 123 (1993) 683.

    CAS  Google Scholar 

  64. Pizzotti, M., Ragaini, F., Cenini, S., and Costanzi, S. Ital.Pat.Appl. MI 91A 00091 (1991).

    Google Scholar 

  65. Cadogan, J.I.G., Mackie, R.K., and Todd, M.J. J.Chem.Soc., Chem.Connmmt. (1965) 491.

    Google Scholar 

  66. Braustein, P., Kervennal, J., and Richter, J.-L. Angew.Chem.Lnt.Ed.Engl. 24 (1985) 768.

    Google Scholar 

  67. Braustein, P., Kervennal, J., and Richter, J.-L., and Ries, M. Eur.Pat.Appl. EP 150,13 (1985). Chem.Abstr.: 104: 19681k.

    Google Scholar 

  68. Braustein, P., Devenish, R., Gallezot, P., Heaton, B.T., Humphreys, C.J., Kervennal, J. Mulley, S., and Ries, M. Angew.Chem.bn.Ed.Engl. 27 (1988) 927.

    Article  Google Scholar 

  69. Drent, E. Eur. Pat. Appl. EP 255, 744 (1988).

    Google Scholar 

  70. Drent, E. Chem.Abstr: 108:150461p.

    Google Scholar 

  71. Nagase Kasei Kogyo, K.K. Jpn.Kokai Tokkyo Koho JP 58,225,072 [83, 225,072] (1983) Chem.Abstr.: 100:209794q.

    Google Scholar 

  72. Osaka Prefecture Jpn.Kokai Tokkyo Koho JP 82,102,876 (1982). Chem.Abstr. 97:162968b.

    Google Scholar 

  73. Hirashima, T., Miyata, T., Yamamoto, Y., and Kato, M. Demande FR 2,485,01 (1981). Chem.Abstr.: 96: 18 1288a.

    Google Scholar 

  74. Iqbal, A.F.M. Helv.Chim.Acta. 55 (1972) 798.

    Article  CAS  Google Scholar 

  75. Igbal, A.F.M. J.Org.Chem. 37 (1972) 2791.

    Article  Google Scholar 

  76. Iqbal, A.F.M. Angew.Chern.Int.Ed.Engl. 11 (1972) 634.

    Article  CAS  Google Scholar 

  77. Igbal, A.F.M. CHEMTECH (1974) 566.

    Google Scholar 

  78. Mohan, A.G. J.Org.Chem. 35 (1970) 3982.

    Article  CAS  Google Scholar 

  79. Falbe, J. Angew.Chem.Int.Ed.Engl. 5 (1966) 435.

    Article  CAS  Google Scholar 

  80. Falbe, J., Korte, F. Brennstoffchemie 46 (1965) 276.

    Google Scholar 

  81. I. Wender and P. Pino (eds.), Organic Synthesis via Metal Carbonyls,John Wiley an Sons, New York (1977), Vol.2.

    Google Scholar 

  82. Alper, H. and Edwards, J. T. J.Org.Chem. 32 (1967) 2938.

    Google Scholar 

  83. Boyle, W.J.,Jr. and Mares, F. Organometallics 1 (1982) 1003.

    Google Scholar 

  84. Lion, K.F. and Cheng, C.H. J.Org.Chem. 47 (1982) 3018.

    Article  Google Scholar 

  85. Watanabe, Y., Tsuji, Y., and Suzuki, N. Chem.Lett. (1981) 1067.

    Google Scholar 

  86. Watanabe, Y., Suzuki, N., Shim, S.C., Yamamoto, M., Mitsudo, T., and Takegami, Y Chem.Lett. (1980) 429.

    Google Scholar 

  87. Watanabe, Y., Suzuki, N., Tsuji, Y., Shim, S.C., and Mitsudo, T. Bull.Chem.Soc.Jpn. 5 (1982) 1116.

    Article  Google Scholar 

  88. Watanabe, Y., Takatsuki, K., Shim, S.C., Mitsudo, T., and Takegami, Y BnlCChem.Snc.Jpn. 51 (1978) 3397.

    Article  CAS  Google Scholar 

  89. A. Weissberger and E.C. Taylor, The Chemistry of Heterocyclic Compounds. Ouinolines Part I,John Wiley and Sons, New York (1977), Vol.32.

    Google Scholar 

  90. Watanabe, Y., Suzuki, N., and Tsuji, Y. Bul1.Chenr.Soe.JpW. 55 (1982) 2445.

    CAS  Google Scholar 

  91. Akazome, M., Kondo, T., and Watanabe, Y. J.Otg;.Chem. 58 (1993) 310.

    Article  CAS  Google Scholar 

  92. W.A. Nugent and J.M. Mayer, Metal-Ligand Multiple Bonds, Wiley Interscience, Ne York (1988).

    Google Scholar 

  93. Cenini, S., Console, S., Crotti, C., and Tollari, S. J.Organomet.Chem. 451 (1993) 157.

    Article  CAS  Google Scholar 

  94. Drent, E., Van Leeuwen, P.W.N.M. Eur.Pat.Appl. EP 86,281 (1983). Cheni.Abstr. 100: 6109x.

    Google Scholar 

  95. Leconte, P.and Metz, F. Eur.Pat.Appl. EP 330,591 (1988). Chem.Ahstr.: 112: 78160c.

    Google Scholar 

  96. Bernardi, L., Coda, S., Bonsignori, A., Pegrassi, L., and Suchowsky, G.K. Experientia 2 (1969) 787.

    Article  Google Scholar 

  97. Cenini, S., Pizzotti, M. and Crotti, C., in Aspects of Homogeneous Catalysis, R. Ugo (ed.) Reidel Publishing Company, Dordrecht (1988), p. 97.

    Google Scholar 

  98. Bhaduri, S., Gopalkrislman, K.S., Clegg, W., Jones, P.G., Sheldrick, G.M., and Stalke, D J.Chem.Soc.Dalton Trans. (1984) 1765.

    Google Scholar 

  99. Bassoli, A., Rindone, B., Tollari, S., Cenini, S., and Crotti, C. J.A1ol.Catal. 52 ( 1989 L45.

    Article  CAS  Google Scholar 

  100. Tollari, S., Cenini, S., Ragaini, F., and Cassar, L. J.Chem.Soc., Chem.Commun. ( 1994 1741.

    Google Scholar 

  101. Kalinin, V.N., Shostakovsky, M.V., and Ponomaryov, A.B. Tetrahedron Lett. 33 ( 1992 373.

    Article  CAS  Google Scholar 

  102. Ragaini, F., Cenini, S., and Tollari, S. J.Afol.Catal. 85 (1993) Ll.

    Google Scholar 

  103. Annunziata, R., Cenini, S., Palmisano, G., and Tollari, S. Synthetic Commun. 26 ( 1996 495.

    Article  CAS  Google Scholar 

  104. Akazome, M., Yamamoto, J., Kondo, T., and Watanabe, Y. J.Otganomet.Chem. 49 (1995) 229.

    Article  Google Scholar 

  105. Adachi, K. J.Pharm.Soc.Jpn. 75 (1955) 1423.

    CAS  Google Scholar 

  106. Itoh, K., Nakanishi, S., and Otsuji, Y. Bu ll.Chem.Soc.Jpn. 64 (1991) 118.

    Article  CAS  Google Scholar 

  107. Watanabe, Y., Yamamoto, J., Akazome, M., Kondo, T., and Mitsudo, T. J.Otg.Chem. 6 (1995) 8328.

    Article  Google Scholar 

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  1. Dipartimento di Chimica Inorganica, Metallorganica e Analitica, Universita degli Studi di Milano, Milan, Italy

    Sergio Cenini & Fabio Ragaini

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  1. Sergio Cenini
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  2. Fabio Ragaini
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Cenini, S., Ragaini, F. (1997). Synthesis of Heterocycles. In: Catalytic Reductive Carbonylation of Organic Nitro Compounds. Catalysis by Metal Complexes, vol 20. Springer, Dordrecht. https://doi.org/10.1007/978-94-017-0986-6_5

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  • DOI: https://doi.org/10.1007/978-94-017-0986-6_5

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