Monatshefte für Chemie - Chemical Monthly

, Volume 141, Issue 11, pp 1159–1182

Recent developments in benzotriazole methodology for construction of pharmacologically important heterocyclic skeletons

  • Raju R. Kale
  • Virendra Prasad
  • Prabhu P. Mohapatra
  • Vinod K. Tiwari
Review

Abstract

Benzotriazole methodology, nowadays recognized as a versatile, useful, and most successful synthesis protocol, has grown from an obscure level to very high popularity, since benzotriazole can easily be introduced into a molecule by a variety of reactions, activates it toward numerous transformations, is sufficiently stable during the course of reactions, and finally can easily be removed at the end of the reaction sequence. In this review, we briefly describe the way benzotriazole methodology has grown to its present height, the opportunities and its potentiality in the synthesis of diverse pharmacologically important heterocyclic skeletons.

Graphical abstract

Keywords

Heterocycles Benzotriazole Cyclization Ylide 

References

  1. 1.
    Katritzky AR, Lan X, Jason Z, Yang Z, Denisko OV (1998) Chem Rev 98:409CrossRefGoogle Scholar
  2. 2.
    Katritzky AR, Manju K, Singh SK, Meher NK (2005) Tetrahedron 61:2555CrossRefGoogle Scholar
  3. 3.
    Katritzky AR, Rogovoy BV (2003) Chem Eur J 19:4586CrossRefGoogle Scholar
  4. 4.
    Katritzky AR, Belyakov SA (1998) Aldrichimica Acta 31:35Google Scholar
  5. 5.
    Katritzky AR (2000) Pure Appl Chem 2:597Google Scholar
  6. 6.
    Katritzky AR, Toader D (2001) Synlett 4:458Google Scholar
  7. 7.
    Katritzky AR, Lan X (1994) Chem Soc Rev 23:363CrossRefGoogle Scholar
  8. 8.
    Katritzky AR, Lan X, Fan WQ (1994) Synthesis 445Google Scholar
  9. 9.
    Katritzky AR, Henderson SA, Yang B (1998) J Heterocycl Chem 35:1123CrossRefGoogle Scholar
  10. 10.
    Katritzky AR (1999) J Heterocycl Chem 36:1501CrossRefGoogle Scholar
  11. 11.
    Katritzky AR, Li J, Xie L (1999) Tetrahedron 55:8263CrossRefGoogle Scholar
  12. 12.
    Katritzky AR, Qi M (1998) Collect Czech Chem Commun 63:599CrossRefGoogle Scholar
  13. 13.
    Katritzky AR, Qi M (1998) Tetrahedron 54:2647CrossRefGoogle Scholar
  14. 14.
    Katritzky AR, Suzuki K, Wang Z (2005) Synlett 11:1656CrossRefGoogle Scholar
  15. 15.
    Katritzky AR, Kim MS, Widyana K (2008) Arkivoc iii:91Google Scholar
  16. 16.
    Verma AK, Singh J, Chaudhary R (2007) Tetrahedron Lett 48:7199CrossRefGoogle Scholar
  17. 17.
    Verma AK, Singh J, Sankar VK, Chaudhary R, Chandra R (2007) Tetrahedron Lett 48:4207CrossRefGoogle Scholar
  18. 18.
    Katritzky AR (1988) Farmaco 12:1175Google Scholar
  19. 19.
    Katritzky AR, Rachwal S, Hitchings GJ (1991) Tetrahedron 47:2683CrossRefGoogle Scholar
  20. 20.
    Katritzky AR (1992) Bull Soc Chim Belg 101:409CrossRefGoogle Scholar
  21. 21.
    Katritzky AR, Yang Z, Cundy DJ (1994) Aldrichimica Acta 27:31Google Scholar
  22. 22.
    Katritzky AR, Lan X (1994) Chem Soc Rev 363Google Scholar
  23. 23.
    Katritzky AR, Lan X, Fan WQ (1994) Synthesis 445Google Scholar
  24. 24.
    Katritzky AR, Oniciu DC (1996) Bull Soc Chim Belg 105:635Google Scholar
  25. 25.
    Carlini R, Bria E, Giannarelli D, Ferretti G, Felici A, Papaldo P, Fabi A, Nistico C, Cosimo S, Ruggeri EM, Milella M, Mottolese M, Terzoli E, Cognetti F (2005) Cancer 104:1335CrossRefGoogle Scholar
  26. 26.
    Semple G, Skinner PJ, Cherrier MC, Webb PJ, Sage CR, Tamura SY, Chen R, Richman JG, Connolly DT (2006) J Med Chem 49:1227CrossRefGoogle Scholar
  27. 27.
    Dipesa AJ, Donahue KM, Dombroski MA, Elliott NC, Gabel CA, Han S, Hynes TR, LeMotte PK, Mansour MN, Marr ES, Letavic MA, Pandit J, Ripin DB, Sweeney FJ, Tan D, Tao Y (2005) J Med Chem 48:5728CrossRefGoogle Scholar
  28. 28.
    Wu CY, King KY, Fang JM, Wu YT, Ho MY, Liao CL, Shie J, Liang PH, Wong CH (2006) Chem Biol 13:261CrossRefGoogle Scholar
  29. 29.
    Katritzky AR, Jiang J, Urogdi L (1989) Tetrahedron Lett 25:3303CrossRefGoogle Scholar
  30. 30.
    Wender PA, Touami SM, Alayrac C, Philipp UC (1996) J Am Chem Soc 118:6522CrossRefGoogle Scholar
  31. 31.
    Katritzky AR, Jiang J, Urogdi L (1990) Synthesis 565Google Scholar
  32. 32.
    Katritzky AR, Yao J, Bao W, Qi M, Steel PJ (1999) J Org Chem 64:346CrossRefGoogle Scholar
  33. 33.
    Katritzky AR, Wang M, Wilkerson CR, Yang H (2003) J Org Chem 68:9105CrossRefGoogle Scholar
  34. 34.
    Stapley EO, Hendlin D, Jackson M, Miller AK, Hernandez S, Mata JM (1971) J Antibiot 24:42Google Scholar
  35. 35.
    Miller TW, Tristram EW, Wolf FJ (1971) J Antibiot 24:48Google Scholar
  36. 36.
    Molinski TF, Ireland CM (1998) J Org Chem 53:2103CrossRefGoogle Scholar
  37. 37.
    Salomon CE, Williams DH, Faulkner DJ (1995) J Nat Prod 58:1463CrossRefGoogle Scholar
  38. 38.
    Katritzky AR, Jiang J (1995) J Org Chem 60:7597CrossRefGoogle Scholar
  39. 39.
    Chincholkar PM, Puranik VG, Deshmukh ARS (2007) Tetrahedron 63:9179CrossRefGoogle Scholar
  40. 40.
    Kale RR, Singh A, Prasad V, Tiwari VK (2010) Med Chem Res 1:107Google Scholar
  41. 41.
    Katritzky AR, Koditz J, Lang H (1994) Tetrahedron 50:12571CrossRefGoogle Scholar
  42. 42.
    Katritzky AR, Feng D, Qi M (1998) Tetrahedron Lett 39:6835CrossRefGoogle Scholar
  43. 43.
    Katritzky AR, Wang X, Denisenko A (2001) J Org Chem 66:2850CrossRefGoogle Scholar
  44. 44.
    Katritzky AR, Yao J, Yang B (1999) J Org Chem 64:6066CrossRefGoogle Scholar
  45. 45.
    Katritzky AR, Cui X, Long Q, Mehta S, Steel PJ (2000) Arkivoc iv:471Google Scholar
  46. 46.
    Katritzky AR, Zhu L, Lang H, Denisko O, Wang Z (1995) Tetrahedron 51:13271CrossRefGoogle Scholar
  47. 47.
    Katritzky AR, Wu H, Xie L, Rachwal S, Rachwal B, Jiang J, Zhang G, Lang H (1995) Synthesis 1315Google Scholar
  48. 48.
    Katritzky AR, Chang HX, Verin SV (1995) Tetrahedron Lett 36:343CrossRefGoogle Scholar
  49. 49.
    Yavari I, Alizadeh A, Abbasinejad MA (2002) Tetrahedron Lett 43:9449CrossRefGoogle Scholar
  50. 50.
    Katritzky AR, Kirichenko K, Hur D, Zhao X, Ji Y, Steel PJ (2004) Arkivoc vi:27Google Scholar
  51. 51.
    Katritzky AR, Ji Y, Fang Y, Prakash I (2001) J Org Chem 66:5613CrossRefGoogle Scholar
  52. 52.
    Katritzky AR, Hur D, Kirichenko K, Ji Y, Steel PJ (2004) Arkivoc ii:109Google Scholar
  53. 53.
    Katritzky AR, Wang X, Maimait R (2000) J Org Chem 65:8077CrossRefGoogle Scholar
  54. 54.
    Sasmal PK, Sridhar S, Iqbal J (2006) Tetrahedron Lett 47:8661CrossRefGoogle Scholar
  55. 55.
    Katritzky AR, Cai C, Suzuki K, Singh SK (2004) J Org Chem 69:811CrossRefGoogle Scholar
  56. 56.
    Katritzky AR, Qiu G, Yang B (1997) J Org Chem 62:8210CrossRefGoogle Scholar
  57. 57.
    Katritzky AR, Luo Z, Fang Y, Steel PJ (2001) J Org Chem 66:2858CrossRefGoogle Scholar
  58. 58.
    Katritzky AR, Wang M, Zhang S, Voronkov MV (2001) J Org Chem 66:6787CrossRefGoogle Scholar
  59. 59.
    Gergely M, Makara YM, Laura M (2002) Org Lett 4:1751CrossRefGoogle Scholar
  60. 60.
    Larsen SD, DiPaolo BA (2001) Org Lett 3:3341CrossRefGoogle Scholar
  61. 61.
    Katritzky AR, Qi M, Feng D, Zhang G, Griffith MZ, Watson K (1999) Org Lett 1:1189CrossRefGoogle Scholar
  62. 62.
    Katritzky AR, Shestopalov AA, Suzuki K (2005) Arkivoc vii:36Google Scholar
  63. 63.
    Zabrocki J, Dunbar JB Jr, Marshall KW, Toth MV, Marshall GR (1992) J Org Chem 57:202CrossRefGoogle Scholar
  64. 64.
    LeTiran A, Stables JP, Kohn H (2001) Bioorg Med Chem 9:2693CrossRefGoogle Scholar
  65. 65.
    Xiao J, Zhang X, Wang D, Yuan C (1999) J Fluorine Chem 99:83CrossRefGoogle Scholar
  66. 66.
    Hegarty AF, Tynan NM, Fergus S (2002) J Chem Soc Perkin Trans 2:1328Google Scholar
  67. 67.
    Thomas EW (1993) Synthesis 767Google Scholar
  68. 68.
    Lehnhoff S, Ugi I (1995) Heterocycles 40:801CrossRefGoogle Scholar
  69. 69.
    Artamonova TV, Zhivich AB, Dubinskii MY, Koldobskii GI (1996) Synthesis 1428Google Scholar
  70. 70.
    Tokes AL, Litkei G (1993) Synth Commun 23:895CrossRefGoogle Scholar
  71. 71.
    Suzuki H, Hwang YS, Nakaya C, Matano Y (1993) Synthesis 1218Google Scholar
  72. 72.
    El-Ahl AS, Elmorsy SS, Soliman H, Amer FA (1995) Tetrahedron Lett 36:7337CrossRefGoogle Scholar
  73. 73.
    Nishiyama K, Watanabe A (1984) Chem Lett 455Google Scholar
  74. 74.
    Magnus P, Taylor GM (1991) J Chem Soc Perkin Trans 1:2657CrossRefGoogle Scholar
  75. 75.
    Butler RN, O’Donoghue DA (1983) J Chem Res Synop 18Google Scholar
  76. 76.
    Ueyama N, Yanagisawa T, Kawai T, Sonegawa M, Baba H, Mochizuki S, Kosakai K, Tomiyama T (1994) Chem Pharm Bull 42:1841Google Scholar
  77. 77.
    Demko ZP, Sharpless KB (2002) Angew Chem Int Ed 41:2113CrossRefGoogle Scholar
  78. 78.
    Demko ZP, Sharpless KB (2002) Angew Chem Int Ed 41:2110CrossRefGoogle Scholar
  79. 79.
    Couty F, Durrat F, Prim D (2004) Tetrahedron Lett 45:3725CrossRefGoogle Scholar
  80. 80.
    Amer MIK, Booth BL (1993) J Chem Res Synop 4Google Scholar
  81. 81.
    Duncia JV, Pierce ME, Santella JB III (1991) J Org Chem 56:2395CrossRefGoogle Scholar
  82. 82.
    Deady LW, Devine SM (2004) J Heterocycl Chem 41:549CrossRefGoogle Scholar
  83. 83.
    Katritzky AR, Cai C, Meher NK (2007) Synthesis 8:1204Google Scholar
  84. 84.
    Katritzky AR, Suzuki K, Singh SK, He HY (2003) J Org Chem 68:5720CrossRefGoogle Scholar
  85. 85.
    Katritzky AR, Shobana N, Pernak J, Afridi AS, Fan WQ (1992) Tetrahedron 48:7817CrossRefGoogle Scholar
  86. 86.
    Katritzky AR, Singh SK, Bobrov S (2004) J Org Chem 69:9313CrossRefGoogle Scholar
  87. 87.
    Katritzky AR, Tymoshenko DO, Monteux D, Vvedensky V, Nikonov G, Cooper CB, Deshpande M (2000) J Org Chem 65:8059CrossRefGoogle Scholar
  88. 88.
    Katritzky AR, Xu YJ, Hongbin T (2003) J Org Chem 68:4935CrossRefGoogle Scholar
  89. 89.
    Katritzky AR, Qiu G, He HY, Yang B (2000) J Org Chem 65:3683CrossRefGoogle Scholar
  90. 90.
    Katritzky AR, Qiu G, Yang B, Steel PJ (1998) J Org Chem 63:6699CrossRefGoogle Scholar
  91. 91.
    Katritzky AR, Qiu G (2001) J Org Chem 66:2862CrossRefGoogle Scholar
  92. 92.
    Loughlin WA (1998) Aust J Chem 51:875CrossRefGoogle Scholar
  93. 93.
    Balkenhohl F, Von dem Bussche-Hünnefeld C, Lansky A, Zechel C (1996) Angew Chem Int Ed 35:2289Google Scholar
  94. 94.
    Nefzi A, Ostresh JM, Houghten RA (1997) Chem Rev 97:449CrossRefGoogle Scholar
  95. 95.
    Wang Y, Wilson SR (1997) Tetrahedron Lett 38:4021CrossRefGoogle Scholar
  96. 96.
    Chen C, McDonald IA, Munoz B (1998) Tetrahedron Lett 39:217CrossRefGoogle Scholar
  97. 97.
    Chen C, Munoz B (1998) Tetrahedron Lett 39:6781CrossRefGoogle Scholar
  98. 98.
    Far AR, Tidwell TT (1998) J Org Chem 63:8636CrossRefGoogle Scholar
  99. 99.
    Grosche P, Höltzel A, Walk TB, Trautwein AW, Jung G (1999) Synthesis 1961Google Scholar
  100. 100.
    Katritzky AR, Chassaing C, Barrow SJ, Zhang Z, Vvedensky V, Forood B (2002) J Comb Chem 4:249CrossRefGoogle Scholar
  101. 101.
    Katritzky AR, Rachwal S, Rachwal B (1987) J Chem Soc Perkin Trans 1:791CrossRefGoogle Scholar
  102. 102.
    Katritzky AR, Rachwal S, Wu J (1990) Can J Chem 68:446CrossRefGoogle Scholar
  103. 103.
    Katritzky AR, Luo Z, Cui XL (1999) J Org Chem 64:3328CrossRefGoogle Scholar
  104. 104.
    Katritzky AR, Xu YJ, Jain R (2002) J Org Chem 67:8234CrossRefGoogle Scholar
  105. 105.
    Degl’Innocenti A, Capperucci A, Oniciu DC, Katritzky AR (2000) J Org Chem 65:9206CrossRefGoogle Scholar
  106. 106.
    Mhaske SB, Argade NP (2006) Tetrahedron 62:9787CrossRefGoogle Scholar
  107. 107.
    Kobayashi S, Ueno M, Suzuki R, Ishitani H (1999) Tetrahedron Lett 40:2175CrossRefGoogle Scholar
  108. 108.
    Katritzky AR, Ledoux S, Witek RM, Nair SK (2004) J Org Chem 69:2976CrossRefGoogle Scholar
  109. 109.
    Tiwari VK, Singh DD, Hussain HA, Mishra BB, Singh A (2008) Monatsh Chem 139:43CrossRefGoogle Scholar
  110. 110.
    Tiwari VK, Hussain HA, Mishra BB, Singh DD, Tripathi V (2007) Med Chem Res 15:325Google Scholar
  111. 111.
    Tiwari VK, Kale RR, Mishra BB, Singh A (2008) Arkivoc xiv:27Google Scholar
  112. 112.
    Tiwari VK, Singh A, Hussain HA, Mishra BB, Tripathi V (2007) Monatsh Chem 138:1257CrossRefGoogle Scholar
  113. 113.
    Singh A, Kale RR, Tiwari VK (2009) Trends Carbohydr Res 1:80Google Scholar
  114. 114.
    Tewari N, Mishra RC, Tiwari VK, Tripathi RP (2002) Synlett 11:1779Google Scholar
  115. 115.
    Katritzky AR, Rogovoy B, Klein C, Insuasty H, Vedensky V, Insuasty B (2001) J Org Chem 66:2854CrossRefGoogle Scholar
  116. 116.
    Katritzky AR, Singh SK, Akhmedova R, Cai C, Bobrov S (2007) Arkivoc vi:6Google Scholar
  117. 117.
    Katritzky AR, Rogers JW, Witek RM, Nair SK (2004) Arkivoc viii:52Google Scholar
  118. 118.
    Abonia R, Rengifo E, Quiroga J, Insuasty B, Cobob V, Noguerasb M (2004) Tetrahedron 60:8839CrossRefGoogle Scholar
  119. 119.
    Katritzky AR, Jain R, Xu YJ, Steel PJ (2002) J Org Chem 67:8220CrossRefGoogle Scholar
  120. 120.
    Khalaj A, Pirali M, Matloubi H, Dowlatabadi R (2001) Monatsh Chem 132:747Google Scholar
  121. 121.
    Katritzky AR, Xu YJ, He HY, Mehta S (2001) J Org Chem 66:5590CrossRefGoogle Scholar
  122. 122.
    Katritzky AR, Xie L (1995) J Org Chem 60:3707CrossRefGoogle Scholar
  123. 123.
    Katritzky AR, Mehta S, Ying He H (2001) J Org Chem 66:148CrossRefGoogle Scholar
  124. 124.
    Katritzky AR, Yannakopoulou K (1989) Heterocycles 28:1121CrossRefGoogle Scholar
  125. 125.
    Katritzky AR, Yang Z, Lam JN, Cundy DJ (1993) Heterocycles 36:1367CrossRefGoogle Scholar
  126. 126.
    Katritzky AR, Li J, Stevens CV (1995) J Org Chem 60:3401CrossRefGoogle Scholar
  127. 127.
    Katritzky AR, Yang B, Jiang J, Steel PJ (1995) J Org Chem 60:246CrossRefGoogle Scholar
  128. 128.
    Katritzky AR, Zhang G, Jiang J, Steel PJ (1995) J Org Chem 60:7625CrossRefGoogle Scholar
  129. 129.
    Nakamura I, Nemoto T, Shiraiwa N, Terada M (2009) Org Lett 11:5CrossRefGoogle Scholar
  130. 130.
    Katritzky AR, Huang TB, Denisko OV, Steel PJ (2002) J Org Chem 67:3118CrossRefGoogle Scholar
  131. 131.
    Booker Milburn KI, Wood PM, Dainty RF, Urquhart MW, White AJ, Lyon HJ, Charmant JPH (2002) Org Lett 4:1487CrossRefGoogle Scholar
  132. 132.
    Knight DW, Little PB (2001) J Chem Soc Perkin Trans 1:1771CrossRefGoogle Scholar
  133. 133.
    Katritzky AR, Bobrov S, Tao H, Kirichenko K (2005) Tetrahedron 61:3305CrossRefGoogle Scholar
  134. 134.
    Katritzky AR, Bobrov S, Kirichenko K, Ji Y, Steel PJ (2003) J Org Chem 68:5713CrossRefGoogle Scholar
  135. 135.
    Verma AK, Kesharwani T, Singh J, Tandon V, Larock RC (2009) Angew Chem Int Ed 48:1138CrossRefGoogle Scholar
  136. 136.
    Verma AK, Singh J, Larock RC (2009) Tetrahedron 65:8434CrossRefGoogle Scholar

Copyright information

© Springer-Verlag 2010

Authors and Affiliations

  • Raju R. Kale
    • 1
  • Virendra Prasad
    • 1
  • Prabhu P. Mohapatra
    • 2
  • Vinod K. Tiwari
    • 1
  1. 1.Department of Chemistry, Centre of Advanced StudyBanaras Hindu UniversityVaranasiIndia
  2. 2.Reviva Pharmaceuticals Inc.San JoseUSA

Personalised recommendations