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Five-Membered Heterocycles with More than Two Heteroatoms

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Abstract

Five-membered heterocycles with more than two heteroatoms are considered to be derived from pyrrole, furan and thiophene by the replacement of methine groups (-CH=) by pyridine-type nitrogen (-N=) atoms from the different positions and are named as (Fig. 1)1:

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References

  1. A. R. Katritzky and J. M. Lagowski in A. R. Katritzky and C. W. Rees (Eds.), Comprehensive Heterocyclic Chemistry Vol. 5, Pergamon Press, Oxford, 1984, pp. 1.

    Chapter  Google Scholar 

  2. A. R. Katritzky and J. M. Lagowski in A. R. Katritzky and C. W. Rees (Eds.), Comprehensive Heterocyclic Chemistry Vol. 5, Pergamon Press, Oxford, 1984, pp. 39.

    Chapter  Google Scholar 

  3. M. R. Grimmett in D. H. R. Barton and W. D. Fis (Eds.), Comprehensive Organic Chemistry Vol. 4, Pergamon Press, Oxford, 1979, pp. 357.

    Google Scholar 

  4. J. A. Zoltewicz and L. W. Deady, Adv. Heterocycl. Chem. 22, 71 (1978).

    Article  CAS  Google Scholar 

  5. K. Schofield, M. R. Grimmett and B. R. T. Keena, Heteroaromatic Nitrogen Compounds — The Azoles, Cambridge University Press, Cambridge, 1976.

    Google Scholar 

  6. T. L. Gilchrist and G. E. Gymer, Adv. Heterocycl. Chem. 16, 33 (1974)

    Article  CAS  Google Scholar 

  7. A. Albert and P.J. Taylor, J. Chem. Soc. Perkin Trans. 1, 2789 (1989).

    Google Scholar 

  8. H. Wamhoff in A. R. Katritzky and C.W. Rees (Eds.), Comprehensive Heterocyclic Chemistry Vol. 5, Pergamon Press, Oxford, 1984, pp. 669

    Google Scholar 

  9. M. Begtrup and P. Larsen, Acta Chem. Scand. 44, 1050 (1990).

    Article  CAS  Google Scholar 

  10. H. Suschitzky and O. Meth—Cohn, Heterocyclic Chemistry Vol. 1, The Royal Society of Chemistry, London, 1980, pp. 220.

    Book  Google Scholar 

  11. K.T. Finley, Chem. Heterocycl. Compd. 39, 1 (1980).

    Article  Google Scholar 

  12. S. Hauptmann, H. Wilde and K. Moser, J. Prakt. Chem. 313, 882 (1971)

    Article  CAS  Google Scholar 

  13. J. Sieler, H. Wilde and S. Hauptmann, Z. Chem. 11, 179 (1971).

    Article  CAS  Google Scholar 

  14. R. N. Butler, A. B. Hanahoe and W.B. King, J. Chem. Soc. Perkin Trans. 1, 881 (1978).

    Article  Google Scholar 

  15. T. L. Gilchrist, G. E. Gymer and C. W. Rees, J. Chem. Soc. Perkin Trans. 1, 555 (1973).

    Article  Google Scholar 

  16. T. Sheradsky in The Chemistry of the Azido Group, Wiley-Interscience, New York, 1971, pp. 331.

    Google Scholar 

  17. L. Birkofer and O. Stuhl, Top. Curr. Chem. 88, 33 (1980).

    Article  CAS  Google Scholar 

  18. T. L. Gilchrist, G. E. Gymer and C. W. Rees, Chem. Commun. 1519 (1971).

    Google Scholar 

  19. R. Selvarajan and J. H. Boyer, J. Heterocycl. Chem. 9, 87 (1972).

    Article  CAS  Google Scholar 

  20. D. J. Brown in B. S. Thyagarajan (Ed.), Mechanisms of Molecular Migrations Vol. 1, Wiley-Interscience, New York, 1968, pp. 209.

    Google Scholar 

  21. P. A. S. Smith, L. O. Krbechek and W. Resemann, J. Am. Chem. Soc. 86, 2025 (1964)

    Article  CAS  Google Scholar 

  22. P. A. S. Smith, G. J. W. Breen, M. K. Hajek and D. V. C. Awang, J. Org. Chem. 35, 2215 (1970).

    Article  CAS  Google Scholar 

  23. K. T. Potts, Chem. Rev. 61, 87 (1961).

    Article  Google Scholar 

  24. C. Temple, Jr., Chem. Heterocycl. Compd. 37, 1 (1981).

    Article  Google Scholar 

  25. J. B. Polya in A. R. Katritzky and C. W. Rees (Eds.), Comprehensive Heterocyclic Chemistry Vol. 5, Pergamon Press, Oxford, 1984, pp. 733.

    Google Scholar 

  26. P. Goldstein, J. Ladell and C. Abowitz, Acta Crystallogr. Part B, 25, 135 (1969).

    Article  CAS  Google Scholar 

  27. M. J. S. Dewar and T. Morita, J. Am. Chem. Soc. 91, 796 (1969).

    Article  CAS  Google Scholar 

  28. A. Bernardini, P. Viallefont, J. Daunis, M. L. Roumestant and A. B. Soulami, Bull. Soc. Chim. France, 647 (1975).

    Google Scholar 

  29. J. P. Gasparini, R. Gassend, J. C. Maire and J. Elguero, J. Organomet. Chem. 188, 141 (1980).

    Google Scholar 

  30. R. A. Olofson and R. V. Kendall, J. Org. Chem. 35, 2246 (1970).

    Article  CAS  Google Scholar 

  31. C. L. Habraken and P. Cohen-ernandes, J. Chem. Soc. Chem. Commun. 37 (1972).

    Google Scholar 

  32. H. -J. Timpe, Adv. Heterocycl. Chem. 17, 213 (1974).

    Article  Google Scholar 

  33. R. L. Jones and C. W. Rees, J. Chem. Soc. (C), 2251 (1969).

    Google Scholar 

  34. K. Sakai and J. P. Anselme, Tetrahedron Lett. 3851 (1970).

    Google Scholar 

  35. W. D. 011is and C. A. Ramsden, Adv. Heterocycl. Chem. 19, 1 (1976).

    Article  CAS  Google Scholar 

  36. R. N. Butler, Adv. Heterocycl. Chem. 21, 323 (1977).

    Article  Google Scholar 

  37. R. N. Butler in A. R. Katritzky and C. W. Rees (Eds.), Comprehensive Heterocyclic Chemistry Vol. 5, Pergamon Press, Oxford 1984, pp. 791.

    Google Scholar 

  38. K. Potts in H. Suschitzky and E. F. V. Scriven (Eds.), Progress in Heterocyclic Chemistry Vol. 1, Pergamon Press, Oxford, 1989, pp. 143

    Google Scholar 

  39. S. A. Lang, Jr. and C. B. Zieglar, Jr. Vol. 2, 1990, pp. 102

    CAS  Google Scholar 

  40. S. A. Lang, Jr. and V. J. Lee, Vol. 3, 1991, pp. 124; Vol. 4, 1992, pp. 107; Vol. 5,1993, pp. 143; Vol. 6, 1994, pp. 147.

    CAS  Google Scholar 

  41. J. Kaczmarek, H. Smagowski and Z. Grzonka, J. Chem. Soc. Perkin Trans. 2, 1670 (1979)

    Google Scholar 

  42. J. Ciarkowski, J. Kaczmarek and Z. Grzonka, Org. Magn. Reson. 12, 631 (1979).

    Article  CAS  Google Scholar 

  43. M. Tisler, Synthesis, 123 (1973).

    Google Scholar 

  44. L. A. Lee, R. Evans and J. W. Wheeler, J. Org. Chem. 37, 343 (1972).

    Article  CAS  Google Scholar 

  45. A. Hassner, Acc. Chem. Res. 4, 10 (1971)

    Article  Google Scholar 

  46. H. Singh, K. K. Bhutani and L. R. Gupta, J. Chem. Soc. Perkin Trans. 1, 1210 (1976)

    Article  Google Scholar 

  47. R. N. Butler and D. A. O’Donoghue, J. Chem. Res. (S), 18 (1983).

    Google Scholar 

  48. R. M. Herbst, J. Org. Chem. 26, 2372 (1961).

    Article  Google Scholar 

  49. O. Subba Rao and W. Lwowski, J. Heterocycl. Chem. 17, 187 (1980).

    Article  Google Scholar 

  50. R. Huisgen, Angew. Chem. Int. Ed. Engl. 19, 947 (1980).

    Article  Google Scholar 

  51. A. Padwa, S. Nahun and E. Sato, J. Org. Chem. 43, 1664 (1978)

    Article  CAS  Google Scholar 

  52. A. Könnecke, P. Lepom and E. Lippmann, Z. Chem. 18, 214 (1978).

    Article  Google Scholar 

  53. L. B. Clapp, Adv. Heterocycl. Chem. 20, 65 (1976).

    Article  Google Scholar 

  54. L. B. Clapp in A. R. Katritzky and C. W. Rees (Eds.), Comprehensive Heterocyclic Chemistry Vol. 6, Pergamon Press, Oxford, 1984, pp. 365.

    Google Scholar 

  55. N. S. Ooi and D. A. Wilson, J. Chem. Soc. Perkin Trans. 2, 1792 (1980).

    Google Scholar 

  56. M. J. Dimsdale, J. Heterocycl. Chem. 18, 37 (1981).

    Article  Google Scholar 

  57. H. L. Yale and E. R. Spitzmiller, J. Heterocycl. Chem. 15, 1373 (1978).

    Article  CAS  Google Scholar 

  58. K. L. Stuart, Heterocycles, 3, 651 (1975)

    Article  Google Scholar 

  59. W. Silva, Heterocycles, 22, 1571 (1984).

    Article  Google Scholar 

  60. A. Gasco and A. J. Boulton, Adv. Heterocycl. Chem. 29, 251 (1981)

    Article  CAS  Google Scholar 

  61. A. J. Boulton and P. B. Ghosh, Adv. Heterocycl. Chem. 10, 1 (1969).

    Article  CAS  Google Scholar 

  62. R. M. Paton in A. R. Katritzky and C. W. Rees (Eds.), Comprehensive Heterocyclic Chemistry Vol. 6, Pergamon Press, Oxford, 1984, pp. 393.

    Google Scholar 

  63. M. Ruccia, N. Vivona and D. Spinelli, Adv. Heterocycl. Chem. 29, 141 (1981).

    Article  CAS  Google Scholar 

  64. S. K. Talapatra, P. Chaudhuri and B. Talapatra, Heterocycles, 14, 1279 (1980)

    Article  CAS  Google Scholar 

  65. W. Silva and A. Thomas, Heterocycles 23, 399 (1985).

    Article  Google Scholar 

  66. I. P. Bachkovskii, A. P. Mikhailovski and V. A. Chuiguk, Ukr. Khim. Zh. 46, 637 (1980)

    CAS  Google Scholar 

  67. I. P. Bachkovskii, A. P. Mikhailovski and V. A. Chuiguk, Chem. Abstr. 93, 168–22 (1980).

    Google Scholar 

  68. A. Hetzheim and K. Möckel, Adv. Heterocycl. Chem. 7, 183 (1966).

    Article  CAS  Google Scholar 

  69. L. C. Behr, Chem. Heterocycl. Compd. 17, 263 (1962)

    Article  Google Scholar 

  70. E. P. Nesynov and A. P. Grekov, Russ. Chem. Rev. 33, 508 (1964).

    Article  Google Scholar 

  71. J. Hill in A. R. Katritzky and C. W. Rees (Eds.), Comprehensive Heterocyclic Chemistry Vol. 6, Pergamon Press, Oxford, 1984, pp. 427.

    Google Scholar 

  72. M. Golfier and R. Milcent, Tetrahedron Lett. 3871 (1974).

    Google Scholar 

  73. K. 0e, M. Tashiro and O. Tsuge, Bull. Chem. Soc. Japan 50, 3281 (1977).

    Article  CAS  Google Scholar 

  74. M. M. Campbell in D. H. R. Barton and W. D. Ollis (Eds.), Comprehensive Organic Chemistry Vol. 4, Pergamon Press, Oxford, 1979, pp. 1033.

    Google Scholar 

  75. E. W. Thomas in A. R. Katritzky and C. W. Rees. (Eds.), Comprehensive Heterocyclic Chemistry Vol. 6, Pergamon Press, Oxford, 1984, pp. 447.

    Google Scholar 

  76. R. Tanaka in H. Suschitzky and E. F. V. Scriven (Eds.), Progress in Heterocyclic Chemistry Vol. 6 Pergamon Press, Oxford, 1994, pp. 163 and references therein

    Google Scholar 

  77. M. Fujta, T. Kobori, T. Hiyame and K. Kondo, Heterocycles, 36, 33 (1993).

    Article  Google Scholar 

  78. N. P. Peet and S. Sunder, J. Heterocycl. Chem. 12, 1191 (1975).

    Article  CAS  Google Scholar 

  79. F. Bellesia, R. Grandi, U. M. Pagnoni and R. Trave, Gazz, Chim. Ital. 111, 289 (1981).

    CAS  Google Scholar 

  80. S. Auricchio, S. Bruckner, L. M. Giunchi, V. A. Kozinsky and O. V. Zelenskaja, J. Heterocycl. Chem. 17, 1217 (1980).

    Article  CAS  Google Scholar 

  81. K. Masuda, J. Adachi, H. Nate, H. Takahata and K. Nomura, J. Chem. Soc. Perkin Trans. 1, 1591 (1981)

    Article  Google Scholar 

  82. K. Masuda, J. Adachi, H. Moria and K. Nomura, Chem. Pharm. Bull. 29, 1743 (1981).

    Article  CAS  Google Scholar 

  83. B. Modarai, M.H. Ghanderhari, H. Massoumi, A. Shafiee, I. Lalezari and A. Badali, J. Heterocycl. Chem. 11, 343 (1974).

    Article  CAS  Google Scholar 

  84. G. Trickes, H. P. Braun and H. Meir, Liebigs Ann. Chem. 1347 (1977)

    Google Scholar 

  85. W. Winter, U. Plücken and H. Meier, Z. Naturforsch. Teil B 33, 316 (1978).

    Google Scholar 

  86. J. Font, M. Tones, H. E. Gunning and O. P. Strausz, J. Org. Chem. 43, 2487 (1978).

    Article  CAS  Google Scholar 

  87. A. Krantz and J. Laureni, J. Am. Chem. Soc. 99, 4842 (1977).

    Article  CAS  Google Scholar 

  88. C. Wentrup, Adv. Heterocycl. Chem. 28, 231 (1981).

    Article  CAS  Google Scholar 

  89. F. Kurzer, Adv. Heterocycl. Chem. 5, 119 (1965).

    Article  CAS  Google Scholar 

  90. F. Kurzer, Org. Compd. Sulphur, Selenium, Tellurium 4, 422 (1977).

    Google Scholar 

  91. F. Kurzer, Adv. Heterocycl. Chem. 32, 285 (1982).

    Article  CAS  Google Scholar 

  92. L. E. Franz and O. P. Dhingra in A. R. Katritzky and C. W. Rees (Eds.), Comprehensive Heterocyclic Chemistry Vol. 6, Pergamon Press, Oxford, 1984, pp. 463.

    Chapter  Google Scholar 

  93. M. Ruccia, N. Vivona and G. Cusmano, J. Chem. Soc. Chem. Commun. 358 (1974)

    Google Scholar 

  94. N. Vivona, G. Cusmano and G. Macaluso J. Chem. Soc. Perkin Trans. 1, 1616 (1977).

    Article  Google Scholar 

  95. T. J. Curphey and K.S. Prasad, J. Org. Chem. 37, 2259 (1972).

    Article  CAS  Google Scholar 

  96. O. L. Stiefvater, Z. Naturforsch. Teil A 31, 1681 (1976).

    Google Scholar 

  97. L. M. Weinstock and P. J. Pollack, Adv. Heterocycl. Chem. 9, 107 (1968).

    Article  CAS  Google Scholar 

  98. V. G. Pesin, Russ. Chem. Rev. (Engl. Trans.) 39, 923 (1970).

    Google Scholar 

  99. L. M. Weinstock and I. Shinkai in A. R. Katritzky and C. W. Rees (Eds.), Comprehensive Heterocyclic Chemistry Vol. 6, Pergamon Press, Oxford, 1984, pp. 513.

    Chapter  Google Scholar 

  100. V. Bertini, F. Lucchesini and A. De Munno, Tetrahedron 36, 1245 (1980).

    Article  CAS  Google Scholar 

  101. R. W. Begland and D. R. Hartter, J. Org. Chem. 37, 4136 (1972).

    Article  CAS  Google Scholar 

  102. J. Rokach, P. Hamel, Y. Girard and G. Reader, J. Org. Chem. 44, 1118 (1979).

    Article  CAS  Google Scholar 

  103. K. Masuda, J. Adachi and K. Nomura, J. Chem. Soc. Perkin Trans. 1, 1033 (1981).

    Article  Google Scholar 

  104. R. G. Micetich, Can. J. Chem. 48, 2006 (1970).

    Google Scholar 

  105. J. Rokach, P. Hamel, Y. Girard and G. Reader, Tetrahedron Lett. 1281 (1979).

    Google Scholar 

  106. J. Sandstrom, Adv. Heterocycl. Chem. 9, 165 (1968).

    Article  CAS  Google Scholar 

  107. M. M. Campbell in D. H. R. Barton and W. D. 011is (Eds.), Comprehensive Organic Chemistry Vol. 4, Pergamon Press, Oxford 1979, pp. 961.

    Google Scholar 

  108. G. Komis in A. R. Katritzky and C. W. Rees (Eds.), Comprehensive Heterocyclic Chemistry Vol. 6 Pergamon Press, Oxford, 1984. pp. 545.

    Google Scholar 

  109. F. Kurzer, Org. Compd. Sulphur, Selenium, Tellurium 1, 449 (1970)

    Google Scholar 

  110. F. Kurzer, Org. Compd. Sulphur, Selenium, Tellurium 2, 725 (1973)

    Google Scholar 

  111. F. Kurzer, Org. Compd. Sulphur, Selenium, Tellurium 3, 687 (1975)

    Google Scholar 

  112. F. Kurzer, Org. Compd. Sulphur, Selenium, Tellurium 4, 431 (1977)

    Google Scholar 

  113. M. Davis, Org. Compd. Sulphur, Selenium, Tellurium 5, 440 (1979).

    Google Scholar 

  114. T. J. Kress and S. M. Costantino, J. Heterocycl. Chem. 17, 607 (1980).

    Article  CAS  Google Scholar 

  115. R. F. Lauer and G. Zenchoff, J. Heterocycl. Chem. 13, 291 (1976).

    Article  CAS  Google Scholar 

  116. H. Lund, Acta Chem. Scand. 27, 391 (1973).

    Article  CAS  Google Scholar 

  117. M. L. Schenetti, F. Taddei, L. Greci, L. Marchetti, G. Milani, G. D. Andreetti, G. Bolelli and P. Sgarabotto, J. Chem. Soc. Perkin Trans. 2, 421 (1980).

    Google Scholar 

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  1. Department of Chemistry, University of Rajasthan, 302004, Jaipur, India

    Prof. Radha Raman Gupta, Dr. Mahendra Kumar & Dr. Vandana Gupta

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Gupta, R.R., Kumar, M., Gupta, V. (1999). Five-Membered Heterocycles with More than Two Heteroatoms. In: Heterocyclic Chemistry. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-662-07757-3_5

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