Skip to main content
SpringerLink
Log in

Methods for the synthesis of 2-aminothiophenes and their reactions (review)

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

2-Aminothiophenes are readily formed as a result of various cyclization reactions. The method of preparation of derivatives of 2-aminothiophene-3-carboxylic acids and 2-amino-3-acylthiophenes from carbonyl compounds, nitriles that have an active methylene group, and sulfur is particularly simple and rich in possibilities. The aminothiophenes can be converted to other thiophene derivatives and used primarily for the preparation of condensed thiophenes such as thionaphthenes, thienopyrroles, thienothiazoles, thienoisothiazoles, thienopyrimidines, thienopyridines, and thienodiazepines.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

Literature cited

  1. H. D. Hartough, in: Thiophene and Its Derivatives, Wiley-Interscience, New York (1952).

    Google Scholar 

  2. S. Gronowitz, Advances in Heterocyclic Chemistry, Vol. 1, Academic Press, New York (1963), p. 1.

    Google Scholar 

  3. C. D. Hurd, International J. Sulphur Chem. B,4, 75 (1969).

    Google Scholar 

  4. H. Hartmann and S. Scheithauer, J. Prakt. Chem.,311, 827 (1969).

    Google Scholar 

  5. S. Gronowitz, in: Organic Compounds of Sulphur, Selenium, and Tellurium, Vol. 2, The Chemical Society, London (1973), p. 35.

    Google Scholar 

  6. S. Gronowitz, in: Organic Chemistry of Sulphur, Selenium and Tellurium, Vol. 3, The Chemical Society, London (1975), p. 400.

    Google Scholar 

  7. W. J. Middleton, V. A. Engelhardt, and B. S. Fisher, J. Am. Chem. Soc.,80, 2822 (1958).

    Google Scholar 

  8. H. Hartmann and R. Mayer, Z. Chem.,6, 28 (1966).

    Google Scholar 

  9. I. Meijer and L. Brandsma, Rec. Trav. Chim.,92, 1331 (1973).

    Google Scholar 

  10. R. Gompper and E. Kutter, Angew. Chem.,74, 251 (1962).

    Google Scholar 

  11. R. Laliberte and G. Medawar, Can. J. Chem.,49, 1372 (1971).

    Google Scholar 

  12. S. Rajappa and B. G. Advani, Tetrehedron Lett., No. 50, 5067 (1969).

    Google Scholar 

  13. S. Rajappa and B. G. Advani, Indian J. Chem.,9, 759, 761 (1971).

    Google Scholar 

  14. J. P. Chupp, J. Heterocycl. Chem.,7, 285 (1970).

    Google Scholar 

  15. H. Behringer and K. Falkenberg, Ber.,99, 3309 (1966).

    Google Scholar 

  16. G. W. Stacy and D. L. Eck, Tetrahedron Lett., No. 51, 5201 (1967).

    Google Scholar 

  17. G. W. Stacy and D. L. Eck, J. Heterocycl. Chem.,6, 147 (1969).

    Google Scholar 

  18. K. Gewald, Angew. Chem.,73, 114 (1961).

    Google Scholar 

  19. K. Gewald, Ber.,98, 3571 (1965).

    Google Scholar 

  20. K. Gewald, Z. Chem.,2, 302 (1961).

    Google Scholar 

  21. K. Gewald, H. Böttcher, and E. Schinke, Ber.,99, 94 (1966).

    Google Scholar 

  22. R. Mayer and K. Gewald, Angew. Chem.,79, 298 (1967).

    Google Scholar 

  23. V. I. Shvedov and A. N. Grinev, Khim. Geterotsikl. Soedin., No. 4, 515 (1966).

    Google Scholar 

  24. V. I. Shvedov, A. N. Grinev, and V. K. Ryzhkova, Khim. Geterotsikl. Soedin., No. 2, 239 (1967).

    Google Scholar 

  25. M. Nakanishi, T. Tahara, and H. Imamura, Japanese Patent No. 712103 [sic]; Chem. Abstr.,75, 129788 (1971).

    Google Scholar 

  26. E. F. Elslager, P. Jacob, and L. M. Wertel, J. Heterocyclic Chem.,9, 975 (1972).

    Google Scholar 

  27. A. Rossowski, K. K. N. Chen, and M. Lin, J. Med. Chem.,16, 191 (1973).

    Google Scholar 

  28. M. Nakanishi, T. Tahara, K. Araki, M. Shiroki, T. Tsungari, and Y. Takigawa, J. Med. Chem.,16, 214 (1973).

    Google Scholar 

  29. F. J. Tinney, J. P. Sanchez, and J. A. Nogas, J. Med. Chem.,17, 624 (1974).

    Google Scholar 

  30. L. G. Sharanina and S. N. Baranov, Khim. Geterotsikl. Soedin., No. 2, 196 (1974).

    Google Scholar 

  31. D. B. Baird, A. T. Costeller, R. B. Fishwick, R. D. McClelland, and P. Smith, British Patent No. 1394366 (1974); Chem. Abstr.,83, 114196 (1975).

    Google Scholar 

  32. R. F. Koebel, L. L. Needham, and C. D. Blanton, J. Med. Chem.,18, 192 (1975).

    Google Scholar 

  33. F. Asinger, W. Leuchtenberger, and H. Offermanna, Chemiker-Ztg.,98, 610 (1974).

    Google Scholar 

  34. K. Gewald, M. Hentschel, H. Böttcher, and E. Schinke, Unpublished Data.

  35. V. I. Shvedov and A. N. Grinev, Zh. Org. Khim.,1, 2228 (1965).

    Google Scholar 

  36. Yu. A. Sharanin and L. G. Sharanina, Khim. Geterotsikl. Soedin., No. 10, 1432 (1974).

    Google Scholar 

  37. R. Matusch and K. Hartke, Ber.,105, 2594 (1972).

    Google Scholar 

  38. M. Hentschel, Dissertation, TU Dresden (1974).

  39. K. Gewald and E. Schinke, Ber.,99, 2712 (1966).

    Google Scholar 

  40. E. C. Taylor and C. D. McKillop, in: Advances in Organic Chemistry, Vol. 7, Wiley-Interscience, New York (1970).

    Google Scholar 

  41. H. Shäfer and K. Gewald, J. Prakt. Chem.,316, 684 (1974).

    Google Scholar 

  42. K. Gewald, M. Hentschel, and R. Heikel, J. Prakt. Chem.,315, 539 (1974).

    Google Scholar 

  43. K. Gewald, M. Kleinert, B. Thiele, and J. Hentschel, J. Prakt. Chem.,314, 303 (1972).

    Google Scholar 

  44. H. Shäfer and K. Gewald, Unpublished Data.

  45. N. Kim Son, R. Pinel, and Y. Mollier, Bull. Soc. Chim. France, No. 2, 471 (1974).

    Google Scholar 

  46. N. Kim Son, R. Pinel, and Y. Mollier, Comptes Rend.,278, 197 (1972).

    Google Scholar 

  47. K. Gewald, M. Hentschel, and H. Jablokoff, J. Prakt. Chem.,317, 861 (1975).

    Google Scholar 

  48. R. Heckendorn and A. R. Gageux, Tetrahedron Lett., No. 25, 2279 (1973).

    Google Scholar 

  49. Ya. L. Gol'dfarb (Goldfarb), B. R. Fabrichnyi (Fabrichny), and K. F. Shalavina, Tetrahedron,18, 21 (1962).

    Google Scholar 

  50. E. C. Taylor and J. G. Berger, Angew. Chem.,78, 144 (1966).

    Google Scholar 

  51. E. C. Taylor and J. G. Berger, J. Org. Chem.,32, 2376 (1967).

    Google Scholar 

  52. V. I. Shvedov, I. A. Kharizomenova, and A. N. Grinev, Khim. Geterotsikl. Soedin., No. 6, 765 (1975).

    Google Scholar 

  53. K. Gewald, Z. Chem.,7, 186 (1967).

    Google Scholar 

  54. S. Rajappa, G. Advani, and R. Sreenivasan, Indian J. Chem.,12, 4 (1974).

    Google Scholar 

  55. V. I. Shvedov, I. A. Kharizomenova, and A. N. Grinev, Inventor's Certificate No. 364612 (1972); Chem. Abstr.,78, 159416 (1973).

    Google Scholar 

  56. C. T. Wie, C. Blanton DeWitt, and S. Sunder, Tetrahedron Lett., No. 44, 4605 (1968).

    Google Scholar 

  57. W. O. Foye, I. Michles, and G. M. Boyce, J. Pharm. Soc.,59, 1348 (1970).

    Google Scholar 

  58. M. Nakanishi, M. Shiroki, K. Araki, and T. Tahara, Japanese Patent No. 7301664; Chem. Abstr.,78, 159412 (1973).

    Google Scholar 

  59. M. Nakanishi, M. Shiroki, K. Araki, and T. Tahara, Japanese Patent No. 7301663; Chem. Abstr.,78, 159413 (1973).

    Google Scholar 

  60. M. Nakanishi, M. Shiroki, K. Araki, and T. Tahara, Japanese Patent No. 7312282; Chem. Abstr.,78, 136093 (1973).

    Google Scholar 

  61. M. Nakanishi, K. Araki, M. Shiroki, and T. Tahara, Japanese Patent No. 7301665; Chem. Abstr.,79, 31850 (1973).

    Google Scholar 

  62. M. Nakanishi, K. Araki, T. Tahara, and M. Shiroki, Japanese Patent No. 7301667; Chem. Abstr.,79, 31489 (1973).

    Google Scholar 

  63. M. Nakanishi, M. Shiroki, T. Tahara, and K. Araki, Japanese Patent No. 7308107; Chem. Abstr.,79, 18587 (1973).

    Google Scholar 

  64. M. Nakanishi, M. Shiroki, T. Tahara, and K. Araki, Japanese Patent Application No. 7322471; Chem. Abstr.,79, 18579 (1973).

    Google Scholar 

  65. M. Nakanishi, M. Shiroki, T. Tahara, and K. Araki, Japanese Patent Application No. 7322472; Chem. Abstr.,79, 18578 (1973).

    Google Scholar 

  66. M. Nakanishi, K. Araki, T. Tahara, and M. Shiroki, Japanese Patent Application No. 7416859; Chem. Abstr.,82, 139945 (1975).

    Google Scholar 

  67. M. Nakanishi, T. Tahara, K. Araki, and M. Shiroki, Japanese Patent Application No. 7416861; Chem. Abstr.,82, 97928 (1975).

    Google Scholar 

  68. F. Sauter and W. Deinhammer, Monatsh.,104, 1586 (1973).

    Google Scholar 

  69. D. B. Baird, A. T. Costello, B. R. Fishwick, R. D. McClelland, and P. Smith, West German Patent Application No. 2304201 (1973); Chem. Abstr.,79, 127402 (1973).

    Google Scholar 

  70. R. J. Mauer, J. G. Fisher, and M. A. Weaver, West German Patent No. 234512 (1972); Chem. Abstr.,80, 134899 (1974).

    Google Scholar 

  71. V. I. Shvedov, V. K. Ryzhkova, and A. N. Grinev, Khim. Geterotsikl. Soedin., No. 6, 1010 (1967).

    Google Scholar 

  72. M. Hentschel and K. Gewald, J. Prakt. Chem.,316, 878 (1974).

    Google Scholar 

  73. R. A. Crochet and Blanton C. DeWitt, Synthesis, No. 8, 556 (1974).

    Google Scholar 

  74. F. Sauter and P. Stanetty, Monatsh.,106, 1111 (1975).

    Google Scholar 

  75. M. Nakanishi, M. Shiroki, T. Tahara, and K. Araki, Japanese Patent No. 7332877; Chem. Abstr.,79, 31893 (1973).

    Google Scholar 

  76. R. A. Crochet, J. T. Boatright, and C. Blanton DeWitt, J. Heterocycl. Chem.,11, 143 (1974).

    Google Scholar 

  77. M. Wierzbicki and D. Cagniant, Bull. Soc. Chim., France, No. 5, 1786 (1975).

    Google Scholar 

  78. V. I. Shvedov, V. K. Ryzhkova, and A. N. Grinev, Khim. Geterotsikl. Soedin., No. 3, 450 (1967).

    Google Scholar 

  79. M. Hentschel, J. Morgenstern, and K. Gewald, East German Patent No. 102397 (1973).

  80. H. Hartmann, J. Prakt. Chem.,364, 50 (1967).

    Google Scholar 

  81. H. Hartmann and S. Scheithauer, J. Prakt. Chem.,311, 827 (1969).

    Google Scholar 

  82. B. Bartho, J. Faust, and R. Mayer, Z. Chem.,15, 440 (1975).

    Google Scholar 

  83. V. I. Shvedov, I. A. Kharizomenova, and A. N. Grinev, Khim. Geterotsikl. Soedin., No. 1, 58 (1974).

    Google Scholar 

  84. V. I. Shvedov, I. A. Kharizomenova, and A. N. Grinev, Khim. Geterotsikl. Soedin., No. 91204 (1974).

  85. V. I. Shvedov, I. A. Kharizomenova, and A. N. Grinev, Inventor's Certificate No. 355171 (1971); Chem. Abstr.,78, 84246 (1973).

    Google Scholar 

  86. V. I. Shvedov, I. A. Kharizomenova, A. N. Grinev, V. K. Vasil'eva, and V. B. Romanova, Khim. Geterotsikl. Soedin., No. 7, 911 (1975).

    Google Scholar 

  87. V. I. Shvedov, I. A. Kharizomenova, and A. N. Grinev, Inventor's Certificate No. 366196 (1971); Chem. Abstr.,78, 159415 (1973).

    Google Scholar 

  88. V. I. Shvedov and A. N. Grinev, Khim. Geterotsikl. Soedin., No. 12, 1624 (1973).

    Google Scholar 

  89. H. Beyer, C. F. Kröger, G. Berg, C. Bischoff, and M. Zander, Ber.,89, 2230 (1956).

    Google Scholar 

  90. M. Chaykovsky, M. Lin, A. Rossowski, and E. I. Modest, J. Med. Chem.,16, 188 (1973).

    Google Scholar 

  91. M. Nakanishi, T. Furuta, and G. Hasegawa, Japanese Patent No. 7129868; Chem. Abstr.,75, 140817 (1971).

    Google Scholar 

  92. M. Nakanishi and Arimura, Japanese Patent No. 7217797; Chem. Abstr.,77, 152143 (1972).

    Google Scholar 

  93. P. Schmidt, K. Eichenberger, and E. Schweizer, West German Patent Application No. 1908497 (1969); Chem. Abstr.,72, 31837 (1970).

    Google Scholar 

  94. V. P. Araya, Indian J. Chem.,9, 904 (1971).

    Google Scholar 

  95. V. I. Shvedov, V. K. Ryzhkova, and A. N. Grinev, Khim. Geterotsikl. Soedin., No. 2, 329 (1967).

    Google Scholar 

  96. C. Hörig and H. Koch, Pharmazie,28, 553 (1975).

    Google Scholar 

  97. D. McDowell and D. B. Patrick. J. Org. Chem.,32, 2441 (1967).

    Google Scholar 

  98. K. Gewald and J. Schael, J. Prakt. Chem.,315, 39 (1973).

    Google Scholar 

  99. E. C. Taylor and J. G. Berger, J. Org. Chem.,32, 2376 (1967).

    Google Scholar 

  100. K. Gewald and G. Neumann, Z. Chem.,6, 261 (1966).

    Google Scholar 

  101. K. Gewald and G. Neumann, Ber.,101, 1933 (1968).

    Google Scholar 

  102. W. Ried and E. Nyondi-Bouguen, Ann., No. 1, 134 (1973).

    Google Scholar 

  103. H. G. Wippel, Melliand Textilber.,9, 1090 (1969).

    Google Scholar 

  104. K. Gewald and I. Hofmann, J. Prakt. Chem.,311, 402 (1969).

    Google Scholar 

  105. H. Eilingsfeld and R. Niess, West German Patent No. 2042984 (1972); Chem. Abstr.,76, 140495 (1972).

    Google Scholar 

  106. H. Eilingsfeld and R. Niess, West German Patent Application No. 2101701 (1972); Chem. Abstr.,77, 126613 (1972).

    Google Scholar 

  107. V. I. Shvedov, V. K. Vasil'eva, I. A. Kharizomenova, and A. N. Grinev, Khim. Geterotsikl. Soedin., No. 6, 767 (1975).

    Google Scholar 

  108. M. Robba, J. M. Lecomte, and M. Cugnon de Sevricourt, Bull. Soc. Chim. France, No. 8, 2864 (1974).

    Google Scholar 

  109. J. Fortea, J. Prakt. Chem.,317, 705 (1975).

    Google Scholar 

  110. M. S. Manhas, V. V. Rao, P. A. Seetharaman, D. Succardi, and J. Pazdera, J. Chem. Soc., C, No. 14, 1937 (1969).

    Google Scholar 

  111. H. J. Kabbe, Synthesis, No. 5, 268 (1972).

    Google Scholar 

  112. V. I. Shvedov, V. K. Ryzhkova, and A. N. Grinev, Khim. Geterotsikl. Soedin., No. 3, 459 (1967).

    Google Scholar 

  113. M. Robba and J. M. Lecomte, Comptes Rend.,264, 207 (1967).

    Google Scholar 

  114. M. Robba, J. M. Lecomte, and M. Cugnon de Sevricourt, Bull. Soc. Chim. France, No. 10, 3630 (1970).

    Google Scholar 

  115. M. Robba, J. M. Lecomte, and M. Cugnon de Sevricourt, Bull. Soc. Chim. France, No. 2, 587 (1975).

    Google Scholar 

  116. A. Cruceyra, V. Gomez, and R. Madronero, Ann. Quim., No. 1, 71 (1975); Chem. Abstr.,83, 131544 (1975).

    Google Scholar 

  117. J. Bourguignon, E. Gouegeon, G. QueGuiner, and P. Pastour, Bull. Soc. Chim. France, No. 2, 815 (1975).

    Google Scholar 

  118. F. Sauter, Monatsh.,99, 1507, 2100 (1968).

    Google Scholar 

  119. Centre d'Etudes pour l'Industrie Pharmaceutique, French Patent Application No. 2035768 (1971); Chem. Abstr.,75, 129830 (1971).

    Google Scholar 

  120. W. Ried and R. Giese, Ann.,713, 143 (1968).

    Google Scholar 

  121. W. Ried and R. Giese, Angew. Chem.,80, 122 (1968).

    Google Scholar 

  122. S. Rajappa, B. G. Advani, and R. Sreenivasan, Indian J. Chem.,12, 4 (1974).

    Google Scholar 

  123. F. Sauter, Monatsh.,101, 535 (1970).

    Google Scholar 

  124. Laboratorios Made S. A. Patronato de Investigacion Cientifica y Tecnica “Juan de la Cievra,” Spanish Patent No. 371373 (1973); Chem. Abstr.,79, 92269 (1973).

    Google Scholar 

  125. Z. Csüros, R. Soos, J. Palinkas, and I. Bitter, Acta Chim. Acad. Sci. Hung.,68, 397 (1971).

    Google Scholar 

  126. W. Ried and E. Kahr, Ann.,716, 219 (1973).

    Google Scholar 

  127. M. S. Manhas, D. S. Sharana, and S. G. Anim, J. Med. Chim.,15, 106 (1972); Chem. Abstr.,76, 107846 (1972).

    Google Scholar 

  128. L. Lorente, R. Madronero, and S. Vega, Ann. Quim., No. 974 (1974); Chem. Abstr.,83, 178980 (1975).

    Google Scholar 

  129. A. Klau, Dissertation, Universität Erlangen-Nürnberg (1974).

  130. V. I. Shvedov and A. N. Grinev, Khim. Geterotsikl. Soedin., No. 4, 515 (1966).

    Google Scholar 

  131. N. K. Son, R. Pinel, and Y. Mollier, Bull. Soc. Chim. France, No. 4, 1359 (1974).

    Google Scholar 

  132. M. Robba, J. M. Lecomte, and M. Cugnon de Sevricourt, Bull. Soc. Chim. France, No. 2, 592 (1975).

    Google Scholar 

  133. B. Narr and E. Woitin, West German Patent Application No. 2200764 (1973); Chem. Abstr.,79, 92270 (1973).

    Google Scholar 

  134. Laboratorios Made S. A., Patronato de Investigaction Cientifica y Tecnica “Juan de la Cievra,” Spanish Patent No. 381459 (1972); Chem. Abstr., 79, 92280 (1973).

    Google Scholar 

  135. M. S. Manhas and S. D. Sharana, J. Heterocycl. Chem.,8, 1051 (1971).

    Google Scholar 

  136. M. Robba, J. M. Lecomte, and M. Cugnon de Sevricourt, J. Heterocycl. Chem.,12, 525 (1975).

    Google Scholar 

  137. V. P. Araya, Indian J. Chem.,10, 1141 (1972).

    Google Scholar 

  138. L. Capuano, M. Welfer, and R. Zander, Ber.,102, 3698 (1969).

    Google Scholar 

  139. A. A. Dobosh, S. M. Khripak, and I. V. Smolanka, Khim. Geterotsikl. Soedin., No. 4, 486 (1974).

    Google Scholar 

  140. F. Sauter and W. Deinhammer, Monatsh.,104, 1593 (1973).

    Google Scholar 

  141. F. Sauter and W. Deinhammer, Monatsh.,105, 1249 (1974).

    Google Scholar 

  142. S. M. Khripak, A. A. Dobosh, and I. V. Smolanka, Khim. Geterotsikl. Soedin., No. 4, 567 (1973).

    Google Scholar 

  143. S. M. Khripak, A. A. Dobosh, and I. V. Smolanka, Ukr. Khim. Zh.,39, 402 (1973).

    Google Scholar 

  144. F. Sauter and W. Deinhammer, Monatsh.,105, 452 (1974).

    Google Scholar 

  145. F. Sauter, Monatsh.,105, 558, 863, 882 (1974).

    Google Scholar 

  146. F. Sauter, W. Deinhammer, and P. Stanetty, Monatsh.,105, 1258 (1974).

    Google Scholar 

  147. I. V. Smolanka, A. A. Dobosh, and S. M. Khripak, Khim. Geterotsikl. Soedin., No. 9, 1289 (1973).

    Google Scholar 

  148. I. V. Smolanka, A. A. Dobosh, and S. M. Khripak, Khim. Geterotsikl. Soedin., No. 1, 134 (1974).

    Google Scholar 

  149. Centre d'Etudes pour l'Industrie Pharmaceutique, West German Patent Application No. 226422 (1973); Chem. Abstr.,79, 78837 (1973).

    Google Scholar 

  150. V. I. Shvedov, I. A. Kharizomenova, and A. N. Grinev, Inventor's Certificate No. 355167 (1971); Chem. Abstr.,78, 72189 (1973).

    Google Scholar 

  151. T. Hirohashi, S. Hironi, S. Inaba, and H. Yamamoto, West German Patent Application No. 231016 (1973); Chem. Abstr.,79, 137191 (1973).

    Google Scholar 

  152. M. Nakanishi and T. Tahara, Japanese Patent No. 7511398; Chem. Abstr.,83, 193369 (1975).

    Google Scholar 

  153. J. Fortea, Afinidad,31, 133 (1974); Chem. Abstr.,81, 91282 (1974).

    Google Scholar 

  154. P. I. Abramenko, Khim. Geterotsikl. Soedin., No. 3, 334 (1965).

    Google Scholar 

  155. Y. Kuwada, K. Meguro, Y. Sato, and T. Fugono, West German Patent Application No. 2435025 (1974); Chem. Abstr.,82, 156252 (1975).

    Google Scholar 

  156. V. I. Shvedov, I. A. Kharizomenova, and A. N. Grinev, Inventor's Certificate No. 364613 (1971); Chem. Abstr.,78, 159580 (1973).

    Google Scholar 

  157. M. Shiroki, Japanese Patent Application No. 7558098; Chem. Abstr.,83, 193311 (1975).

    Google Scholar 

  158. V. P. Araya, Indian J. Chem.,9, 1209 (1971).

    Google Scholar 

  159. O. Hromatka and D. Binder, Monatsh.,104, 704 (1973).

    Google Scholar 

  160. O. Hromatka, D. Binder, and P. Stanetty, Monatsh.,104, 709 (1973).

    Google Scholar 

  161. O. Hromatka, D. Binder, C. R. Noe, P. Stanetty, and W. Veit, Monatsh.,104, 715 (1973).

    Google Scholar 

  162. T. Hirohashi, H. Sato, S. Inaba, and H. Yamamoto, Japanese Patent Application No. 7410098; Chem. Abstr.,83, 10172 (1975).

    Google Scholar 

  163. M. Nakanishi, K. Araki, T. Tahara, and M. Shiroki, West German Patent Application No. 2107356 (1971); Chem. Abstr.,75, 129847 (1971).

    Google Scholar 

  164. M. Nakanishi, K. Araki, T. Tahara, and M. Shiroki, Japanese Patent Application No. 7322490; Chem. Abstr.,79, 18777 (1973).

    Google Scholar 

  165. T. Hirohashi, H. Sato, S. Inaba, and H. Yamamoto, Japanese Patent Application No. 7481386; Chem. Abstr.,86, 57748 (1975).

    Google Scholar 

  166. Laboratorios Made S. A. Patronato de Investigacion Cientifica y Tecnica “Juan de la Cievra,” Spanish Patent No. 393101 (1974); Chem. Abstr.,82, 97405 (1975).

    Google Scholar 

  167. R. Madronero, J. DelRio, A. Garcia, and C. Martinez, West German Patent Application No. 2319174; (1974); Chem. Abstr.,82, 4321 (1975).

    Google Scholar 

  168. T. Hirohashi, H. Sato, S. Inaba, and H. Yamamoto, Japanese Patent Application No. 7375591; Chem. Abstr.,80, 121014 (1974).

    Google Scholar 

  169. J. Hellerbach, P. Zeller, D. Binder, and O. Hromatka, West German Patent Application No. 2405682 (1974); Chem. Abstr.,81, 136196 (1974).

    Google Scholar 

  170. J. Hellerbach, P. Zeller, D. Binder, and O. Hromatka, East German Patent No. 112454 (1975).

  171. M. Nakanishi, K. Araki, T. Tahara, and M. Shiroki, Japanese Patent Application No. 7449994; Chem. Abstr.,81, 77980 (1974).

    Google Scholar 

  172. O. Hromatka and D. Binder, Monatsh.,104, 1105 (1973).

    Google Scholar 

  173. M. Nakanishi, T. Tahara, K. Araki, and M. Shiroki, Japanese Patent Application No. 7397891; Chem. Abstr.,80, 121019 (1974).

    Google Scholar 

  174. M. Nakanishi, M. Shiroki, T. Tahara, and K. Araki, Japanese Patent Application No. 7311392; Chem. Abstr.,82, 57752 (1975).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Chemistry Faculty, Dresden TechnicalUniversity, USSR

    K. Gewald

Authors
  1. K. Gewald
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1299–1315, October, 1976.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Gewald, K. Methods for the synthesis of 2-aminothiophenes and their reactions (review). Chem Heterocycl Compd 12, 1077–1090 (1976). https://doi.org/10.1007/BF00945583

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00945583

Keywords

Search

Navigation