Skip to main content
SpringerLink
Log in

1,4-Diazabicyclo[2.2.2]octanes (review)

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The literature data and our own experimental data on the synthesis and physical and chemical properties of 1,4-diazabicyclo[2.2.2]octanes as compared with their 4-deaza analogs (quinuclidines) are correlated. Methods for the practical utilization of the diazabicyclic systems are examined.

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. L. N. Yakhontov, Usp. Khim.,38, 1038 (1969).

    Google Scholar 

  2. L. N. Yakhontov, Advances in Heterocyclic Chemistry, Vol. 11 (1970), p. 473.

    Google Scholar 

  3. L. N. Yakhontov and E. E. Mikhlina, Khim. Geterotsikl. Soedin., No. 8, 1011 (1975).

    Google Scholar 

  4. M. D. Mashkovskii (Mashkovskyi) and L. N. Yakhontov. Fortschr. Arzneimittelforsch.,13, 293 (1969).

    Google Scholar 

  5. E. E. Mikhlina and M. V. Rubtsov. Zh. Obshch. Khim.,30, 163 (1960).

    Google Scholar 

  6. M. V. Rubtsov, M. D. Mashkovskii, E. E. Mikhlina, K. A. Zaitseva, and V. Ya. Vorob'eva, Med. Prom., No. 10, 14 (1962).

    Google Scholar 

  7. E. E. Mikhlina, V. Ya. Vorob'eva, and M. V. Rubtsov, Zh. Obshch. Khim.,31, 2609 (1961).

    Google Scholar 

  8. E. S. Nikit-skaya, E. I. Levkoeva, I. M. Sharapov, V. S. Usovskaya, A. S. Vlasov, T. E. Kukushkina, L. N. Yakhontov, and M. V. Rubtsov, Khim. Farmats. Zh., No. 10, 58 (1970).

    Google Scholar 

  9. E. S. Nikit-skaya, L. M. Sharapov. M. D. Mashkovskii, E. I. Levkoeva, A. S. Vlasov, T. E. Kukushkina, and L. N. Yakhontov, Khim. Farmats. Zh., No. 8, 59 (1974).

    Google Scholar 

  10. M. É. Kaminka, E. E. Mikhlina, V. Ya. Vorob'eva, A. D. Yanina, N. A. Komarova, M. D. Mashkovskii, and L. N. Yakhontov, Khim. Farmats. Zh., No. 6, 48 (1976).

    Google Scholar 

  11. L. N. Yakhontov and M. V. Rubtsov. Zh, Obshch. Khim.,27, 72 (1957).

    Google Scholar 

  12. E. I. Levkoeva, E. S. Nikit-skaya, and L. N. Yakhontov, Dokl. Akad. Nauk SSSR,192, 342 (1970).

    Google Scholar 

  13. E. Cherbuliez and E. Feer, Helv. Chim. Acta,5, 678 (1922).

    Google Scholar 

  14. A. W. Hofmann. Proc. Roy. Soc., London,9, 153 (1859).

    Google Scholar 

  15. O. Hromatka, Ber.,75B, 1302 (1942).

    Google Scholar 

  16. O. Hromatka and O. Kraupp, Monatsh.,82, 880 (1951).

    Google Scholar 

  17. F. G. Mann and F. G. Baker, J, Chem. Soc., 1881 (1957).

  18. J. H. Krause, R. K. Smith, and E. C. Herrick, British Patent No. 871754 (1958); Chem. Abstr.,56, 3492 (1962).

    Google Scholar 

  19. E. C. Herrick. US Patent No. 2937176 (1960): Chem. Abstr.,54, 21, 145 (1960).

    Google Scholar 

  20. A. Anderson, D. K. Kurgan, S. A. Giller, and M. V. Shimanskaya, Piperazine [in Russian], Izd. Akad. Nauk LatvSSR, Riga (1965).

    Google Scholar 

  21. H. G. Muhlbauer and M. Lichtenwalter, US Patent No. 3285920 (1966); Chem. Abstr.,66, 76033 (1967).

    Google Scholar 

  22. P. M. F. Matell, J. T. Tonquist, and O. R. Steijner, US Patent No. 3242183 (1966); Chem Abstr.,64, 15898 (1966).

    Google Scholar 

  23. L. A. Hamilton and P. S. Landis, US Patent No. 3369019 (1968): Chem. Abstr.,69, 43938 (1968).

    Google Scholar 

  24. F. G. Mann and D. P. Mukherjee, J. Chem. Soc., 2298 (1949).

  25. T. Ishiguro, E. Kitamura, M. Matsumura, and H. Ogawa, J. Pharm. Soc. Japan,75, 1370 (1955).

    Google Scholar 

  26. W. H. Brader, US Patent No. 3056788 (1962): Chem. Abstr.,59, 1661 (1963).

    Google Scholar 

  27. W. H. Brader, US Patent No. 3157657 (1964): Chem. Abstr.,62, 4038 (1965).

    Google Scholar 

  28. A. Farkas, J. M. Hersh, and R. L. Mascioli, US Patent No. 3167555 (1965); Chem. Abstr.,69, 59287 (1968).

    Google Scholar 

  29. S. Yamada and T. Kurano, US Patent No. 3375252 (1968); Chem. Abstr.,69, 59287 (1968).

    Google Scholar 

  30. W. H. Brader and R. L. Rowton, US Patent No. 3297701 (1967); Chem. Abstr.,66, 115734 (1967).

    Google Scholar 

  31. W. H. Brader, Belgian Patent No. 668777 (1966); Chem. Abstr.,65, 13735 (1966).

    Google Scholar 

  32. M. D. Oakes, L. L. Upson, and M. H. Ziv, US Patent No. 3772293 (1973); Chem. Abstr.,80, 48039 (1974).

    Google Scholar 

  33. I. Jezo and I. Lusak, Czechoslovakian Patent No. 139281 (1970); Chem. Abstr.,76, 59658 (1972).

    Google Scholar 

  34. T. Kurano, H. Saito, and S. Jamada, Japanese Patent No. 16512 (1967); Chem. Abstr.,69, 2959 (1968).

    Google Scholar 

  35. A. Farkas, US Patent No. 2950282 (1960); Chem. Abstr.,55, 9438 (1961).

    Google Scholar 

  36. R. Murakami, S. Kato, and H. Mitarashi, Japanese Patent No. 7476897 (1974); Chem. Abstr.,82, 31351 (1975).

    Google Scholar 

  37. F. G. Mann and A. Senior, J. Chem. Soc., 4476 (1954).

  38. W. W. Zewis and F. A. Weipert, US Patent No. 3112321 (1961); Chem. Abstr.,60, 6856 (1964).

    Google Scholar 

  39. S. M. McElvain and L. W. Bannister, J. Am. Chem. Soc.,76, 1126 (1954).

    Google Scholar 

  40. S. M. McElvain and E. H. Pryde, J. Am. Chem. Soc.,71, 326 (1949).

    Google Scholar 

  41. S. M. McElvain and T. Lies, J. Am. Chem. Soc.,82, 164 (1960).

    Google Scholar 

  42. L. B. Mrachkovskaya and L. N. Yakhontov, Khim. Geterotsikl. Soedin., No. 6, 845 (1976).

    Google Scholar 

  43. M. V. Rubtsov and M. I. Dorokhova, Zh. Obshch. Khim.,23, 706 (1953).

    Google Scholar 

  44. E. Renk and C. Grob, Helv. Chim. Acta,37, 2119 (1954).

    Google Scholar 

  45. C. Mannich and E. Ganz, Ber.,55, 3486 (1954).

    Google Scholar 

  46. L. N. Yakhontov, L. B. Mrachkovskaya, A. I. Ermakov, K. F. Turchin, and T. F. Vlasova, Zh. Org. Khim.,10, 868 (1974).

    Google Scholar 

  47. L. B. Mrachkovskaya, K. F. Turchin, and L. N. Yakhontov, Zh. Org, Khim.,11, 420 (1975).

    Google Scholar 

  48. L. B. Mrachkovskaya, O. S. Anisimova, K. F. Turchin, and L. N. Yakhontov, Zh. Org. Khim.,12, 914 (1976).

    Google Scholar 

  49. L. B. Mrachkovskaya, Master's Dissertation, Moscow (1975).

  50. L. B. Mrachkovskaya, K. F. Turchin, and L. N. Yakhontov, Khim. Geterotsikl. Soedin.,(in press).

  51. E. Eliel, N. Allinger, S. Angyal, and T. Morrison, Conformational Analysis, Wiley (1965).

  52. A. Ladenburg, Ber.,30, 1587, 3043 (1897).

    Google Scholar 

  53. T. S. Moore and Y. Doubleday, J. Chem. Soc.,119, 1170 (1921).

    Google Scholar 

  54. L. R. Davidenkov, USSR Author's Certificate No. 255287 (1967); Byul. Izobr., No. 46, 29 (1969).

  55. R. F. Evans, Chem. Ind., 915 (1958).

  56. L. B. Mrachkovskaya and L. N. Yakhontov, Khim. Geterotsikl. Soedin., No. 6, 856 (1975).

    Google Scholar 

  57. L. B. Mrachkovskaya, K. F. Turchin, and L. N. Yakhontov, Khim. Geterotsikl. Soedin., No. 2, 272 (1976).

    Google Scholar 

  58. A. Farkas, G. A. Mills, W. E. Erner, and J. B. Maerker, J. Chem. Eng. Data,4., 334 (1959).

    Google Scholar 

  59. A. Farkas, G. A. Mills, W. E. Erner, and J. B. Maerker, Ind. Eng. Chem.,51, 1299 (1959).

    Google Scholar 

  60. A. Farkas, R. L. Mascioli, F. Miller, and P. F. Strohm, J. Chem. Eng. Data,13, 278 (1968).

    Google Scholar 

  61. Triethylenediamine. Properties, Reactions, and Applications, Houdry Process Corp. (1965).

  62. Triethylenediamine, Houdry Process Corp. (1971).

  63. W. L. Mosby, Heterocyclic Systems with Bridgehead Nitrogen Atoms, New York-London (1961).

  64. P. Bischof, J. A. Hashmall, E. Heilbronner, and V. Hornung, Tetrahedron Lett., 4025 (1969).

  65. E. Heilbronner and K. A. Muszkat, J. Am. Chem. Soc.,92, 3818 (1970).

    Google Scholar 

  66. R. Hoffmann, A. Imamura, and J. W. Hehre, J. Am. Chem. Soc.,90, 1499 (1968).

    Google Scholar 

  67. A. M. Halpern, J. L. Roebber, and K. Weiss, J. Chem. Phys.,49, 1348 (1968).

    Google Scholar 

  68. M. P. Marzocchi, G. Sbrana, and G. Zerbi, J. Am. Chem. Soc.,87, 1429 (1965).

    Google Scholar 

  69. T. M. McKinney, and D. H. Geske, J. Am. Chem. Soc.,87, 3013 (1965).

    Google Scholar 

  70. T. Wada, E. Kishida, J. Tomiie, H. Suga, S. Seki, and J. Nitta, Bull. Chem. Soc. Japan,33, 1317 (1960).

    Google Scholar 

  71. E. S. Weiss, A. S. Parkes, E. R. Nixon, and R. E. Hughes, J. Chem. Phys.,41, 3759 (1964).

    Google Scholar 

  72. P. Bruesch and H. H. Günthard, Spectrochim. Acta,22, 877 (1966).

    Google Scholar 

  73. Ch.-S. Chang and E. F. Westrum, J. Phys. Chem.,64, 1551 (1960).

    Google Scholar 

  74. J. C. Trowbridge, Abstract of Candidate's Dissertation,24, 2291 (1963).

    Google Scholar 

  75. J. C. Trowbridge and E. F. Westrum, J. Phys. Chem.,67, 2381 (1963).

    Google Scholar 

  76. P. A. Reynolds, Mol. Phys.,28, 633 (1974).

    Google Scholar 

  77. J. Wagner, Z. Phys. Chem.,48b, 316 (1941).

    Google Scholar 

  78. T. M. McKinney, Spectrochim. Acta,25A, 501 (1969).

    Google Scholar 

  79. A. M. Halpern, Chem. Phys. Lett.,6, 296 (1970).

    Google Scholar 

  80. P. J. Haigh and L. Guibe, Compt. Rend.,261, 2328 (1965).

    Google Scholar 

  81. A. Zussman and S. Alexander, J. Chem. Phys.,48, 3534 (1968).

    Google Scholar 

  82. G. W. Smith, J. Chem. Phys.,43, 4325 (1965).

    Google Scholar 

  83. J. L. Colot, J. Mol. Struct.,13, 129 (1972).

    Google Scholar 

  84. L. N. Beska, J. Chem. Phys.,38, 1685 (1963).

    Google Scholar 

  85. J. C. Trowbridge and E. F. Westrum, J. Phys. Chem. Solids,64, 1551 (1960).

    Google Scholar 

  86. H. Suga, M. Sugisaki, and S. Seki, Mol. Crystals,1, 377 (1966).

    Google Scholar 

  87. M. Parris, P. S. Raybin, and L. C. Labowitz, J. Chem. Eng. Data,9, 221 (1964).

    Google Scholar 

  88. H. K. Hall, J. Org. Chem.,28, 223 (1963).

    Google Scholar 

  89. L. N. Yakhontov, K. F. Turchin, E. E. Mikhlina, V. Ya. Vorob'eva, A. D. Yanina, and Yu. N. Sheinker, in: Problems of Stereochemistry [in Russian], No. 1 (1971), p. 117.

    Google Scholar 

  90. T. K. Adler and A. Albert, J. Chem. Soc., 1794 (1960).

  91. J. W. Larsen, G. L. Bertrand, and L. G. Helper, J. Chem. Eng. Data,11, 595 (1966).

    Google Scholar 

  92. P. Paoletti, J. H. Stern, and A. Vacca, J. Phys. Chem.,69, 3759 (1965).

    Google Scholar 

  93. J. C. Hsieh, P. J. Inglefield, and W.-Y. Wen, J. Solution Chem.,3, 351 (1974).

    Google Scholar 

  94. J. C. Hsieh, P. J. Inglefield, and W.-Y. Wen, J. Solution Chem.,3, 103 (1974).

    Google Scholar 

  95. R. Pottel and U. Kaatz, Ber. Bunsenges. Phys. Chem.,73, 437 (1969).

    Google Scholar 

  96. J. F. Coetzee and G. R. Padmanabhan, J. Am. Chem. Soc.,87, 5005 (1965).

    Google Scholar 

  97. T. E. Mead, J. Phys. Chem.,66, 2149 (1962).

    Google Scholar 

  98. J. L. Sudmeier and C. N. Leiley, Anal. Chem.,36, 1698 (1964).

    Google Scholar 

  99. H. J. Suhr, J. Mol. Struct.,1, 295 (1968).

    Google Scholar 

  100. D. Cook, Can. J. Chem.,42, 2292 (1964).

    Google Scholar 

  101. O. Hromatka and E. Engel, Ber.,76B, 712 (1943).

    Google Scholar 

  102. S. Oae, B. Hovarth, C. Zalut, and R. Harris, J. Org. Chem.,24, 1348 (1959).

    Google Scholar 

  103. H. G. Viehe, S. I. Miller, and J. H. Dickstein, Angew. Chem.,76, 537 (1964).

    Google Scholar 

  104. S. D. Ross and M. Finkelstein, J. Am. Chem. Soc.,85, 2603 (1963).

    Google Scholar 

  105. S. D. Ross, J. J. Bruno, and R. C. Peterson, J. Am. Chem. Soc.,85, 3999 (1963).

    Google Scholar 

  106. J. A. Ford and C. V. Wilson, J. Org. Chem.,28, 875 (1963).

    Google Scholar 

  107. N. Kornblum and F. W. Stuchal, J. Am. Chem. Soc.,92, 1804 (1970).

    Google Scholar 

  108. T. P. Abbiss and T. G. Mann, J. Chem. Soc., 2248 (1964).

  109. P. Froyen and R. F. Hudson, Acta Chem. Scand.,27, 4001 (1973).

    Google Scholar 

  110. R. G. Kallen and W. P. Jencks, J. Biol. Chem.,241, 5864 (1966).

    Google Scholar 

  111. H. H. Sisler. H. S. Ahuja, and N. L. Smith, J. Org. Chem.,26, 1819 (1961).

    Google Scholar 

  112. P. W. Inward and W. P. Jencks, J. Biol. Chem.,240, 1986 (1965).

    Google Scholar 

  113. K. Brack, West German Patent No. 1904349 (1969); Chem. Abstr.,71, 102642 (1969).

    Google Scholar 

  114. S. Dunstan and H. B. Henbest, J. Chem. Soc., 4880 (1957).

  115. S. Oae, J. Onishi, S. Kozuka, and W. Tagaku, Bull. Chem. Soc. Japan,39, 364 (1966).

    Google Scholar 

  116. E. C. Herrick, US Patent No. 2964526 (1960): Chem. Abstr.,55, 11446 (1961).

    Google Scholar 

  117. A. M. Halpern and K. Weiss, J. Am. Chem. Soc.,90, 6297 (1968).

    Google Scholar 

  118. S. Gran and C. Roeming, Acta Chem. Scand.,22, 1686 (1968).

    Google Scholar 

  119. A. M. Halpern and K. Weiss, J. Phys. Chem.,72, 3863 (1968).

    Google Scholar 

  120. E. C. Ashby, J. Am. Chem. Soc.,86, 1882 (1964).

    Google Scholar 

  121. E. C. Ashby, US Patent No. 3159626 (1964); Chem. Abstr.,62, 7795 (1965).

    Google Scholar 

  122. A. R. Gatti and T. Wartik, Inorg. Chem.,5, 2075 (1966).

    Google Scholar 

  123. M. D. Marshall and R. M. Hant, Nucl. Abstr.,21, 170 (1967).

    Google Scholar 

  124. J. M. Van Paassehen and R. A. Geanangel, Can. J. Chem.,53, 723 (1975).

    Google Scholar 

  125. V. V. Zharkov, A. V. Zhitinkina, F. A. Zhokhova, Zh. Fiz. Khim.,44, 223 (1970).

    Google Scholar 

  126. S. W. Tucker and S. Walker, Trans. Faraday Soc.,62, 2690 (1966).

    Google Scholar 

  127. J. A. Dilts and E. C. Ashby, Inorg. Chem.,9, 855 (1970).

    Google Scholar 

  128. R. K. Bartlett, H. S. Turner, R. J. Warne, M. A. Joung, and J. J. Lawrenson, J. Chem. Soc., A, 479 (1966).

  129. C. S. L. Baker, D. Barnard, and M. Porter, Rubber Res.,22, 317 (1969).

    Google Scholar 

  130. B. F. Conway and H. P. Dhar, Electrochim. Acta,19, 445 (1974).

    Google Scholar 

  131. R. A. Baldwin and R. M. Washburn, J. Org. Chim.,26, 3549 (1961).

    Google Scholar 

  132. A. Farkas and H. Graboys, US Patent No. 3037026 (1962); Chem. Abstr.,57, 13778 (1962).

    Google Scholar 

  133. A. K. Banerjee, L. M. Vallarino, and J. V. Quagliano, Coord. Chem. Rev.,1, 239 (1966).

    Google Scholar 

  134. G. J. Tennenhouse and J. C. Bailar, J. Inorg. Nucl. Chem.,28, 682 (1966).

    Google Scholar 

  135. G. Brun and G. Jourdan, Compt. Rend.,279C, 129 (1974).

    Google Scholar 

  136. H. M. Hilliard, D. D. Axtell, M. M. Gilbert, and J. T. Yoke, J. Inorg. Nucl. Chem.,31, 2117 (1969).

    Google Scholar 

  137. H. M. Hilliard and J. T. Yoke, Inorg. Chem.,5, 57 (1966).

    Google Scholar 

  138. G. Schwarzenbach, B. Maissen, and H. Ackermann, Helv. Chim. Acta,35, 2333 (1952).

    Google Scholar 

  139. C. G. Screttas and J. F. Eestham, J. Am. Chem. Soc.,87, 3276 (1965).

    Google Scholar 

  140. V. L. Goedken, Abstract of Candidate's Dissertation, B,30, 543 (1969).

    Google Scholar 

  141. E. D. Stevens, and J. T. Yoke, Inorg. Chim. Acta,4, 244 (1970).

    Google Scholar 

  142. Y. V. Quagliano, A. K. Banerjee, V. L. Goedken, and L. M. Vallarino, J. Am. Chem. Soc.,92, 482 (1970).

    Google Scholar 

  143. S. P. Patterman, I. L. Karle, G. D. Stucky, J. Am. Chem. Soc.,92, 1150 (1970).

    Google Scholar 

  144. W. H. Glase, Chem. Rev.,4B, 161 (1968).

    Google Scholar 

  145. L. A. Nikolaev, Zh. Fiz. Khim.,28, 275 (1954).

    Google Scholar 

  146. T. Takahashi, Japanese Patent No. 7461066 (1974); Chem. Abstr.,81, 180367 (1974).

    Google Scholar 

  147. W. H. Brader, S. B. Cawitt, and R. M. Gispon, French Patent No. 1530236 (1968); Chem. Abstr.,71, 60714 (1969).

    Google Scholar 

  148. A. A. Oswald and D. L. Guertin, J. Org, Chem.,28, 651 (1963).

    Google Scholar 

  149. A. Farkas and E. C. Herrick, US Patent No. 3038903 (1962); Chem, Abstr.,57, 13776 (1962).

    Google Scholar 

  150. A. A. Oswald and F. Noel, US Patent No. 3252979 (1966); Chem. Abstr.,65, 7057 (1966).

    Google Scholar 

  151. A. A. Oswald, F. Noel, and A. J. Stephenson, J. Org. Chem.,26, 3969 (1961).

    Google Scholar 

  152. C. Quannes, and T. Wilson, J. Am. Chem. Soc.,90, 6527 (1968).

    Google Scholar 

  153. E. A. Ogruzlo and C. W. Tang, J. Am. Chem. Soc.,92, 5034 (1970).

    Google Scholar 

  154. E. F. Curragh, H. B. Henbest, and A. Tomas, J. Chem. Soc., 3559 (1960).

  155. L. A. Hull, D. H. Rosenblatt, W. P. Giordano, G. T. Davis, C. K. Mann, and S. B. Milliken, J. Phys. Chem.,73, 2147 (1969).

    Google Scholar 

  156. D. M. Gardner, R. Helitzer, and D. H. Rosenblatt, J. Org. Chem.,32, 1115 (1967).

    Google Scholar 

  157. W. H. Dennis, L. D. Bull, and D. H. Rosenblatt, J. Org. Chem.,32, 3783 (1967).

    Google Scholar 

  158. L. A. Hull, G. T. Davis, D. H. Rosenblatt, H. K. R. Williams, and R. G. Weglein, J. Am. Chem. Soc.,89, 1163 (1967).

    Google Scholar 

  159. S. F. Nelsen and J. M. Buschek, J. Am. Chem. Soc.,96, 6424 (1974).

    Google Scholar 

  160. P. Brenneisen, C. A. Grob, R. A. Jackson, and M. Ohta, Helv. Chim. Acta,48, 146 (1965).

    Google Scholar 

  161. R. Huisgen and W. Kolbeck, Tetrahedron Lett., 783 (1965).

  162. E. Koch, Tetrahedron,26, 3503 (1970).

    Google Scholar 

  163. R. F. Bartholomew and R. S. Davidson, Chem. Commun., 1174 (1970).

  164. H. Henecka, V. Hoerlein, and K. H. Gisse, Angew. Chem.,72, 960 (1960).

    Google Scholar 

  165. O. Hromatko and C. Skopalik, Monatsh.,83, 39 (1952).

    Google Scholar 

  166. H. K. Hall, US Patent No. 3165482 (1965);62, 7955 (1965).

  167. T. T. Suruta and M. Ishimori, Japanese Patent No. 6904792 (1969); Chem. Abstr.,71, 30817 (1969).

    Google Scholar 

  168. G. A. Vorob'eva, G. M. Trofimova, and A. A. Berlin, and N. S. Enikolopyan, Dokl. Akad. Nauk SSSR,214, 373 (1974).

    Google Scholar 

  169. W. G. Lloyd, US Patent No. 3265663 (1966); Chem. Abstr.,65, 18722 (1966).

    Google Scholar 

  170. A. J. Kirby and A. G. Varvoglis, J. Chem. Soc., B, 135 (1968).

    Google Scholar 

  171. N. Kornblum and F. W. Stuchal, J. Am. Chem. Soc.,92, 1804 (1970).

    Google Scholar 

  172. W. A. Khan, A. G. Giumanini, and R. A. Lepley, Chim. Ind., (Milano),49, 1342 (1967).

    Google Scholar 

  173. A. R. Lepley and W. A. Khan, J. Org. Chem.,33, 4362 (1968).

    Google Scholar 

  174. W. E. Erner, US Patent No. 3335143 (1967); Chem. Abstr.,68, 21507 (1968).

    Google Scholar 

  175. J. R. L. Smith and Z. A. Malik, J. Chem. Soc., B, 920 (1970).

    Google Scholar 

  176. J. C. Philips, Y. V. Swisher, D. Haidukewich, and O. Morales, Chem. Commun., 22 (1971).

  177. V. R. Verlan, Tetrahedron Lett., 985 (1969).

  178. W. P. Jencks and M. Gilchrist, J. Am. Chem. Soc.,87, 3199 (1965).

    Google Scholar 

  179. G. W. Jameson and J. M. Lawlor, J. Chem. Soc., 53 (1970).

  180. J. Furuya, S. Goto, K. Itoho, I. Urasaki, and A. Morita, Tetrahedron,24, 2367 (1968).

    Google Scholar 

  181. E. Kaiser and Yun, J. Org. Chem.,35, 1348 (1970).

    Google Scholar 

  182. B. S. Huang, E. J. Parish, and D. N. Miles, J. Org. Chem.,39, 2647 (1974).

    Google Scholar 

  183. D. M. Burness and B. D. Wilson, US Patent No. 3396127 (1968): Chem. Abstr.,69, 77278 (1968).

    Google Scholar 

  184. R. C. Doss and W. B. Reynolds, US Patent No. 3018619 (1962); Chem. Abstr.,56, 15719 (1962).

    Google Scholar 

  185. W. E. Erner, US Patent No. 3073827 (1963): Chem. Abstr.,59, 643 (1963).

    Google Scholar 

  186. Mobil Oil Corp., British Patent No. 1047885 (1966); Chem. Abstr.,66, 115735 (1967).

    Google Scholar 

  187. G. Hoelrle, P. Ulrich, H. P. Schaub, and H. H. Bosshard, Swiss Patent No. 423708 (1967); Chem. Abstr.,68, 40935 (1968).

    Google Scholar 

  188. R. Entschel, Swiss Patent No. 546269 (1974); Chem. Abstr.,81, 38935 (1974).

    Google Scholar 

  189. R. F. Strohm, US Patent No. 3350401 (1967); Chem. Abstr.,68, 2927 (1968).

    Google Scholar 

  190. R. C. Doss and J. P. Blackwell, US Patent No. 3019081 (1962); Chem. Abstr.,57, 1854 (1962).

    Google Scholar 

  191. A. Farkas and K. G. Flinn, J. Am. Chem. Soc.,82, 642 (1960).

    Google Scholar 

  192. J. W. Baker and J. B. Holdsworthy, J. Chem. Soc., 713 (1947).

  193. F. Miller, US Patent No. 3213096 (1965); Chem. Abstr.,63, 18115 (1965).

    Google Scholar 

  194. A. Farkas and P. F. Strohm, Ind. Eng. Chem. Fundamentals,4, 32 (1965).

    Google Scholar 

  195. R. G. Roemer, C. J. W. Van Ginkel, and B. Griepink, Microchim. Acta, 1 (1974).

  196. J. J. Sweeney, French Patent No. 1546618 (1968); Chem. Abstr.,71, 50848 (1969).

    Google Scholar 

  197. A. G. Schering, East German Patent No. 1090803 (1960); Chem. Abstr.,56, 6118 (1962).

    Google Scholar 

  198. P. P. Nicholas, West German Patent No. 2307971 (1974): Chem. Abstr.,82, 18377 (1975).

    Google Scholar 

  199. S. L. Friess, J. Am. Chem. Soc.,79, 3269 (1957).

    Google Scholar 

  200. M. E. Goldberg and H. E. Jonson, Toxicol. Appl. Pharmacol.,4, 545 (1962).

    Google Scholar 

  201. W. E. Erner, US Patent No. 3010963 (1959); Chem. Abstr.,56, 10167 (1962).

    Google Scholar 

  202. R. B. Moffet, US Patent No. 3144455 (1964); Chem. Abstr.,61, 9511 (1964).

    Google Scholar 

  203. R. B. Moffet, J. Med. Chem.,7, 450 (1964).

    Google Scholar 

  204. R. B. Moffet, US Patent No. 3144446 (1964); Chem. Abstr.,61, 10752 (1964).

    Google Scholar 

  205. A. I. Andriadze, Tr. Inst. Klin. Éksp. Kardiol., Akad. Nauk GruzSSR,9, 69 (1969).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. S. Ordzhonikidze All-Union Scientific-Research Pharmaceutical-Chemistry Institute, Moscow

    L. N. Yakhontov & L. B. Mrachkovskaya

Authors
  1. L. N. Yakhontov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. L. B. Mrachkovskaya
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 723–738, June, 1976.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Yakhontov, L.N., Mrachkovskaya, L.B. 1,4-Diazabicyclo[2.2.2]octanes (review). Chem Heterocycl Compd 12, 607–619 (1976). https://doi.org/10.1007/BF00742440

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00742440

Keywords

Search

Navigation