Abstract
It has been shown that amino derivatives of sulfanilamide, and also some functionally substituted primary arylamines and cycloalkylamines, undergo heterocyclization with triethyl orthoformate and sodium azide with the formation of 1-monosubstituted tetrazoles. Primary amines of the azole series, 5-aminotetrazole, 5-amino-1-methyltetrazole, 4-amino-1,2,4-triazole, and also less basic arylamines (4-fluoro-3-nitroaniline, 2,6-dibromo-4-nitroaniline) did not react. An efficient method of introducing an amino group into position C(5) of the tetrazole ring of 1-aryltetrazoles is proposed, based on alkaline decomposition of the tetrazole ring and heterocyclization of the resulting N-arylcyanamides on interaction with ammonium azide generated in situ.
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REFERENCES
M. D. Mashkovskii, Drugs, Vols. 1–2 [in Russian], Novaya Volna, Moscow (2000).
S. J. Wittenberger, Org. Prep. Proced. Int., 26, 499 (1994).
R. N. Butler in: A. R. Katritzky, C. W. Rees, and E. F. V. Scriven (editors), Comprehensive Heterocyclic Chemistry II, Vol. 4, Pergamon Press, Oxford (1996), p. 621.
P. N. Gaponik and V. P. Karavai, Khim. Geterotsikl. Soedin., 1422 (1985).
P. N. Gaponik, V. P. Karavai, and Yu. V. Grigor'ev, Khim. Geterotsikl. Soedin., 1521 (1985).
P. N. Gaponik, V. P. Karavai, I. E. Davshko, M. M. Degtyarik, and A. N. Bogatikov, Khim. Geterotsikl. Soedin., 1528 (1990).
Yu. V. Grigor'ev, I. I. Maruda, and P. N. Gaponik, Izv. Nat. Akad. Nauk Belarus, Ser. Khim. Nauk, No. 4, 86 (1997).
S. V. Voitekhovich, P. N. Gaponik, A. S. Lyakhov, and O. A. Ivashkevich, Pol. J. Chem., 75, 253 (2001).
P. N. Gaponik, S. V. Voitekhovich, I. I. Maruda, A. A. Kulak, and O. A. Ivashkevich, Izv. Nat. Akad. Nauk Belarus, Ser. Khim. Nauk, No. 3, 62 (2001).
V. V. Saraev and E. L. Golod, Zh. Org. Khim., 33, 629 (1997).
P. N. Gaponik, Dissertation for Doctor of Chemical Sciences, Minsk (2000).
T. Schelenz, J. Prakt. Chem., 342, 205 (2000) and literature cited therein.
W. L. Garbrecht and R. M. Herbst, J. Org. Chem., 18, 1014 (1953).
R. Imhof, D. W. Ladner, and J. M. Muchowski, J. Org. Chem., 42, 3709 (1977).
E. Zbiral and W. Schoerkhuber, Liebigs Ann. Chem., 1870 (1982).
F. R. Atherton and R. W. Lambert, Tetrahedron, 39, 2599 (1983).
M. S. Congreve, Synlett, 359 (1996).
R. A. Batey and D. A. Powell, Org. Lett., 2, 3237 (2000).
W. Bocian, J. Jazwinski, W. Kozminski, L. Stefaniak, and G. A. Webb, J. Chem. Soc., Perkin Trans. 2, 1327 (1994).
A. S. Lyakhov, A. N. Vorobiov, P. N. Gaponik, L. S. Ivashkevich, Vad. E. Matulis, and O. A. Ivashkevich, Acta Crystallogr., C59, 690 (2003).
H. H. Capps and W. M. Dehn, J. Am. Chem. Soc., 54, 4301 (1932).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1174–1179, August, 2005.
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Voitekhovich, S.V., Vorob'ev, A.N., Gaponik, P.N. et al. Synthesis of New Functionally Substituted 1-R-tetrazoles and Their 5-Amino Derivatives. Chem Heterocycl Compd 41, 999–1004 (2005). https://doi.org/10.1007/s10593-005-0267-4
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DOI: https://doi.org/10.1007/s10593-005-0267-4