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Heterocycles containing a bridge nitrogen atom. 11. Recyclization of 5-methyloxazolo[3,2-apyridinium cation under the action of nucleophiles containing NH2 group. Crystal structure of 3-(p-nitrophenyl)-1,4-dihydropyrido-[2,1-c]-as-triazinium perchlorate

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Abstract

Reactions of 5-methyl-2-(p-nitrophenyl)oxazolo[3,2-a]pyridinium perchlorate with ammonia and hydrazine, in contrast to the reaction with secondary amines, do not produce indolizines. The reaction with ammonia produces 5-methyl-2-(p-nitrophenyl)imidazo[1,2-a]pyridine; with hydrazine, 3-(p-nitrophenyl)-1,4-dihydropyrido[2,1-c]-as-triazinium semiperchlorate (2 moles of base per one mole of acid). The structure of the latter is solved by X-ray structural studies.

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Authors
  1. E. V. Babaev
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  2. A. V. Efimov
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  3. V. B. Rybakov
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  4. S. G. Zhukov
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Additional information

Dedicated to Professor Henk van der Plas on his 70th birthday.

For No. 9, see [1].

M. V. Lomonosov Moscow State University, Moscow 119899, Russia

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 550–556, April, 1999.

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Babaev, E.V., Efimov, A.V., Rybakov, V.B. et al. Heterocycles containing a bridge nitrogen atom. 11. Recyclization of 5-methyloxazolo[3,2-apyridinium cation under the action of nucleophiles containing NH2 group. Crystal structure of 3-(p-nitrophenyl)-1,4-dihydropyrido-[2,1-c]-as-triazinium perchlorate. Chem Heterocycl Compd 35, 486–491 (1999). https://doi.org/10.1007/BF02319339

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  • DOI: https://doi.org/10.1007/BF02319339

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