VI. Synthesis of Heterocyclic Analogs of γ-Aminobutyric Acid from 3,5-Dinitrobenzoic Acid |
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Authors: | Shahkel'dyan I. V. Melekhina E. K. Atroshchenko Yu. M. Efremov Yu. A. Alifanova E. N. Kopyshev M. V. Troitskii N. A. Subbotin V. A. Nikishina M. B. |
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Affiliation: | (1) Tula State Pedagogical Universuty, Tula, 300026, Russia;(2) Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Tula, Russia |
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Abstract: | A series of 7-carboxy-3-R-1,5-dinitro-3-azabicyclo[3.3.1]non-6-enes was synthesized by reduction of 3,5-dinitrobenzoic acid with sodium borohydride followed by Mannich reaction with formaldehyde and primary amines. The mechanism of decomposition under electron impact of the 3-azabicyclo[3.3.1]nonane was established. Enthalpies of formation of compounds synthesized were calculated by semiempirical PM3 method. |
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