Reactions of 5-Nitrospiro[benzimidazole-2,1 '-cyclohexane] 1,3-Dioxide with Nucleophiles

Reactions of 5-Nitrospiro[benzimidazole-2,1 '-cyclohexane] 1,3-Dioxide with Nucleophiles Full article

Journal

Russian Journal of Organic Chemistry
ISSN: 1070-4280 , E-ISSN: 1608-3393

Output data

Year: 2012, Volume: 48, Number: 3, Pages: 399-410 Pages count : 12 DOI: 10.1134/S1070428012030116

Authors

Samsonov V.A. ¹ , Gatilov Yu.V. ¹ , Savel'ev V.A. ¹ , Baranova S.S. ¹

Affiliations

1	(Данные Web of science) Russian Acad Sci, Siberian Div, Vorozhtsov Novosibirsk Inst Organ Chem, Novosibirsk 630090, Russia

Reactions of 5-nitrospiro[benzimidazole-2,1'-cyclohexane] 1,3-dioxide with aliphatic amines and sodium hydroxide resulted in removal of one N-oxide oxygen atom and formation of 4-alkylamino- or 4-hydroxy-substituted 5-nitrospiro[benzimidazole-2,1'-cyclohexane] 1-oxides, respectively. The title compound reacted with ammonia and methylamine in the presence of MnO2 with conservation of both N-oxide moieties, and the products were 4-amino- and 4-methylamino-5-nitrospiro[benzimidazole-2,1'-cyclohexane] 1,3-dioxides. The reactions with aromatic amines were accompanied by removal of both N-oxide oxygen atoms with formation of N-aryl-5-nitrospiro[benzimidazole-2,1'-cyclohexane]-4-amines. In the reactions of 5-nitrospiro[ benzimidazole-2,1'-cyclohexane] 1,3-dioxide with sodium azide and aromatic amine hydrochlorides nucleophilic replacement of the 5-nitro group by azido or arylamino occurred, in the first case both N-oxide fragments being conserved. The reactions with aromatic amine hydrochlorides afforded N-aryl-5-nitrospiro[benzimidazole-2,1'-cyclohexan]-4-amine 1-oxides. Treatment of 5-nitrospiro[benzimidazole-2,1'-cyclohexane] 1,3-dioxide with sodium cyanide led to the formation of 5-oxo-3,5-dihydrospiro[benzimidazole-2,1'-cyclohexane]-4-carbonitrile 1-oxide.

Samsonov V.A. , Gatilov Y.V. , Savel'ev V.A. , Baranova S.S.
Reactions of 5-Nitrospiro[benzimidazole-2,1 '-cyclohexane] 1,3-Dioxide with Nucleophiles
Russian Journal of Organic Chemistry. 2012. V.48. N3. P.399-410. DOI: 10.1134/S1070428012030116 WOS Scopus РИНЦ

Самсонов В.А. , Гатилов Ю.В. , Савельев В.А. , Баранова С.С.
Взаимодействие 5-нитроспиро[бензимидазол-2,1-циклогексан]- 1,3-диоксида с нуклеофильными реагентами
Журнал органической химии (RUSS J ORG CHEM+). 2012. Т.28. №3. С.403-413. РИНЦ

Самсонов В.А. , Гатилов Ю.В. , Савельев В.А. , Баранова С.С.
Кислотно-катализируемые превращения терпеноидов пинаиового ряда. новые возможности
Журнал органической химии (RUSS J ORG CHEM+). 2008. Т.44. №1. С.11-31. РИНЦ

Published print:	Mar 1, 2012
Published online:	Apr 5, 2012

Web of science	WOS:000303682700011
Scopus	2-s2.0-84859561151
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