Reaction of 5-nitrospiro[benzimidazole-2,1'-cyclohexane] 1,3-dioxide with electrophilic reagents: Bromine and nitric acid Full article
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Russian Journal of Organic Chemistry
ISSN: 1070-4280 , E-ISSN: 1608-3393 |
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| Output data | Year: 2013, Volume: 49, Number: 8, Pages: 1208-1214 Pages count : 7 DOI: 10.1134/S1070428013080198 | ||
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Abstract:
Reactions of 5-nitrospiro[benzimidazole-2,1'-cyclohexane] 1,3-dioxide with bromine and nitric acid lead to the electrophilic substitution of the hydrogen atom in the meta-position with respect to the nitro group. At thebromination the primarily formed 4-bromo-6-nitrospiro[benzimidazole-2,1'-cyclohexane] 1,3-dioxide when kept in the solution loses an oxygen atom forming 4-bromo-6-nitrospiro[benzimidazole-2,1'-cyclohexane] 1-oxide and an isomerization product, 8-bromo-6-nitrospiro[3H-[2,1,4]benzoxadiazine-3,1'-cyclohexane] 4-oxide. The latter exposed to light turns into 4-bromo-6-nitrospiro[benzimidazole-2,1'-cyclohexane] 1,3-dioxide. The reaction of the initial 1,3-dioxide with nitric acid afforded 4,6-dinitrospiro[benzimidazole-2,1'-cyclohexan]-7-ol 1-oxide whose heating in o-dichlorobenzene resulted in 3,5-dinitro-1,8-diazatricyclo[7.5.0.0(2,7)] tetradeca-2(7),3,5,8-tetraen-6-ol.
Cite:
Samsonov V.A.
, Gatilov Y.V.
, Savel'ev V.A.
Reaction of 5-nitrospiro[benzimidazole-2,1'-cyclohexane] 1,3-dioxide with electrophilic reagents: Bromine and nitric acid
Russian Journal of Organic Chemistry. 2013. V.49. N8. P.1208-1214. DOI: 10.1134/S1070428013080198 WOS Scopus РИНЦ OpenAlex
Reaction of 5-nitrospiro[benzimidazole-2,1'-cyclohexane] 1,3-dioxide with electrophilic reagents: Bromine and nitric acid
Russian Journal of Organic Chemistry. 2013. V.49. N8. P.1208-1214. DOI: 10.1134/S1070428013080198 WOS Scopus РИНЦ OpenAlex
Original:
Самсонов В.А.
, Гатилов Ю.В.
, Савельев В.А.
Взаимодействие 5-нитроспиро[бензимидазол-2,1-циклогексан]-1,3-диоксида с электрофильными реагентами - бромом и азотной кислотой
Журнал органической химии (RUSS J ORG CHEM+). 2013. Т.49. №9. С.1223-1229. РИНЦ
Взаимодействие 5-нитроспиро[бензимидазол-2,1-циклогексан]-1,3-диоксида с электрофильными реагентами - бромом и азотной кислотой
Журнал органической химии (RUSS J ORG CHEM+). 2013. Т.49. №9. С.1223-1229. РИНЦ
Dates:
| Published print: | Aug 1, 2013 |
| Published online: | Sep 5, 2013 |
Identifiers:
| Web of science: | WOS:000324112500019 |
| Scopus: | 2-s2.0-84884340982 |
| Elibrary: | 20456576 |
| OpenAlex: | W2156222295 |