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Reactions of 3-carene, limonene, and alpha-pinene nitrosochlorides with imidazole, benzotriazole, and indole Full article

Journal Russian Chemical Bulletin
ISSN: 1066-5285 , E-ISSN: 1573-9171
Output data Year: 2012, Volume: 61, Number: 3, Pages: 589-595 Pages count : DOI: 10.1007/s11172-012-0085-7
Tags monoterpenoids; 3-carene; alpha-pinene; limonene; alpha-amino-oxime; imidazole; benzotriazole; indole; nitroso olefin
Authors Bizyaev S. N. 1 , Tkachev A. V. 1,2
Affiliations
1 (Данные Web of science) Russian Acad Sci, Siberian Branch, NN Vorozhtsov Inst Organ Chem, Novosibirsk 630090, Russia
2 (Данные Web of science) Novosibirsk State Univ, Dept Nat Sci, Novosibirsk 630090, Russia

Abstract: The reactions of terpene nitrosochlorides derived from 3-carene, alpha-pinene, and limonene, with simplest azaheterocycles (imidazole, benzotriazole, and indole) were studied. On the base of these transformations, preparative procedures to access chiral oximes bearing azaheterocyclic moieties in the alpha-position to the oxime fragment, namely, alpha-(1H-imidazol-1-yl)-, alpha-(1H-benzo-[d][1,2,3]triazol-1-yl)-, and alpha-(1H-indol-3-yl)-substituted terpenic oximes, were developed. Transformations of the studied monoterpene nitrosochlorides into alpha-substituted oximes proceeded stereoselectively to give in the moderate yields (30-60%) the only stereoisomer arising from the attack of the heterocyclic anion from the less hindered side of the intermediate nitroso olefin generated in situ from nitrosochloride.
Cite: Bizyaev S.N. , Tkachev A.V.
Reactions of 3-carene, limonene, and alpha-pinene nitrosochlorides with imidazole, benzotriazole, and indole
Russian Chemical Bulletin. 2012. V.61. N3. P.589-595. DOI: 10.1007/s11172-012-0085-7 WOS Scopus РИНЦ OpenAlex
Original: Бизяев С.Н. , Ткачев А.В.
Реакция нитрозохлоридов 3-карена, лимонена и α-пинена с имидазолом, бензотриазолом и индолом
Известия Академии наук. Серия химическая.(RUSS CHEM B+). 2012. №3. С.587-593. РИНЦ
Dates:
Published print: Mar 1, 2012
Published online: Dec 16, 2012
Identifiers:
Web of science: WOS:000312494700013
Scopus: 2-s2.0-84875724154
Elibrary: 20475390
OpenAlex: W2095042062
Citing:
DB Citing
Web of science 10
Scopus 9
Elibrary 8
OpenAlex 8
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