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

ArticleLinkType.TRANSLATED_TO_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

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