Reactions of 3-carene, limonene, and alpha-pinene nitrosochlorides with imidazole, benzotriazole, and indole Full article
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Russian Chemical Bulletin
ISSN: 1066-5285 , E-ISSN: 1573-9171 |
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| 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 | ||||
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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
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
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 |