Synthesis of indole-containing analogs of (1R)-cis-chrysanthemic acid and N-substituted (1R)-cis-chrysanthemylamines

Synthesis of indole-containing analogs of (1R)-cis-chrysanthemic acid and N-substituted (1R)-cis-chrysanthemylamines Научная публикация

Журнал

Russian Chemical Bulletin
ISSN: 1066-5285 , E-ISSN: 1573-9171

Вых. Данные

Год: 2002, Том: 51, Номер: 7, Страницы: 1308-1318 Страниц : 11 DOI: 10.1023/A:1020969017314

Ключевые слова

(+)-car-3-ene; amides; Cyclopropane methyl ketones; Decyanation; Epimerization; Fischer indole synthesis; Hydrolysis; Indolic analogs of chrysanthemylamine; N-cyanamides; Nitriles; Racemization; Reduction

Авторы

Burchak O.N. ¹ , Chibiryaev A.M. ^1,2 , Tkachev A.V. ^1,2

Организации

1	(Scopus) N. N. Vorozhtsov Novosibirsk I., Siberian Br. the Russ. Acad. of Sci., 9 prosp. Akad. Lavrent'eva, 630090 Novosibirsk, Russian Federation
2	(Scopus) Department of Natural Sciences, Novosibirsk State University, 2 ul. Pirogova, 630090 Novosibirsk, Russian Federation

The indolic analogs of (1R)-cis-chrysanthemic acid and N-substituted (1R)-cis-chrysanthemylamines were obtained by Fischer indole synthesis using the acetonylcyclopropanes derived from (+)-car-3-ene. The cyano- and N-cyanamido groups in the starting carbonyl compounds did not hinder indolization. The reduction of the nitrile group bound to the asymmetrical atom of the cyclopropane ring by LiAlH4 in ether can be accompanied by epimerization or racemization.

Burchak O.N. , Chibiryaev A.M. , Tkachev A.V.
Synthesis of indole-containing analogs of (1R)-cis-chrysanthemic acid and N-substituted (1R)-cis-chrysanthemylamines
Russian Chemical Bulletin. 2002. V.51. N7. P.1308-1318. DOI: 10.1023/A:1020969017314 WOS Scopus РИНЦ OpenAlex

Web of science:	WOS:000179423500030
Scopus:	2-s2.0-0141610582
РИНЦ:	13405866
OpenAlex:	W2950476183

БД	Цитирований
Scopus	5
Web of science	6
РИНЦ	5
OpenAlex	5