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 Full article

Journal

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

Output data

Year: 2002, Volume: 51, Number: 7, Pages: 1308-1318 Pages count : 11 DOI: 10.1023/A:1020969017314

Tags

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

Authors

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

Affiliations

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
Elibrary:	13405866
OpenAlex:	W2950476183

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Scopus	5
Web of science	6
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