Abstract: Condensation of 16-formyllambertianic acid methyl ester with hippuric acid gave methyl 15,16-epoxy-16-[(4Z)-5-oxo-2-phenyl-4,5-dihydrooxazol-4-ylidenemethyl]labda-8(20),13(16),14-trien-19-oate which underwent ready transformation into 2-benzoylamino-3-(2-furyl)acrylic acid of the labdanoid series. Reactions of the diterpenoid azlactone with amines and alpha-amino acid esters led to the formation of the corresponding carbamoylvinylbenzamides and N-(2-benzoylaminoacryloyl) amino acid esters, and furylacrylic acid hydrazides were formed in reactions with hydrazines. Cyclization of the N'-phenylhydrazide by the action of 1 M aqueous sodium hydroxide gave the corresponding 1,2,4-triazin-6-one. By treatment of the azlactone with aqueous ammonia on heating, 4-substituted 2-phenyl-4,5-dihydroimidazol-5-one was obtained.

Cite: Kharitonov Y.V. , Shul'ts E.E. , Shakirov M.M. , Tolstikov G.A.
Synthetic transformations of higher terpenoids: XV. Transformations of azlactone derived from 16-formyllambertianic acid methyl ester
Russian Journal of Organic Chemistry. 2007. V.43. N6. P.839-851. DOI: 10.1134/S1070428007060073 WOS Scopus РИНЦ

ArticleLinkType.TRANSLATED_TO_ORIGINAL: Харитонов Ю.В. , Шульц Э.Э. , Шакиров М.М. , Толстиков Г.А.
Синтетические трансформации высших терпеноидов. xv. превращения азлактона 16-формилметилламбер-тианата
Журнал органической химии (RUSS J ORG CHEM+). 2007. Т.43. №6. С.843-854. РИНЦ

Dates:

Published print:

Jun 1, 2007

Identifiers:

Web of science	WOS:000248058900007
Scopus	2-s2.0-34547244672
Elibrary	13552999
OpenAlex	W2032157531

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