A simple and efficient method for the synthesis of 5,6-dihydropyrazin-2(1H)-one O-(tert-butyl)oximes, quinoxalin-2(1H)-one O-(tert-butyl)oximes and its derivatives

Autor:	Tadashi Aoyama, Mamiko Hayakawa, Akihiko Ouchi, Shigeru Shimada, Kenshiro Tashiro
Rok vydání:	2018
Předmět:	Tert butyl chemistry.chemical_classification Double bond 010405 organic chemistry Chemistry Organic Chemistry Intramolecular cyclization 010402 general chemistry 01 natural sciences Biochemistry Medicinal chemistry 0104 chemical sciences chemistry.chemical_compound Bromide Drug Discovery
Zdroj:	Tetrahedron Letters. 59:4116-4119
ISSN:	0040-4039
DOI:	10.1016/j.tetlet.2018.10.015
Popis:	A simple and efficient method was developed for the synthesis of 5,6-dihydropyrazin-2(1H)-one O-(tert-butyl)oximes, quinoxalin-2(1H)-one O-(tert-butyl)oximes and its derivatives from N-tert-butoxy acyl imidoyl bromide and diamines. Twenty three novel compounds were readily synthesized using this procedure in excellent yields. The products possessed Z-stereochemistry with regard to the C N double bond. In these reactions, the amino group first attacked an imidoyl carbon of the N-tert-butoxy acyl imidoyl bromide in order to obtain the Z-intermediate; then another amino group attacked the carbonyl carbon of the intermediate. The rate of intramolecular cyclization of the intermediate was dependent on the position of the diamino groups.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::96bf4f7a3d4b0024e70f3cd47cf1f70f https://doi.org/10.1016/j.tetlet.2018.10.015 Zobrazit plný text záznamu Full Text from ScienceDirect