Copper catalyzed access to functionalized oxazoles from oximes via carbenoids

Autor:	K. C. Kumara Swamy, K. Sandeep, Anugula Nagaraju
Rok vydání:	2018
Předmět:	010405 organic chemistry Chemistry Organic Chemistry chemistry.chemical_element One-Step Alcohol 010402 general chemistry 01 natural sciences Biochemistry Copper Medicinal chemistry 0104 chemical sciences Catalysis chemistry.chemical_compound Drug Discovery Molecule Diazo Vicinal Oxazole
Zdroj:	Tetrahedron Letters. 59:2238-2242
ISSN:	0040-4039
DOI:	10.1016/j.tetlet.2018.05.004
Popis:	An operationally simple, economical and straightforward synthesis of diverse oxazoles from oximes possessing a vicinal carbonyl group has been achieved by treatment of the latter with terminal diazo compounds like ethyl/benzyl diazoacetate and diazoacetophenone (which act as carbenoids) in one pot. At least two reducible functional groups (two ester groups or cyano + ester) are simultaneously introduced in one step. This reaction involves expulsion of a molecule each of N 2 and water only as byproducts under copper catalysis. The structure of one of these oxazoles is confirmed by X-ray crystallography. Both the ester groups in the oxazole product could be reduced to alcohol moieties by using NaBH 4 /EtOH.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::79f8324f47934500fe9b3aa6bead4b62 https://doi.org/10.1016/j.tetlet.2018.05.004 Zobrazit plný text záznamu Full Text from ScienceDirect