Regioselective Synthesis of 3-Arylamino- and 5-Arylaminoisoxazoles from Enaminones

Autor:	Xiaoqing Xin, Xu Liu, Jiming Yang, Dexuan Xiang, Rui Zhang, Dewen Dong
Rok vydání:	2012
Předmět:	Models Molecular Aqueous solution Molecular Structure Organic Chemistry One-pot synthesis Regioselectivity Stereoisomerism Isoxazoles Biochemistry chemistry.chemical_compound Hydroxylamine chemistry Organic chemistry Physical and Theoretical Chemistry Amination
Zdroj:	Organic Letters. 14:644-647
ISSN:	1523-7052 1523-7060
DOI:	10.1021/ol203282h
Popis:	A highly regioselective synthesis of 3-arylamino- and 5-arylaminoisoxazoles from enaminones based on reaction condition selection is reported. 3-Arylaminoisoxazoles were produced by treating enaminones with aqueous hydroxylamine in DMF at 100 °C, whereas 5-arylaminoisoxazoles were synthesized by subjecting enaminones to aqueous hydroxylamine in the presence of KOH and TBAB in water under reflux. A mechanism for the regioselective synthesis of 3-arylamino- and 5-arylaminoisoxazoles is proposed.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::fac053d3f1a43305664e7fc1fc517fbb https://doi.org/10.1021/ol203282h Zobrazit plný text záznamu