Premium
Haloacetylated enol ethers. 7 . Synthesis of 3‐aryl‐5‐trihalomethylisoxazoles and 3‐aryl‐5‐hydroxy‐5‐trihalomethyl‐4,5‐dihydroisoxazoles
Author(s) -
Martins Marcos A. P.,
Siqueira Geonir M.,
Bastos Giovani P.,
Bonacorso Helio G.,
Zanatta Nilo
Publication year - 1996
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570330612
Subject(s) - chemistry , aryl , hydroxylamine hydrochloride , hydrochloride , hydroxylamine , enol , yield (engineering) , organic chemistry , hydrochloric acid , sulfuric acid , medicinal chemistry , catalysis , alkyl , materials science , metallurgy
β‐Aryl‐β‐methoxyvinyl trihalomethyl ketones 1a‐g, 2a‐g [aryl = p ‐YC 6 H 4 where Y= H, Me, OMe, F, Cl, Br, NO 2 ] are cyclocondensed with hydroxylamine hydrochloride to afford the 3‐aryl‐5‐hydroxy‐5‐trihalomethyl‐4,5‐dihydroisoxazoles 3a‐g, 4a‐f in good yield. The dehydratation of compounds 3a‐g with concentrated sulfuric acid, led the corresponding 3‐aryl‐5‐trichloromethylisoxazoles 5a‐g . An alternative one‐pot procedure yields 3‐aryl‐5‐trihalomethylisoxazoles 5,6a‐g directly by cyclocondesation of 1,2a‐g with hydroxylamine hydrochloride in the presence of an excess of concentrated hydrochloric acid.
Accelerating Research
Robert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom
Address
John Eccles HouseRobert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom