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One‐Pot Synthesis of 3,5‐Disubstituted Isoxazoles from Alkynes and Activated Nitroalkanes
Author(s) -
Lin Li,
Zhang Jinlong,
Wang Rui
Publication year - 2012
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201200058
Subject(s) - chemistry , stoichiometry , yield (engineering) , intermolecular force , condensation , combinatorial chemistry , organic chemistry , benzoquinone , medicinal chemistry , molecule , materials science , physics , metallurgy , thermodynamics
The condensation of terminal alkynes and activated nitroalkanes catalyzed by Cu(Ac) 2 ⋅ H 2 O and a stoichiometric amount of 2,3‐dichloro‐5,6‐dicyano‐1,4‐benzoquinone (DDQ) gives 3,5‐disubstituted isoxazoles. Various 3‐carbonyl/ester‐substituted isoxazoles were obtained in yields up to 75 %, and 3‐sulfonylisoxazoles were also obtained in low yield. The reaction is presumed to undergo an oxidative cross‐coupling, then intermolecular cyclization and reduction.