The preparation of 4,5-dihydro-5-phenyl-5-(2-phenylethenyl)isoxazoles, 4,5-dihydro-5-methyl-5-(2-phenylethenyl)isoxazoles, or 4,5-dihydro-5,5-di(2-phenylethenyl)isoxazoles from dilithiated c(alpha),O-oximes and select alpha,beta-unsaturated ketones

Authors
Townsend, JD Kelley, W Rose, KL Schady, DA Downs, JR Greer, HA Pastine, SJ Beam, CF
Citation
Jd. Townsend et al., The preparation of 4,5-dihydro-5-phenyl-5-(2-phenylethenyl)isoxazoles, 4,5-dihydro-5-methyl-5-(2-phenylethenyl)isoxazoles, or 4,5-dihydro-5,5-di(2-phenylethenyl)isoxazoles from dilithiated c(alpha),O-oximes and select alpha,beta-unsaturated ketones, SYN COMMUN, 30(12), 2000, pp. 2175-2189
Citations number
42
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNTHETIC COMMUNICATIONS
ISSN journal
00397911 → ACNP
Volume
30
Issue
12
Year of publication
2000
Pages
2175 - 2189
Database
ISI
SICI code
0039-7911(2000)30:12<2175:TPO44>2.0.ZU;2-P
Abstract
C(alpha),O-oximes were dilithiated with lithium diisopropylamide and conden sed with three a,P-unsaturated ketones: (2E)-1,3-diphenyl-2-propen-1-one, o r (1E, 4E)-1,5-diphenyl-1,4-pentadien-3-one, or (3E)-4-phenyl-3-buten-2-one , followed by immediate acid cyclization to variously substituted 4,5-dihyd ro-isoxazoles: 4,5-dihydro-5-phenyl-5-(2-phenylethenyl) 4,5-dihydro-5-methy l-5-(2-phenylethenyl)isoxazoles, or 4,5-dihydro-5,5-di-(2-phenylethenyl)iso xazoles.