HYPERVALENT IODINE OXIDATION OF N-ACYLHYDRAZONES AND N-PHENYLSEMICARBAZONE - AN EFFICIENT METHOD FOR THE SYNTHESIS OF DERIVATIVES OF 1,3,4-OXADIAZOLES AND DELTA(3)-1,3,4-OXADIAZOLINES

Authors
YANG RY DAI LX
Citation
Ry. Yang et Lx. Dai, HYPERVALENT IODINE OXIDATION OF N-ACYLHYDRAZONES AND N-PHENYLSEMICARBAZONE - AN EFFICIENT METHOD FOR THE SYNTHESIS OF DERIVATIVES OF 1,3,4-OXADIAZOLES AND DELTA(3)-1,3,4-OXADIAZOLINES, Journal of organic chemistry, 58(12), 1993, pp. 3381-3383
Citations number
38
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
58
Issue
12
Year of publication
1993
Pages
3381 - 3383
Database
ISI
SICI code
0022-3263(1993)58:12<3381:HIOONA>2.0.ZU;2-N
Abstract
The oxidation of ketone N-acylhydrazones 1 by phenyliodine(III) diacet ate (PIDA) in alcohol gave 2-alkoxy-DELTA3-1,3,4-oxadiazolines 4 in ex cellent yields, while the oxidative cyclization of aldehyde N-acylhydr azone 2 by PIDA in methanolic sodium acetate gave 2,5-disubstituted 1, 3,4-oxadiazoles in good yields. The oxidation of acetone 4-phenylsemic arbazone afforded 2-(N-phenylimino)-DELTA3-1,3,4-oxadiazoline in excel lent yield.