BENZODIAZEPINE ANALOGS .9. KINETICS AND MECHANISM OF THE AZIDOTRIMETHYLSILANE-MEDIATED SCHMIDT REACTION OF FLAVANONES

被引:11
作者
KAYE, PT
MPHAHLELE, MJ
BROWN, ME
机构
[1] Department of Chemistry, Rhodes University, Grahamstown, 6140
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 | 1995年 / 04期
关键词
D O I
10.1039/p29950000835
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
H-1 NMR spectroscopy has been used to monitor the formation of 1,4-benzoxazepinones and their [1,5-d]tetrazolo analogues via azidotrimethylsilane-mediated Schmidt rearrangement of flavanone precursors. Analysis of the kinetic data has permitted the determination of rate coefficients and rationalization of substituent effects.
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收藏
页码:835 / 838
页数:4
相关论文
共 10 条
[1]   THEORETICAL-STUDY OF THE BARRIER TO NITROGEN INVERSION IN N-CYANOFORMIMINE AND N-DIAZOFORMIMINE - MECHANISM OF THE SCHMIDT REACTION [J].
BACH, RD ;
WOLBER, GJ .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (02) :239-245
[2]   SCHMIDT REACTION WITH AROMATIC KETONES [J].
EVANS, D ;
LOCKHART, IM .
JOURNAL OF THE CHEMICAL SOCIETY, 1965, (SEP) :4806-&
[3]   EFFECTS OF ACID STRENGTH ON SCHMIDT REACTIONS OF ALKYL CYCLOPROPYL KETONES AND ALKYL PHENYL KETONES [J].
FIKES, LE ;
SHECHTER, H .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (05) :741-744
[4]   SYNTHESIS AND STRUCTURE OF 3,4-DIHYDRO-4-PHENYL-1,5-BENZODIOXEPIN-2-ONES [J].
GELEBE, AC ;
KAYE, PT ;
LIDDELL, JR .
SYNTHETIC COMMUNICATIONS, 1991, 21 (22) :2263-2268
[5]   PREPARATION OF SOME 2,3-DIHYDRO-1,4-BENZOXAZEPIN-5(4H)-ONES AND RELATED COMPOUNDS [J].
HUCKLE, D ;
LOCKHART, IM ;
WRIGHT, M .
JOURNAL OF THE CHEMICAL SOCIETY, 1965, (FEB) :1137-&
[6]  
Isaacs N. S., 1987, PHYSICAL ORGANIC CHE, P134
[7]  
KAYE MJ, IN PRESS SYNTH COMMU
[8]  
KAYE PT, 1991, S AFR J CHEM-S-AFR T, V44, P30
[9]  
LITKEI G, 1983, ACTA CHIM HUNG, V114, P47
[10]   THE EFFECT OF STRUCTURE ON THE COURSE OF THE SCHMIDT REACTION ON UNSYMMETRICAL KETONES [J].
SMITH, PAS ;
HORWITZ, JP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1950, 72 (08) :3718-3722