CONVENIENT PREPARATIONS OF DIETHYL [(ACYLAMINO)METHYL]PHOSPHONATES, 2-AZABUTADIENES, AND ISOQUINOLINES FROM A 1,2-MONOAZABISYLIDE EQUIVALENT

被引:18
作者
KATRITZKY, AR
ZHANG, GF
JIANG, JL
机构
[1] Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville
关键词
D O I
10.1021/jo00095a035
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Diethyl [(triphenylphosphoranylidene)amino]methyl]phosphonate (4), prepared in situ by treatment of 1-[[(triphenylphosphoranylidene)amino]methyl]benzotriazole (betmip 6) with diethyl phosphite anion,is converted by treatment with butyllithium into the corresponding carbanion 5. Carbanion 5, the first example of a 1,2-monoazabisylide equivalent, provides a versatile synthetic method to introduce the C=NC=C structural unit, as illustrated by convenient preparations of 1,4-diaryl-2-azabutadienes, 1,1,4,4-tetraaryl-2-azabutadienes, diethyl [(acylamino)methyl]phosphonates, and isoquinolines.
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页码:4556 / 4560
页数:5
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