Synthesis of pyrroles from 1-dialkylamino-3-phosphoryl(or phosphanyl)allenes through 1,5-cyclization of conjugated azomethine ylide intermediates

被引:63
作者
Reisser, M [1 ]
Maas, G [1 ]
机构
[1] Univ Ulm, Div Organ Chem 1, D-89081 Ulm, Germany
关键词
D O I
10.1021/jo049586o
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
1-Dialkylamino-1,3-diaryl-3-diphenylphosphanylallenes 3a-e are thermally converted into a-annulated 3,5-diarylpyrroles 6a-f and [a] -annulated benzo[c]azepines 7a,b,d. These transformations are likely to include conjugated azomethine ylide intermediates that can undergo either a 1,5- or a 1,7-electrocyclization. The periselectivity is markedly shifted toward 1,5-cyclization when the diphenylphosphanyl substituent is replaced by the diphenylphosphoryl group. Thus, 1-dialkylamino-3-(diphenylphosphoryl)allenes 4a-f yield pyrroles 6 exclusively and with improved yields, unless the 3-aryl substituent in the allene is too electron-rich (e.g., benzodioxol-5-yl, 4f --> 7f). The preparation and thermal transformation of aminoallenes 4 over three or four steps can be conducted as a one-pot procedure, thus providing a convenient synthesis of [a]-annulated 3,5-diarylpyrroles from enaminoketones.
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页码:4913 / 4924
页数:12
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