A NEW ACCESS TO PHOSPHAINDOLIZINES BY [3+2] CYCLOADDITION OF AZOMETHINE YLIDES ONTO PHOSPHAALKYNES

被引:39
作者
BERGSTRASSER, U [1 ]
HOFFMANN, A [1 ]
REGITZ, M [1 ]
机构
[1] UNIV KAISERSLAUTERN,FACHBEREICH CHEM,ERWIN SCHRODINGER STASSE,W-6750 KAISERSLAUTERN,GERMANY
关键词
D O I
10.1016/S0040-4039(00)91856-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Azomethine ylides such as 1 and 4 in which the nitrogen atom is incorporated in a six-membered heterocyclic ring undergo regiospecific [3 + 2] cycloadditions with the phosphaalkynes 2a and b at 130-140-degrees-C to furnish the phosphaindolizines 3 and 5a-c after elimination of ethyl formate or hydrogen cyanide, respectively. In contrast, dipoles of the type 6 react unspecifically with the phosphaalkyne 2a to yield the regioisomers 7 and 8.
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页码:1049 / 1052
页数:4
相关论文
共 19 条
[1]   2-PHOSPHAINDOLIZINES [J].
BANSAL, RK ;
KARAGHIOSOFF, K ;
GUPTA, N ;
SCHMIDPETER, A ;
SPINDLER, C .
CHEMISCHE BERICHTE, 1991, 124 (03) :475-480
[2]  
BREIT B, 1992, IN PRESS CHEM BER 53, V125
[3]   UNUSUALLY COORDINATED PHOSPHORUS-COMPOUNDS .24. METHYLIDYNEPHOSPHANE (HC=P), A NEW CYCLO-ADDITION PARTNER FOR 1,3-DIPOLES [J].
FUCHS, EPO ;
HERMESDORF, M ;
SCHNURR, W ;
ROSCH, W ;
HEYDT, H ;
REGITZ, M ;
BINGER, P .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1988, 338 (03) :329-340
[4]   C-METALLIERUNG AN PHOSPHAAROMATEN - 2-LITHIO-1-METHYL-1,3-BENZAZAPHOSPHOL [J].
HEINICKE, J ;
TZSCHACH, A .
TETRAHEDRON LETTERS, 1982, 23 (36) :3643-3646
[5]   SYNTHESIS AND PROPERTIES OF THE 1,3-BENZAZAPHOSPHOLES [J].
ISSLEIB, K ;
VOLLMER, R .
ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE, 1981, 481 (10) :22-32
[6]  
ISSLEIB K, 1978, TETRAHEDRON LETT, V19, P441
[7]   1,3-DIPOLAR CYCLO-ADDITIONS OF 1-CHLORO-2-PHENYL-2-TRIMETHYLSILYL-2-PHOSPHAETHENES WITH AZIDES, NITRILIMINES, NITRILOXIDES AND NITRILYLIDES [J].
MARKL, G ;
TROETSCHSCHALLER, I ;
HOLZL, W .
TETRAHEDRON LETTERS, 1988, 29 (07) :785-788
[9]   4-HYDROXY-1,3-LAMBDA-3-AZAPHOSPHOLE [J].
MARKL, G ;
DORFMEISTER, G .
TETRAHEDRON LETTERS, 1987, 28 (10) :1089-1092
[10]   1-R-1,3-LAMBDA-3-AZAPHOSPHOLE [J].
MARKL, G ;
DORFMEISTER, G .
TETRAHEDRON LETTERS, 1986, 27 (37) :4419-4422