EXPECTED SELECTIVITY AND UNEXPECTED ISOMERIZATION IN THE INVERSE DIELS-ALDER REACTION OF AZOLYL DIENES

被引:14
作者
KOTSCHY, A
HAJOS, G
MESSMER, A
机构
[1] Central Research Institute for Chemistry, Hungarian Academy of Sciences, H-1525 Budapest
关键词
D O I
10.1021/jo00120a041
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Hetaryl-substituted dienamines (la-e and 4a-c) of different geometry when treated with dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate (2) reacted selectively as enamines (i.e. with the Delta 3,4 double bond) to afford the appropriate E or Z (hetarylvinyl)pyridazines (i.e. la-e gave 3a-c, whereas 4a-c afforded 5a-c). Study on the analogous transformation of the 1Z diene ether (6a) revealed that, in apolar solvent, isomerization of the olefinic side chain occurred (3a rather than 5a was obtained). Formation of the trans product 3a was rationalized by a tautomeric equilibrium of the supposed intermediate 7 for which experimental evidence was provided.
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页码:4919 / 4921
页数:3
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