REACTIONS OF 3-CARBOMETHOXY-2-AZA-1,3-BUTADIENE DERIVATIVES WITH DIENOPHILES

被引：16

作者：

BALSAMINI, C ^{[1
]}

BEDINI, A ^{[1
]}

GALARINI, R ^{[1
]}

SPADONI, G ^{[1
]}

TARZIA, G ^{[1
]}

HAMDAN, M ^{[1
]}

机构：

[1] GLAXO RES LABS,I-37100 VERONA,ITALY

来源：

TETRAHEDRON | 1994年 / 50卷 / 43期

关键词：

D O I：

10.1016/S0040-4020(01)89546-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reactions of 1,1-diphenyl-3-carbomethoxy-2-aza-1,3-butadiene derivatives la-e (on C4 : H,H or H,CH3 or H,C6H5, both E and Z isomers), and of the C4 unsubstituted 1-phenyl-1-ethoxy analogue 2, were studied with a number of electron-rich and electron-poor dienophiles, with results showing that la-e give heterocycloadducts in Dlels-Alder reactions with electron-poor dienophiles. Michael adducts were obtained from the EtAlCl(2) catalyzed reactions of these compounds with dimethyl acetylendicarboxylate. Compound 2 gave heterocyclic adducts as well but behaved like a nucleophile, at least in the case of the reactions with dimethyl acetylendicarboxylate and ethyl propynoate: these reactions afforded 2-azatrienes as Michael adducts that gave pyridine derivatives upon heating. The synthesis of the new 1-ethoxy-2-aza-1,3-butadiene 2 is also reported.

引用

页码：12375 / 12394

页数：20

共 41 条

[1] DIELS-ALDER REACTIONS OF AZA-1,3-BUTADIENES AND PHOSPHA-1,3-BUTADIENES WITH ETHYLENE - AN ABINITIO STUDY [J].