SYNTHESIS OF 2,5-PIPERIDINEDIONES - REGIOSELECTIVITY IN THE DIECKMANN CYCLIZATION

被引：11

作者：

BONJOCH, J ^{[1
]}

SERRET, I ^{[1
]}

BOSCH, J ^{[1
]}

机构：

[1] UNIV BARCELONA, FAC PHARM, DEPT ORGAN CHEM, BARCELONA 28, SPAIN

来源：

TETRAHEDRON | 1984年 / 40卷 / 13期

关键词：

D O I：

10.1016/S0040-4020(01)83502-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Dieckmann cyclization of ethyl N-benzyl-N-[(ethoxycarbonyl)methyl] succinamate (2) with sodium ethoxide gave regioselectively .beta.-keto ester 3, whereas when using potassium tert-butoxide or potassium hydride as a base the regioisomer 4 was isolated as the main product. Transesterification of ethyl .beta.-keto esters 3 and 4 with benzyl alcohol followed by hydrogenolysis and decarboxylation of the resulting benzyl esters 5 and 6 led to 1-benzyl-2,5-piperidinedione (1). The preparation of some 4-alkyl- and 4-alkoxycarbonylalkyl derivatives was achieved by alkylation of 5 with the appropriate halide and further hydrogenolysis.

引用

页码：2505 / 2511

页数：7

共 43 条

[1]

BEYERMAN HC, 1959, RECL TRAV CHIM PAY B, V78, P648

[2] 3-PYRROLIDINONES BY INTRAMOLECULAR CONDENSATION [J].