Tandem retro-Michael addition-Claisen rearrangement-intramolecular cyclization: One-pot synthesis of densely functionalized ethyl dihydropyrimidine-4-carboxylates from simple building blocks

被引：4

作者：

Naidu, B. Narasimhulu ^{[1
]}

机构：

[1] Bristol Myers Squibb Co, Dept Chem, Wallingford, CT 06492 USA

来源：

SYNLETT | 2008年 / 04期

关键词：

retro-Michael addition; Claisen rearrangement; intramolecular cyclization; 1,6-dihydropyrimidine-4-carboxylates;

D O I：

10.1055/s-2008-1032088

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Pyrolysis of suitably functionalized oxadiazoline diesters in refluxing xylenes provided ethyl 1,2-disubstituted 5-hydroxy-6-oxo-1,6-dihydropyrimidine-4-carboxylates in moderate to good yields. Under thermal conditions, the oxadiazoline esters undergo a sequence of complex molecular reorganizations, namely retro-Michael addition, Claisen rearrangement, and cyclization, to produce the desired pyrimidinones.

引用

页码：547 / 550

页数：4

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