Straightforward Synthesis of Functionalized Furo[3,4-d] pyrimidine-2,4-diones

被引：6

作者：

De Coen, Laurens M. ^{[1
]}

Jatczak, Martyna ^{[1
]}

Muylaert, Koen ^{[1
]}

Mangelinckx, Sven ^{[1
]}

Stevens, Christian V. ^{[1
]}

机构：

[1] Univ Ghent, Dept Sustainable Organ Chem & Technol, Fac Biosci Engn, B-9000 Ghent, Belgium

来源：

SYNTHESIS-STUTTGART | 2015年 / 47卷 / 09期

关键词：

heterocycles; ring closure; alkylation; rearrangement; hydrogenation; MTOR INHIBITORS; CANCER-THERAPY;

D O I：

10.1055/s-0034-1380321

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient synthesis of furo[3,4-d]pyrimidine-2,4-diones has been accomplished via a straightforward three-step pathway. Curtius rearrangement of 4-(methoxycarbonyl)furan-3-carboxylic acid and subsequent reaction with a variety of amines resulted in the corresponding intermediate ureids, which could be ring closed to the bicyclic scaffold in good yields. Functionalization of N-1 afforded a small library of new heterocycles. (Partial) hydrogenation of the furo[3,4-d]pyrimidine- 2,4-diones led to the 5,7-dihydro- and tetrahydrofuro[3,4-d]pyrimidine- 2,4-diones.

引用

页码：1227 / 1237

页数：11

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