Synthesis of highly substituted 2,3-dihydropyrimido[4,5-d]pyrimidin-4(1H)-ones from 4,6-dichloro-5-formylpyrimidine, amines and aldehydes

被引：12
|
作者：
Xiang, Jinbao [1 ,2 ]
Geng, Chao [1 ,2 ]
Yi, Lang [1 ,2 ]
Dang, Qun [1 ,2 ]
Bai, Xu [1 ,2 ]
机构：
[1] Jilin Univ, Ctr Combinatorial Chem & Drug Discovery, Sch Pharmaceut Sci, Changchun 130021, Jilin, Peoples R China
[2] Jilin Univ, Coll Chem, Changchun 130021, Jilin, Peoples R China
来源：
MOLECULAR DIVERSITY | 2011年 / 15卷 / 04期
基金：
中国国家自然科学基金;
关键词：
2,3-dihydropyrimido[4,5-d]pyrimidin-4(1H)-ones; 4,6-dichloro-5-formylpyrimidine; Cyclization reaction; Intramolecular amide addition; TANDEM IMINIUM CYCLIZATION; SMILES REARRANGEMENT; CASCADE REACTION; ION CYCLIZATION; DESIGN; INHIBITORS; DIHYDROPTERIDINES; HETEROCYCLES; DERIVATIVES; LIBRARY;
D O I：
10.1007/s11030-011-9314-5
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
A practical strategy was developed for the preparation of highly substituted 2,3-dihydropyrimido[4,5-d]pyrimidin-4(1H)-ones from 4,6-dichloro-5-formylpyrimidine, primary amines, and aldehydes. The key step for this synthesis entails a cyclization reaction involving an intramolecular amide addition to an iminium intermediate formed in situ from 4-amino-pyrimidine-5-carboxamide 2 and aldehydes to form the pyrimido[4,5-d]pyrimidine core with a strategically placed 5-Cl group for further derivatization. The utility of this methodology was demonstrated through the preparation of a 27-membered library of representative 2,3-dihydropyrimido[4,5-d]pyrimidin-4(1H)-ones in moderate to good yields.
引用
收藏
页码：839 / 847
页数：9
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