A Cascade Reaction with Iminium Ion Isomerization as the Key Step Leading to Tetrahydropyrimido[4,5-d]pyrimidines

A novel cascade reaction of aminopyrimidines 1 with N-alkyl amino acids or analogues was investigated. The keys to this cascade are the isomerization of an iminium ion formed between the aldehyde group in pyrimidine and the secondary amine of an amino acid, and subsequent cyclization to the neighbor...

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Bibliographic Details
Published in:Organic letters 2008-03, Vol.10 (5), p.889-892
Main Authors: Zheng, Lianyou, Yang, Fengzhi, Dang, Qun, Bai, Xu
Format: Article
Language:English
Subjects:
Crystallography, X-Ray
Imines - chemistry
Molecular Conformation
Molecular Structure
Oxidation-Reduction
Pyrimidines - chemical synthesis
Pyrimidines - chemistry
Stereoisomerism
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Summary:A novel cascade reaction of aminopyrimidines 1 with N-alkyl amino acids or analogues was investigated. The keys to this cascade are the isomerization of an iminium ion formed between the aldehyde group in pyrimidine and the secondary amine of an amino acid, and subsequent cyclization to the neighboring amino group. This sequence could be useful in the synthesis of novel tetrahydropyrimido[4,5-d]pyrimidine libraries.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol703049j