Convenient synthesis of imidazo[1,5-a]pyrimidine derivatives and their unusual recyclization into 3H-imidazo[4,5-b]pyridine derivatives

被引：0
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作者：
Valery S. Tolkunov
Andrew S. Tolkunov
Olga V. Smirnova
Sergei V. Tolkunov
机构：
[1] L. M. Litvinenko Institute of Physical-Organic Chemistry and Coal Chemistry,
来源：
Chemistry of Heterocyclic Compounds | 2021年 / 57卷
关键词：
1,3-diketones; 1; -imidazol-4(5)-amine; imidazo[4,5-; ]pyridines; imidazo[1,5-; ]pyrimidines; trifluoroacetic acid; carbonylation; Dimroth rearrangement;
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摘要：
New derivatives of imidazo[1,5-a]pyrimidine have been synthesized by cyclization of in situ generated 1H-imidazol-4(5)-amine with 1,3-diketones or malondialdehyde derivatives. Utilization of asymmetrical 1,3-diketones leads to the formation of a mixture of regioisomers. The discovered conversion of imidazo[1,5-a]pyrimidine core into 3H-imidazo[4,5-b]pyridine that takes place only under acidic conditions can be considered as a new version of Dimroth rearrangement involving cleavage of C–N bond and formation of C–C bond.
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页码：554 / 559
页数：5
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