期刊
MOLECULAR DIVERSITY
卷 16, 期 4, 页码 639-649出版社
SPRINGER
DOI: 10.1007/s11030-012-9398-6
关键词
Pyrido[2,3-d]pyrimidin-7(8H)-ones; Arylguanidines; 3-Aryl-3,4,5,6-tetrahydropyrido[2,3d]pyrimidin-7( 8H)-ones; Dimroth rearrangement
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资金
- IQS
A practical protocol was developed for the synthesis of 2-arylamino substituted 4-amino-5,6-dihydropyrido[2,3-d]pyrimidin-7(8H)-ones from alpha,beta-unsaturated esters, malononitrile, and an aryl substituted guanidine via the corresponding 3-aryl-3,4,5,6- tetrahydropyrido[2,3-d]pyrimidin-7(8H)-ones. Such compounds are formed upon treatment of 2-methoxy-6-oxo-1,4,5,6-tetrahydropyridine-3-carbonitriles with an aryl substituted guanidine in 1,4-dioxane and are converted to the desired 4-aminopyridopyrimidines with NaOMe/MeOH through a Dimroth rearrangement. The overall yields of this three-step protocol are, generally speaking, higher than the multicomponent reaction, previously developed by our group, between an alpha,beta-unsaturated ester, malononitrile, and an aryl substituted guanidine.
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