Synthesis of highly substituted 2,3-dihydropyrimido[4,5-<Emphasis Type="Italic">d</Emphasis>]pyrimidin-4(1<Emphasis Type="Italic">H</Emphasis>)-ones from 4,6-dichloro-5-formylpyrimidine,amines and aldehydes |
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Authors: | Jinbao Xiang Chao Geng Lang Yi Qun Dang Xu Bai |
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Institution: | (1) The Center for Combinatorial Chemistry and Drug Discovery, The School of Pharmaceutical Sciences and The College of Chemistry, Jilin University, 1266 Fujin Road, Changchun, Jilin, 130021, People’s Republic of China; |
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Abstract: | A practical strategy was developed for the preparation of highly substituted 2,3-dihydropyrimido4,5-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 pyrimido4,5-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-dihydropyrimido4,5-d]pyrimidin-4(1H)-ones in moderate to good yields. |
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