Synthesis of functionalized pyrimidine-4-thiones and derivatives of pyrido[2,3-d]pirimidine-5-one from monoacylketene aminals
Dorokhov, V. A. ; Komkov, A. V. ; Shashkova, E. M. ; Bogdanov, V. S. ; Bochkareva, M. N.
Springer
Published 1993
Springer
Published 1993
| ISSN: |
1573-9171
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|---|---|
| Keywords: |
monoacylketene aminals ; benzoyl isothiocyanate ; heterocyclization ; pyrimidine-4-thiones ; pyrido[2,3-d]pyrimidine-5-ones ; dimethylformamide dimethylacetal
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| Source: |
Springer Online Journal Archives 1860-2000
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| Topics: |
Chemistry and Pharmacology
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| Notes: |
Abstract Monoacylketene aminals containing an unsubstituted NH2 group react as C-nucleophiles with benzoyl isothiocyanate to give the corresponding thioamides which undergo cyclization by sodium methoxide in methanol to afford 6-R-amino-5-acetyl-2-phenyl-3H-pyrimidine-4-thiones. A scheme for constructing the pyrido[2,3-d]pyrimidine system from keteneaminals is offered. The reaction of 6-R-amino-5-acetyl-2-phenyl-3H-pyrimidine-4-thiones with dimethylformamide dimethylacetal leads to 8-R-N-4-methylthio-8H-pyrido-[2,3-d]pyrimidine-5-ones. Cyclization of 5-acetyl-6-benzoylamino-4-methylthio-2-phenylpyrimidine by sodium methoxide yields N-unsubstituted 4-methylthio-8H-pyrido-[2,3-d]pyrimidine-5-one.
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| Type of Medium: |
Electronic Resource
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| URL: |