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Volumn 62, Issue 21, 1997, Pages 7201-7204

A reexamination of the mechanism of the Biginelli dihydropyrimidine synthesis. Support for an N-acyliminium ion intermediate

Author keywords

[No Author keywords available]

Indexed keywords

1,2,3,4 TETRAHYDROPYRIMIDINE DERIVATIVE; ACETOACETIC ACID DERIVATIVE; BENZALDEHYDE; IMINE; METHYLUREA; PYRIMIDINE DERIVATIVE;

EID: 0030732273     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971010u     Document Type: Article
Times cited : (505)

References (44)
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