Synthesis of novel 8,9-dihydro-5H-pyrimido[4,5-e][1,4]diazepin-7(6H)-ones.
Practical and efficient methods have been developed for the synthesis of 4,6,8,9-tetrasubstituted 8,9-dihydro-5H-pyrimido[4,5-e][1,4]diazepin-7(6H)-ones from 4,6-dicholoropyrimidine aldehyde, N-substituted amino acid esters, and amines in five steps. This synthetic strategy is based on suitably substituted pyrimidines as bis-electrophilic species reacting with various amines to construct the pyrimido[4,5-e][1,4]diazepine core with a strategically anchored functional group for further derivatization. The utility of this methodology was demonstrated through the preparation of a 33-membered library of representative 8,9-dihydro-5H-pyrimido[4,5-e][1,4]diazepin-7(6H)-ones in good to excellent yields.
Xiang
Jinbao
J
The Center for Combinatorial Chemistry and Drug Discovery, The School of Pharmaceutical Sciences and The College of Chemistry, Jilin University, Changchun, Jilin, PR China.
Wen
Dongsheng
D
Xie
Hongxiang
H
Dang
Qun
Q
Bai
Xu
X
D000447:Aldehydes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D000596:Amino Acids / Q000737:chemistry*; D001381:Azepines / Q000138:chemical synthesis* / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D004952:Esters / Q000737:chemistry*; D015394:Molecular Structure; D011743:Pyrimidines / Q000138:chemical synthesis* / Q000737:chemistry; D054852:Small Molecule Libraries; D013237:Stereoisomerism
D000447:Aldehydes; D000588:Amines; D000596:Amino Acids; D001381:Azepines; D004952:Esters; D011743:Pyrimidines; D054852:Small Molecule Libraries