Synthesis of tricyclic 4-chloro-pyrimido[4,5-b][1,4]benzodiazepines.
[reaction: see text] A novel methodology was developed for the efficient synthesis of 4-chloro-pyrimido[4,5-b][1,4]benzodiazepines. The key is the intramolecular Friedel-Crafts cyclization of 5-amino-4-(N-substituted)anilino-6-chloropyrimidine with either a carboxylic acid or its derivatives to construct the 4-chloro-pyrimido[4,5-b][1,4]benzodiazepine core. Subsequent nucleophilic substitution allows the introduction of one more diversity point in the target molecules. This strategy provides an efficient method to access a library of compounds based on privileged substructures that are of great interest in drug discovery.
Yang
Jianxin
J
The Center for Combinatorial Chemistry and Drug Discovery, Jilin University, 75 Jinlai Street, Changchun, Jilin 130012, P. R. China.
Che
Xin
X
Dang
Qun
Q
Wei
Zhonglin
Z
Gao
Shu
S
Bai
Xu
X
D001569:Benzodiazepines / Q000138:chemical synthesis*; D002264:Carboxylic Acids / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis*; D015394:Molecular Structure
D002264:Carboxylic Acids; D006576:Heterocyclic Compounds, 4 or More Rings; D001569:Benzodiazepines