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Synthesis of 2‐Aminoquinazoline‐ and 2‐Aminopyrimidine‐Fused Hybrid Scaffolds by Copper‐Catalyzed C( sp 2 )–N Coupling and Cyclization Followed by Oxidation
Author(s) -
Kwak Jung Pyo,
Dao Pham Duy Quang,
Cho Chan Sik
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000427
Subject(s) - chemistry , ceric ammonium nitrate , catalysis , acetonitrile , cyanamide , copper , dimethylformamide , combinatorial chemistry , ammonium nitrate , organic chemistry , medicinal chemistry , polymer , solvent , grafting
2‐(2‐Bromoaryl)‐ and 2‐(2‐bromovinyl)‐4,7‐dimethoxybenzimidazoles are coupled and cyclized with cyanamide as a building block in dimethylformamide in the presence of a catalytic amount of a copper catalyst along with a base to give the corresponding 2‐aminoquinazoline‐ and 2‐aminopyrimidine‐fused 4,7‐dimethoxybenzimidazoles in good yields. Subsequent oxidation of such N‐fused hybrid scaffolds by treatment of ceric ammonium nitrate in acetonitrile/H 2 O affords unprecedented 2‐aminoquinazoline‐ and 2‐aminopyrimidine‐fused benzimidazolequinones.