Copper‐Promoted Tandem Three‐Component Access to Quinazolin‐4(H)‐imines and Benzimidazo[1,2‐c]quinazolines

A copper‐catalyzed three‐component assembly of cyanamides, 2‐cyanoarylboronic acids and amines has been developed, providing functionalized quinazolin‐4(H)‐imines. Subsequent access to benzimidazo[1,2‐c]quinazolines is achieved building again on copper‐catalysis. One pot hydrolysis of quinazolin‐4(H...

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Veröffentlicht in:Advanced synthesis & catalysis 2019-10, Vol.361 (19), p.4454-4460
Hauptverfasser: Rodrigues, Romain, Tran, Lam Quang, Darses, Benjamin, Dauban, Philippe, Neuville, Luc
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Sprache:eng
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Zusammenfassung:A copper‐catalyzed three‐component assembly of cyanamides, 2‐cyanoarylboronic acids and amines has been developed, providing functionalized quinazolin‐4(H)‐imines. Subsequent access to benzimidazo[1,2‐c]quinazolines is achieved building again on copper‐catalysis. One pot hydrolysis of quinazolin‐4(H)‐imines to quinazolin‐4(3H)‐ones is also described. Guanidine formation, cyclization and intramolecular C−H bond amination are key features of the process fully mediated by copper.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201900658