Concise copper-catalyzed one-pot tandem synthesis of benzimidazo[1,2-b]isoquinolin-11-one derivatives

Abstract

A simple and efficient copper-catalyzed one-pot tandem method has been developed for synthesis of benzimidazo[1,2-b]isoquinolin-11-one derivatives via reactions of substituted 2-halo-N-(2-halophenyl)benzamides with alkyl 2-cyanoacetates or malononitrile under mild conditions.

Advances in Copper‐Catalyzed CC Coupling Reactions and Related Domino Reactions Based on Active Methylene Compounds

“…As a result of the intramolecular nucleo-Scheme 20. [60] Rather recently, the same group reported cascade reactions that were based on N-substituted benzamides. Scheme 21.…”

“…On the other hand, when compound 50, which only contained one C À X bond in ring A, was subjected to the re-action with 2-cyano ethyl acetate, coupled compound 51 was provided, whilst substrate 52, which only contained one CÀX bond in ring B, underwent intramolecular CÀO coupling to give compound 53 (Scheme 28). [60] Rather recently, the same group reported cascade reactions that were based on N-substituted benzamides. CuI-catalyzed CÀN coupling reactions with phenylacetonitrile or malonitrile afforded the conversion of N-functionalized obromobenzamides (54) into intermediates 55, which promptly cyclized to form compounds 56.…”

One‐Pot Tandem Synthesis of 2‐Arylbenzoxazole Derivatives via Copper‐Catalyzed CN and CO Bond Formation

“…We recently reported on a copper‐catalyzed one‐pot tandem process for the synthesis of sultam‐fused triazoles 5. In a continuation of this research, we discovered a paper by Fu and co‐workers regarding the reaction of 2‐halo‐ N ‐(2‐haloaryl)benzamide with ethylcyanoacetate or malononitrile to give benzimidazo[1,2‐ b ]isoquinolin‐11‐one derivatives 6. This reaction involves the copper‐catalyzed C ‐arylation of ethylcyanoacetate, followed by the nucleophillic addition of the amide group to the cyano functionality to generate an aminophenylisoquinoline derivative, which further undergoes a C  N coupling reaction to give a benzimidazo[1,2‐ b ]isoquinolin‐11‐one moiety.…”

One-pot three components synthesis of novel 2-iminoquinazolines and 2-imino spiro[indoline-quinazoline/pyrimidine]ones catalyzed by sodium fluoride

“…Quinazolines and their derivatives demonstrated pronounced antibacterial [1,2], anti-inflammatory [3][4][5], antiplasmodial [6][7][8], antitumor [9][10][11], antimicrobial, and antioxidant activities [12,13]. Over the recent years octahydro-quinazolinone derivatives demonstrated potential antibacterial activity against Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa and as calcium antagonist [14].…”