An I2-mediated cascade reaction of 2′-bromoacetophenones with benzohydrazides/benzamides leading to quinazolino[3,2-b]cinnoline or tryptanthrin derivatives?

Organic & Biomolecular Chemistry Pub Date: 2017-01-18 DOI: 10.1039/C6OB02699K

Abstract

An efficient and facile protocol for the synthesis of quinazolinone-fused tetracyclic compounds through an iodine-mediated one-pot cascade reaction of 2′-bromoacetophenones with 2-aminobenzohydrazides or 2-aminobenzamides is reported. With 2-aminobenzohydrazides as the substrates, the reaction gave 5H-quinazolino[3,2-b]cinnoline-7,13-diones in moderate to good yields under metal-catalyst-free conditions. With 2-aminobenzamides as the substrates and CuBr as the catalyst, on the other hand, it afforded tryptanthrin derivatives with good efficiency. Mechanistically, the formation of the tetracyclic systems is initiated by iodination and oxidation of 2′-bromoacetophenones followed by a cascade procedure consisting of cyclocondensation, aromatization and intramolecular cyclization of the in situ formed 2-bromoarylglyoxals with 2-aminobenzohydrazides or 2-aminobenzamides, respectively.

Graphical abstract: An I2-mediated cascade reaction of 2′-bromoacetophenones with benzohydrazides/benzamides leading to quinazolino[3,2-b]cinnoline or tryptanthrin derivatives
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