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

作者：Guo, Shenghai^*; Zhai, Jianhui; Fan, Xuesen^*

来源：Organic and Biomolecular Chemistry, 2017, 15(6): 1521-1529.

DOI：10.1039/c6ob02699k

• INTRAMOLECULAR N-ARYLATION
• IODINE-CATALYZED SYNTHESIS
• ARYL METHYL KETONES
• ONE-POT SYNTHESIS
• ACRIDONE ALKALOIDS
• AQUEOUS AMMONIA
• TANDEM REACTION
• REGIOSELECTIVE SYNTHESIS
• QUINAZOLINONE ALKALOIDS
• 2-FORMYLBENZOIC ACIDS

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.

• 出版日期2017-2-14
• 单位河南师范大学