Synthesis of indolo- and benzothieno[3,2-c]quinolines via POCl₃ mediated tandem cyclization of o-alkynylisocyanobenzenes derived from o-alkynyl-N-phenylformamides

Abstract

A synthesis of indolo[3,2-c]quinolines and benzothieno[3,2-c]quinolines has been developed employing o-alkynyl-N-phenylformamide derivatives as the substrates. The reaction proceeded via a tandem process involving POCl3‒assisted intramolecular cyclization of the firstly formed...

One-pot access to 11-methyl-6H-indolo[2,3-b]quinolines via iodine-mediated annulation of indoles with 2-vinylanilines and evaluation of their biological activities

“…Besides, the incorporation of chloro-and bromo-moieties in indolo[2,3-b]quinolines made them synthetically attractive for further structural modification. 18 Considering the significance of DiMIQ as both an antibacterial and cytotoxic agent, we were particularly intrigued by the possibility of synthesizing it using our newly developed method (Scheme 4). Accordingly, a scaled-up synthesis of 3a a Reaction conditions: 1 (0.4 mmol), 2 (0.2 mmol) and iodine in solvent (2.0 mL) stirred under air for 12 h. b Isolated yield.…”

“…Besides, the incorporation of chloro- and bromo-moieties in indolo[2,3- b ]quinolines made them synthetically attractive for further structural modification. 18…”