Issue in Honor of Prof. Vincenzo Tortorella ARKIVOC 2004 (v) 181-195
A general, versatile synthesis of 2H-pyrrolo[3,4-c]quinolines via tosylmethylisocyanide reaction
Roberto Di Santo,* Roberta Costi, Michela Forte, and Carlo Galeffi
Dipartimento di Studi Farmaceutici Università degli Studi di Roma “La Sapienza”, P.le Aldo Moro 5, I-00185 Roma, Italy E-mail: roberto.disanto@uniroma1.it
In honor of Professor Vincenzo Tortorella on the occasion of his "Fuori Ruolo" status (received 14 Dec 03; accepted 02 Mar 04; published on the web 10 Mar 04)
Abstract
A new synthetic procedure for obtaining 2H-pyrrolo[3,4-c]quinolines is reported. The synthetic pathway utilizes TosMIC reaction to prepare appropriate nitroarylpyrrylcarboxylic esters, which on treatment with Fe-AcOH undergo reduction of nitro group with concomitant intramolecular cyclization to give title derivatives. The procedure proved general and more profitable than those previously reported in the literature. The synthesis of still unknown parent compound 4 via TosMIC is described. 2H-Pyrrolo[3,4-c]quinolines substituted at 1 and 3 positions have been obtained by making use of methyl-TosMIC.
Keywords: Pyrroloquinolines, TosMIC, synthesis
Introduction
The presence of heterocyclic structures in many natural and synthetic products endowed with biological activities makes account for the large amount of searches devoted in the past years to the synthesis of novel polycyclic systems containing one or more heteroatoms.
Various 5,6,6 tricyclic pyrrole annulated rings, including pyrroloquinoxalines and pyrroloquinolines, have been used as lead chemical structures for developing chemotherapeutic agents and drugs acting on Central Nervous System. Pyrrolo[1,2-a]quinoxaline parent nucleus and its derivatives have been thoroughly investigated,1 whereas only few reports are available in the literature concerning the synthesis of 2H-pyrrolo[3,4-c]quinoline derivatives.2-4
Our decennial interest in the chemistry of pyrrole annulated heterocyclic systems5-9and our recent involvement in a work project on potential ligands of 5-HT receptors led us to explore new routes for obtaining 2H-pyrrolo[3,4-c]quinoline derivatives.
ISSN 1424-6376 Page 181 ©ARKAT USA, Inc
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