Iodine-DMSO-catalyzed chemoselective biomimetic aromatization of tetrahydro-beta-carbolines-3-carboxylic Acid: Mechanism study with DFT-calculation

Gaikwad, S.V.; Nadimetla, D.N.; Kobaisi, M.A.; Devkate, M.; Joshi, R.; Shinde, R.G.; Gaikwad, M.V.; Nikalje, M.D.; Bhosale, S.V.; Lokhande, P.D.

Iodine-DMSO-catalyzed chemoselective biomimetic aromatization of tetrahydro-beta-carbolines-3-carboxylic Acid: Mechanism study with DFT-calculation

Gaikwad, S.V.; Nadimetla, D.N.; Kobaisi, M.A.; Devkate, M.; Joshi, R.; Shinde, R.G.; Gaikwad, M.V.; Nikalje, M.D.; Bhosale, S.V.; Lokhande, P.D.

Source : ChemistrySelect. 4(34); 2019; 10054-10059.

URI: https://doi.org/10.1002/slct.201902419
http://irgu.unigoa.ac.in/drs/handle/unigoa/5851

Date: 2019

Document Type: Journal article

Abstract:

A new protocol for the chemoselective aromatization of tetrahydro-beta-carboline-3-carboxylic acids to direct biomimetic one step synthesis of beta-carboline-3-carboxylic acids 2 A-L using catalytic amount of I sub(2) in DMSO/H sup(+) produces very good yield. This method was also successfully extended for the aromatization of tetrahydro-beta-carboline-3-methyl esters 5 A-G as well as one-step synthesis of Marinacarbolines-D analog, respectively. Further, the mechanism and role of iodine-DMSO in aromatization has been studied by Density Functional Theory Calculation.

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