Volume 4, Issue 34 p. 10054-10059
Full Paper

Iodine-DMSO-Catalyzed Chemoselective Biomimetic Aromatization of Tetrahydro-β-carbolines-3-carboxylic Acid: Mechanism Study with DFT-Calculation

Sunil V. Gaikwad

Sunil V. Gaikwad

Centre for advance studies, Department of Chemistry, Savitribai Phule Pune University, Ganeshkhind, Pune, 411007 India

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Dinesh N. Nadimetla

Dinesh N. Nadimetla

School of Chemical Science, Goa University, Taleigao Plateau, Goa, 403 206 India

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Dr. Mohammad Al Kobaisi

Dr. Mohammad Al Kobaisi

Department of Chemistry and Biotechnology, FSET, Swinburne University of Technology, Hawthorn VIC, 3122 Australia

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Manisha Devkate

Manisha Devkate

Centre for advance studies, Department of Chemistry, Savitribai Phule Pune University, Ganeshkhind, Pune, 411007 India

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Rekha Joshi

Rekha Joshi

Centre for advance studies, Department of Chemistry, Savitribai Phule Pune University, Ganeshkhind, Pune, 411007 India

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Rohit G. Shinde

Rohit G. Shinde

Centre for advance studies, Department of Chemistry, Savitribai Phule Pune University, Ganeshkhind, Pune, 411007 India

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Milind V. Gaikwad

Milind V. Gaikwad

Department of Chemistry, Dr. D.Y. Patil A. C. S. College, Pimpri, Pune, 411018 India

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Dr. Milind D. Nikalje

Dr. Milind D. Nikalje

Centre for advance studies, Department of Chemistry, Savitribai Phule Pune University, Ganeshkhind, Pune, 411007 India

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Prof. Sheshanath V. Bhosale

Corresponding Author

Prof. Sheshanath V. Bhosale

School of Chemical Science, Goa University, Taleigao Plateau, Goa, 403 206 India

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Prof. Pradeep D. Lokhande

Corresponding Author

Prof. Pradeep D. Lokhande

Centre for advance studies, Department of Chemistry, Savitribai Phule Pune University, Ganeshkhind, Pune, 411007 India

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First published: 11 September 2019
Citations: 8

Graphical Abstract

This paper described a unique I2-DMSO catalyzed chemoselective aromatization of easily accessible THβC-carboxylic acids for the synthesis of β-carboline-3-carboxylic acid. The use of DMSO, I2 is as a HI source and greener solvent. Further, this method can be extended for the aromatization of tetrahydro-β-carboline methyl esters and novel hybrid β-carboline derivatives with excellent yield. The mechanism was supported by DFT calculations.

Abstract

A new protocol for the chemoselective aromatization of tetrahydro-β-carboline-3-carboxylic acids to direct biomimetic one step synthesis of β-carboline-3-carboxylic acids 2 A-L using catalytic amount of I2 in DMSO/H+ produces very good yield. This method was also successfully extended for the aromatization of tetrahydro-β-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.

Conflict of interest

The authors declare no conflict of interest.