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Iodine‐DMSO‐Catalyzed Chemoselective Biomimetic Aromatization of Tetrahydro‐ β ‐carbolines‐3‐carboxylic Acid: Mechanism Study with DFT‐Calculation
Author(s) -
Gaikwad Sunil V.,
Nadimetla Dinesh N.,
Kobaisi Mohammad Al,
Devkate Manisha,
Joshi Rekha,
Shinde Rohit G.,
Gaikwad Milind V.,
Nikalje Milind D.,
Bhosale Sheshanath V.,
Lokhande Pradeep D.
Publication year - 2019
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201902419
Subject(s) - aromatization , chemistry , yield (engineering) , catalysis , carboxylic acid , iodine , mechanism (biology) , density functional theory , reaction mechanism , combinatorial chemistry , organic chemistry , computational chemistry , materials science , philosophy , epistemology , metallurgy
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 I 2 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.