4.4 Article

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

Journal

CHEMISTRYSELECT
Volume 4, Issue 34, Pages 10054-10059

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/slct.201902419

Keywords

Aromatization; DFT; DMSO; Iodine; Marine-beta-carboline alkaloids

Funding

  1. UGC-BSR, UGC-New Delhi [F.4-3/2006(BSR)]
  2. EUPHRATES, an Erasmus Mundus Lot 13 project (Europe, India) [2013-2540/001-001]
  3. Council of Scientific & Industrial Research (CSIR), India [02(0357)/19/EMR-II]
  4. UGC
  5. University Grant Commission (UGC) Faculty Research Program, New Delhi, India

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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-2 in DMSO/H+ 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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