Synthesis of bis(indolyl)methanes Catalyzed by Triethylborane

Author(s): J. Pablo Garcia Merinos , Heraclio Lopez Ruiz , Yliana Lopez , Susana Rojas .

Journal Name: Letters in Organic Chemistry

Volume 12 , Issue 5 , 2015

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Abstract:

Triethylborane (TEB) was found to be a mild, efficient, and acid catalyst in electrophilic substitution reaction of indoles with aldehydes compounds to afford the corresponding bis(indolyl)methanes. Vibrindole A (5) and bis(indolyl)methanes derivatives 16 and 18 were synthesized using this methodology. Compound 16 is an intermediary in the synthesis of the natural bisindoles arsindoline B (2) and streptindole (6). The structure of vibrindole A (5) was unequivocally confirmed by a single crystal X-ray diffraction analysis.

Keywords: Arsindoline B, bis(indolyl)methanes, indole, streptindole, triethylborane.

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Article Details

VOLUME: 12
ISSUE: 5
Year: 2015
Page: [332 - 336]
Pages: 5
DOI: 10.2174/1570178612666150220225335

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