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Synthesis of bis(indolyl)methanes Catalyzed by Triethylborane

[ Vol. 12 , Issue. 5 ]

Author(s):

J. Pablo Garcia Merinos, Heraclio Lopez Ruiz, Yliana Lopez and Susana Rojas   Pages 332 - 336 ( 5 )

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.

Affiliation:

Lima Area Academica de Quimica, Universidad Autonoma del Estado de Hidalgo, Carretera Pachuca-Tulancingo Km. 4.5, Mineral de La Reforma, Hidalgo, CP 42076, Mexico and Instituto de Investigaciones Quimico-Biologicas, Universidad Michoacana de San Nicolas de Hidalgo, Ed.B-1, C.U., Morelia, Michoacan, 58030, Mexico.



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