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Molecules 2019, 24(5), 960; https://doi.org/10.3390/molecules24050960

Convenient Synthesis of 6,7,12,13-Tetrahydro-5H-Cyclohepta[2,1-b:3,4-b’]diindole Derivatives Mediated by Hypervalent Iodine (III) Reagent

1,2
,
1,*
and
1,2,*
1
State Key Laboratory of Drug Research, Department of Medicinal Chemistry, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zu Chong Zhi Road, Shanghai 201203, China
2
School of Pharmacy, University of Chinese Academy of Sciences, No.19A Yuquan Road, Beijing 100049, China
*
Authors to whom correspondence should be addressed.
Academic Editors: Richard A. Bunce, Philippe Belmont, Wim Dehaen and Eugene Babaev
Received: 16 February 2019 / Revised: 4 March 2019 / Accepted: 6 March 2019 / Published: 8 March 2019
(This article belongs to the Collection Heterocyclic Compounds)
Full-Text   |   PDF [3049 KB, uploaded 8 March 2019]   |  

Abstract

Bisindolyl alkaloids represent a large family of natural and synthetic products that display various biological activities. Among the bisindole compounds, 6,7,12,13-tetrahydro-5H-cyclohepta[2,1-b:3,4-b’]diindoles have received little attention. Only two methods have been developed for the construction of the 6,7,12,13-tetrahydro-5H-cyclohepta[2,1-b:3,4-b’]diindole scaffold thus far, including the classical Fischer indole synthesis conducted by reacting indole-fused cycloheptanone and hydrazines, and the condensation reaction to build the seven-membered ring. Here, we report for the first time a new route to synthesize 6,7,12,13-tetrahydro-5H-cyclohepta[2,1-b:3,4-b’]diindoles through intramolecular oxidative coupling of 1,3-di(1H-indol-3-yl)propanes in the presence of PIFA, DDQ and TMSCl with moderate to excellent yields. View Full-Text
Keywords: phenyliodine(III)bis(trifluoroacetate); cyclohepta[2,1-b:3,4-b’]diindole; intramolecular oxidative coupling phenyliodine(III)bis(trifluoroacetate); cyclohepta[2,1-b:3,4-b’]diindole; intramolecular oxidative coupling
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Peng, L.; Zhang, X.; Yang, C. Convenient Synthesis of 6,7,12,13-Tetrahydro-5H-Cyclohepta[2,1-b:3,4-b’]diindole Derivatives Mediated by Hypervalent Iodine (III) Reagent. Molecules 2019, 24, 960.

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