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Issue 42, 2014
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Triflic acid-promoted cycloisomerization of 2-alkynylphenyl isothiocyanates and isocyanates: a novel synthetic method for a variety of indole derivatives†

Takao Saito,*a   Yoshihiko Sonoki,a   Takashi Otani*a  and  Noriki Kutsumuraab  
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* Corresponding authors

a Department of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan
E-mail: tsaito@rs.kagu.tus.ac.jp, totani@rs.tus.ac.jp

b International Institute for Integrative Sleep Medicine (WPI-IIIS), University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8577, Japan

Abstract

A new approach towards the synthesis of indole derivatives via triflic acid-promoted cycloisomerization with rearrangement of 2-(alkyn-1-yl)phenyl isothiocyanates and 2-(alkyn-1-yl)phenyl isocyanates has been achieved. By this methodology, structurally diverse types of indole derivatives such as thieno- and furo-indoles, spiro-indolethiones, spiro-oxindoles, and 3-alkylidene-oxindoles were synthesized.

Graphical abstract: Triflic acid-promoted cycloisomerization of 2-alkynylphenyl isothiocyanates and isocyanates: a novel synthetic method for a variety of indole derivatives

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Article information

https://doi.org/10.1039/C4OB00825A
Submitted
22 Apr 2014
Accepted
19 Jun 2014
First published
20 Jun 2014
Org. Biomol. Chem., 2014,12, 8398-8407
Article type
Paper
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Triflic acid-promoted cycloisomerization of 2-alkynylphenyl isothiocyanates and isocyanates: a novel synthetic method for a variety of indole derivatives

T. Saito, Y. Sonoki, T. Otani and N. Kutsumura, Org. Biomol. Chem., 2014, 12, 8398
DOI: 10.1039/C4OB00825A

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