Issue 96, 2014
From the journal:

RSC Advances

Rhodium(i)-catalysed “ene-type” cycloisomerization of N-[2-(2-alkyn-1-yl)phenyl]carbodiimides leading to 3-(cis-alken-1-yl)-2-aminoquinolines†

Takashi Otani,*ab   Misato Onishi,a   Takafumi Seino,a   Naoki Furukawaa  and  Takao Saito*a  

* Corresponding authors

a Department of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku, Tokyo 162-8601, Japan
E-mail: tsaito@rs.kagu.tus.ac.jp
Fax: +81 (0)3-5261-4631

b Research Center for Chirality, Research Institute for Science & Technology, Tokyo University of Science, Kagurazaka, Shinjuku, Tokyo 162-8601, Japan
E-mail: totani@rs.tus.ac.jp
Fax: +81 (0)3-5261-4631

Abstract

Cycloisomerization of N-[2-(2-alkyn-1-yl)phenyl]carbodiimides 1 catalysed by Rh(dppp)2Cl under heating conditions afforded 3-(cis-alken-1-yl)-2-(substituted amino)quinolines in up to 87% yield with high cis-selectivity. Scope, limitations, a proposed mechanism for these reactions, and a one-pot synthesis of their trans-isomers from 1 with iodine-promoted olefin isomerization are described.

Graphical abstract: Rhodium(i)-catalysed “ene-type” cycloisomerization of N-[2-(2-alkyn-1-yl)phenyl]carbodiimides leading to 3-(cis-alken-1-yl)-2-aminoquinolines

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Article information

DOI
https://doi.org/10.1039/C4RA11846D
Article type
Communication
Submitted
18 Sep 2014
Accepted
13 Oct 2014
First published
14 Oct 2014

RSC Adv., 2014,4, 53669-53673

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Rhodium(I)-catalysed “ene-type” cycloisomerization of N-[2-(2-alkyn-1-yl)phenyl]carbodiimides leading to 3-(cis-alken-1-yl)-2-aminoquinolines

T. Otani, M. Onishi, T. Seino, N. Furukawa and T. Saito, RSC Adv., 2014, 4, 53669 DOI: 10.1039/C4RA11846D

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