Issue 19, 2008
From the journal:

Organic & Biomolecular Chemistry

One-pot synthesis of 6-(thien-2-yl)- and 6-(fur-2-yl)salicylates based on regioselective [3 + 3] cyclocondensations of 1,3-bis(trimethylsilyloxy)-1,3-butadienes†

Ibrar Hussain,a   Abdolmajid Riahi,a   Mirza Arfan Yawer,a   Alexander Villinger,a   Christine Fischer,ab   Helmar Görlsc  and  Peter Langer*ab  

* Corresponding authors

a Institut für Chemie, Universität Rostock, Albert-Einstein-Str. 3a, Germany
E-mail: peter.langer@uni-rostock.de
Fax: 00 49 381 49864112
Tel: 0049 381 4986410

b Leibniz-Institut für Katalyse e. V. an der Universität Rostock, Albert-Einstein-Str. 29a, Germany

c Institut für Anorganische und Analytische Chemie, Universität Jena, August-Bebel-Str. 2, Germany

Abstract

6-(Thien-2-yl) and 6-(fur-2-yl)salicylates are prepared by TiCl4-mediated [3 + 3] cyclocondensations of 1,3-bis(trimethylsilyloxy)-1,3-butadienes with 3-(thien-2-yl)- and 3-(fur-2-yl)-3-silyloxy-2-en-1-ones, respectively. The regioselectivity of the cyclization depends on the substitution pattern of the 3-silyloxy-2-en-1-one.

Graphical abstract: One-pot synthesis of 6-(thien-2-yl)- and 6-(fur-2-yl)salicylates based on regioselective [3 + 3] cyclocondensations of 1,3-bis(trimethylsilyloxy)-1,3-butadienes

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Article information

DOI
https://doi.org/10.1039/B803472A
Article type
Paper
Submitted
28 Feb 2008
Accepted
28 May 2008
First published
16 Jul 2008

Org. Biomol. Chem., 2008,6, 3542-3551

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One-pot synthesis of 6-(thien-2-yl)- and 6-(fur-2-yl)salicylates based on regioselective [3 + 3] cyclocondensations of 1,3-bis(trimethylsilyloxy)-1,3-butadienes

I. Hussain, A. Riahi, M. A. Yawer, A. Villinger, C. Fischer, H. Görls and P. Langer, Org. Biomol. Chem., 2008, 6, 3542 DOI: 10.1039/B803472A

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