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Issue 19, 2008
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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

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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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Publication details

The article was received on 28 Feb 2008, accepted on 28 May 2008 and first published on 16 Jul 2008


Article type: Paper
DOI: 10.1039/B803472A
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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