A B C
Z. Naturforsch. 2013, 68b, 1021 – 1030
doi:10.5560/ZNB.2013-3123
Synthesis of Functionalized Acetophenones by Formal [3 + 3] Cyclocondensations of 1,3-Bis(silyloxy)-1,3-butadienes with 3-Alkoxy- and 3-Silyloxy-2-acetyl-2-en-1-ones
Rüdiger Dede1, Abdolmajid Riahi1,2, Mohanad Shkoor1, Mirza A. Yawer1, Ibrar Hussain1, Nazken Kelzhanova1,3, Zharylkasyn A. Abilov3, Abiodun Falodun1,4, Helmar Görls5, and Peter Langer1,2
1 Institut für Chemie, Universität Rostock, Albert Einstein Str. 3a, 18059 Rostock, Germany
2 Leibniz-Institut für Katalyse an der Universität Rostock e.V., Albert Einstein Str. 29a, 18059 Rostock, Germany
3 Al-Farabi Kazakh National University, Al-Farabi ave. 71, 050040 Almaty, Kazakhstan
4 Department of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Benin, Benin City, Nigeria
5 Universität Jena, Institut für Anorganische und Analytische Chemie, Humboldtstr. 8, 07743 Jena
Reprint requests to Prof. Peter Langer. E-mail: peter.langer@uni-rostock.de
Received April 29, 2013 / published online September 4, 2013
The TiCl4-mediated cyclization of 1,3-bis(silyloxy)-1,3-butadienes with 2-acetyl-1-silyloxybut-1-en-3-one and 3-acetyl-4-silyloxypent-3-en-2-one, readily available from 3-(formyl)acetylacetone and 3-(acetyl)acetylacetone (triacetylmethane), afforded a variety of functionalized acetophenones.
Key words: Cyclizations, Arenes, Regioselectivity, Acetophenones, Silyl Enol Ethers
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