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Ibrar Hussain

Synthesis of Homophthalates, 2-(Arylsulfonyl)pyridines, 6-(Thien-2-yl)salicylates, Dibenzo[b,d]pyran-6-ones, Trifluoromethyl- and Fluoro-Substituted Biaryls by [4+2] and [3+3] Cyclizations of 1,3-Bis(silyloxy)-1,3-butadienes

Universität Rostock, 2008

Abstract: One-pot cyclization reactions of 1,3-bis(silyl enol ethers) with the different electrophiles provide a convenient approach for the synthesis of various complex carbacycles and heterocycles from simple starting materials. 6-Hetaryl-salicylates and 4-Aryl and 4-Hetaryl-salicylates were prepared based on [3+3] cyclizations of 1,3-bis(sily enol ethers) in an efficient way. Dibenzo[b,d]pyran-6-ones were synthesized by formal [3+3] cyclization of 1,3-bis(silyl enol ethers) with 1-(2-methoxyphenyl)-1-(trimethylsilyloxy)alk-1-en-3-ones and subsequent BBr3-mediated lactonization. Aryl fluorides were synthesized by [3+3] cyclization of 1,3-bis(silyl enol ethers) with 2-fluoro-3-silyloxy-2-en-1-ones. 1,3-Bis(silyl enol ethers) were used efficiently for the synthesis of highly functionalized homomphthalates and 4-hydoxypyridines based on [4+2] cyclization reactions.

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