Regioselective synthesis of 5-ethoxycarbonyl-, 5-acetyl-and 5-trifluoroacetyl-6-trifluoromethylsalicylates by one-pot cyclizations of 1, 3-bis (trimethylsilyloxy)-1, 3- …

…, NK Kelzhanova, ZA Abilov, H Feist, P Langer

Index: Ladzik, Simone; Lubbe, Mathias; Kelzhanova, Nazken K.; Abilov, Zharylkasyn A.; Feist, Holger; Langer, Peter Journal of Fluorine Chemistry, 2012 , vol. 136, p. 38 - 42

Full Text: HTML

Citation Number: 1

Abstract

5-Ethoxycarbonyl-, 5-trifluoroacetyl-, and 5-acetyl-6-trifluoromethylsalicylates were prepared by one-pot cyclizations of 1, 3-bis (trimethylsilyloxy)-1, 3-butadienes with 3-alkoxy-2-alken-1- ones. The reactions proceeded with very good regioselectivity by conjugate addition of the terminal carbon atom of the diene to the enone and subsequent cyclization. The cyclization proceeded in most cases via the trifluoroacetyl group.