Preparation and characterization of cyclic-ketone derivatives of methyl undec-10-enoate and their cyclocondensation with mercaptoacetic acid

Abstract

Reaction of methyl undec-10-enoate <b>2</b> with cyclopentanone <b>1a</b> affords two products, methyl 2-(2'-cyclo­pentano­nyl)undec-10-enoate <b>3a</b> and methyl 11-(2'-cyclopentanonyl)undecanoate <b>4a</b>. Similarly, the reaction of cyclohexanone <b>1b</b> gives two products <b>3b</b> and <b>4b</b>. Compounds <b>4a</b> and <b>4b</b> on further reaction with mercaptoacetic acid and ammonium carbonate yield the products <b>5a</b> and <b>5b</b>, respectively. Products have been characterized by elemental analysis and spectral data. Compounds <b>3a, b, 4a, b </b>and <b>5a,b </b>have been tested for antimicrobial activity. The compounds <b>3a,b</b> and <b>4a,b</b> show negative results at 100 <img src='/image/spc_char/micro.gif' border=0>g/mL whereas the compounds <b>5a,b</b> show positive results at 100 <img src='/image/spc_char/micro.gif' border=0>g/mL.