182. Novel Access to Furan-3-thiols and Derivatives, Impact Meat-Flavor Compounds

Article abstract of DOI:10.1002/hlca.19930760711

A versatile process for the preparation of a number of 3-thio-substituted furans 1-4 is described.These products have very low odor thresholds and are thus potent flavor compounds.Fur-3-yl thiocyanates 10a,b as well as other S-containing analogues (2b, 7a, b, and 8) were prepared by a Michael-type addition of thiocyanic acid, thioacetic acid, alkanethiols, and sodium thiosulfate to alkynones 6 and 15, followed by cyclization (Schemes 3 and 4).The thiocyanates 10a, b were converted to mixed disulfides 3, symmetric disulfides 4, thioethers 2, and thiols 1, using 'hard' or 'soft' nucleophiles or reducing agents, respectively (Scheme 6).