Synthesis of cannabimimetic indoles containing non-carbonyl bioisosters

Abstract

A new one-pot synthetic methodology of cannabimimetic indole is developed. Neither special apparatus nor exotic reagent is required for the reaction. The polymeric by-products from the reaction are suppressed by continuous nitrogen flow. Yield of the reaction are satisfactory up to 86 percent. Several novel cannabimimetic indoles analogs which the carbonyl group is replaced by other bioisosteres are also synthesized. The synthetic methodology of thiocarbonyl, thiol, exo-methylene and carbinol analogs starting from one-pot ketone product is investigated. The synthesis of other analogs including alkyl, sulfenyl and sulfonyl from indole is also investigated.