Synthesis and certain properties of acetylenylindoles

A group of new acetylenic derivatives of indole was synthesized by condensation of 2- and 3-iodoindoles with terminal acetylenes. 3-Iodoindole unsubstituted at the heteroatom is distinguished by an increased tendency to undergo deiodination under the reaction conditions. Chemical transformations of the synthesized acetylenic derivatives were carried out, proceeding with both the retention of and with the participation of the triple bond. In the intramolecular cyclization of vicinal, functionally substituted indolylacetylenes, a tendency is manifested to form six-membered heterocycles. A primary pharmacological investigation of the compounds obtained was carried out. Most of them are slightly toxic, several of the compounds display in high doses indications of neurotropic activity.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 1, pp. 134–141, January, 1990.