ALLYLDIPHENYLGUANIDINE COMPLEX WITH ARYLTELLURIUM THRICHLORIDE

Abstract

Functionalized acyclic and cyclic guanidines have a wide range of biological activity. In particular, they possess antitumor, antibacterial activities, are immunosuppressants, anesthetics, analgesics and analogues of natural alkaloids. The search of methods for the synthesis of new guanidine derivatives is an urgent problem.
 The introduction of an unsaturated alkyl substituent to the guanidine backbone opens the way to the synthesis of heterocyclic compounds of the azole or azine series using the method of electrophilic heterocyclization under the action of halogen-containing electrophilic agents. For this purpose, N-allyl-N ',N' '- diphenylguanidine was synthesized according to the described procedure. Allyl substituted guanidines are able to cyclize under the action of iodine. The use of a chalcogen halogen-containing electrophile may lead to the formation of a potentially biologically active acyclic or heterocyclic guanidine derivative. For this purpose, p-methoxyphenyltellurium trichloride was used as an electrophilic agent.
 Reaction of equimolar amounts of N-allyl-N',N''-diphenylguanidine and p-methoxy-phenyltellurium trichloride was performed in chloroform with a minor amount of THF. It was found that with 12 hours of reagents stirring, adducts of the substrate-electrophile composition 1: 1 are formed. The structure of the complex is proposed on a basis of spectral data and elemental analysis data. The increasing of the reaction time and temperature does not lead to the formation of addition or cyclization products.