Production of alkane and cyclohexane derivatives with two heterocyclic substituents of the furan, pyrrole, and thiophene series

Heating 1,2,11,12-tetrachloro-2,11-bis(R-4,9-dodecanediones) and 1,4-bis(3-R-3,4-dichlorobutanoyl)cyclohexanes gave, respectively, 1,4-difuryl derivatives of butane and cyclohexane, while treatment of them with primary amines or phosphorus pentasulfide in DMF was used to synthesize dipyrryl and dithienyl compounds. 1-R-3-R1-3,4-Dichlorobutanones react with ethylenediamine in aqueous alkali solutions to give 1,2-dipyrryl or monopyrryl derivatives of ethane.