A number of 3,4-dialkoxythiophene compounds have been synthesised and their reactivities assessed via the Mannich reaction with secondary amines. These reactions surprisingly gave the bis-Mannich bases substituted at the 2- and 5-positions as well as the expected mono-Mannich bases substituted at the 2-position. Conditions were optimised to give symmetrical bis-2,5-Mannich bases in one step and asymmetrical bis-2,5-Mannich bases in two steps. Several bis(thien-2-ylmethyl)amines derived from 3,4-dialkoxythiophenes are reported, their synthesis being performed under both normal and high dilution conditions. Some syntheses also afforded the (thien-2-ylmethyl)amine oligomers. Further substitution of the bis(thien-2-ylmethyl)amines at the 5-position via the Mannich reaction also proved successful. The factors affecting the yields and substitution patterns are discussed, together with molecular modelling of the spatial requirements.
You have access to this article
Please wait while we load your content...
Something went wrong. Try again?