367280-29-3Relevant academic research and scientific papers
The preparation of novel thiophene-based macrocyclic Mannich bases
Chaffin,Barker,Huddleston
, p. 1398 - 1405 (2007/10/03)
A range of macrocyclic thiophene-based Mannich bases containing 10-22-membered rings has been prepared. The starting materials for the synthesis were substances of the type ArO-Z-OAr (where Ar = 2-methoxycarbonyl-3-thienyl and Z = alkyl or heteroalkyl), which were made by the reaction of α,ω -dihalides or -bis(toluene-p-sulfonate)s with two moles of methyl 3-hydroxythiophene-2-carboxylate. Saponification and subsequent decarboxylation of these compounds afforded the corresponding α,ω-bis(3-thienyloxy)alkanes. Macrocyclic Mannich bases were prepared from these ethers by aminomethylation. High dilution conditions were not required in many cases and, in the case of the heteroalkyl-bridged ethers, this is believed to be due to an internal template effect enhancing the yield.
Novel Thiophene-based Macrocycles related to Azacrown Ethers
Barker, John M.,Chaffin, Julie D. E.,Halfpenny, Joan,Huddleston, Patrick R.,Tseki, Potlaki F.
, p. 1733 - 1734 (2007/10/02)
A range of compounds containing two 3-oxygenated thiophene rings linked through the oxygen atoms by a variety of alkyl and heteroalkyl chains has been prepared and subjected to electrophilic substitution, at C(2) and C(2'), giving, inter alia, bis-Mannich
