A new mode of aromatic metamorphosis has been developed, which allows thiophenes and their benzo-fused derivatives to be converted a variety exotic heteroles. This transformation involves 1) the efficient generation key 1,4-dianions by means desulfurative dilithiation with lithium powder 2) subsequent trapping dianions heteroatom electrophiles in one-pot manner. Via dilithiation, sulfur atoms a...

In this study, an effort has been made to analyze the aromaticity of oligomers phenylenes and thiophenes, with presence absence linkers using Nucleus-Independent Chemical Shift (NICS) as a descriptor. The relation between HOMO–LUMO gaps, reorganization excitation energies respective NICS values employed develop structure-aromaticity-conjugation spectroscopy relationship (SACSR). Results show th...

A Pd(II)-catalyzed Sonogashira type cross-coupling reaction between 2-iodothiophenol and phenylacetylene has been developed. A series of 2-substituted benzo[b]thiophenes were obtained in moderate to good yield (up to 87%). The application of this method was demonstrated by the synthesis of 2-(4-(tert-butyl)phenyl)benzo[b]thiophene 1,1-dioxide and (4-methoxyphenyl)(2-(4-methoxyphenyl) benzo[b]th...

A series of arylidene anabaseines were synthesized to probe the functional impact of hydrogen bonding on human α7 nicotinic acetylcholine receptor (nAChR) activation and desensitization. The aryl groups were either hydrogen bond acceptors (furans), donors (pyrroles), or neither (thiophenes). These compounds were tested against a series of point mutants of the ligand-binding domain residue Gln-5...