title: Application of Ynamides in the Synthesis of 2-(Tosylamido)- and 2,5-Bis(tosylamido)thiophenes.
abstract: A step-economic and metal-catalyst-free synthesis of 2-(tosylamido)- and 2,5-bis(tosylamido)-thiophenes from nonsymmetrical 1,3-butadiynamides and symmetrical 1,3-butadiyne-1,4-diamides is reported. The reaction proceeds in the presence of Na2S·9H2O (2-3 equiv) under mild reaction conditions (50 °C) and is facilitated by polarized carbon-carbon triple bonds in ynamides. This new approach to thiophenes based on the chemistry of ynamides was applied to the synthesis of a bis(tosylamido)-capped terthiophene having a string of N,S-heteroatoms embedded in a highly π-conjugated molecular frame.
authors.affiliation: Laboratoire de Chimie Moléculaire et Thioorganique, CNRS UMR 6507, Normandie Univ, ENSICAEN & UNICAEN , 6 bvd Maréchal Juin, 14050 Caen, France.|Laboratory of Heteroatom Organic Chemistry, University of Carthage, Faculty of Sciences of Bizerte , 7021 Jarzouna, Tunisia.
authors.forename: Imen
authors.initials: I
authors.lastname: Talbi
authors.affiliation: Laboratoire de Chimie Moléculaire et Thioorganique, CNRS UMR 6507, Normandie Univ, ENSICAEN & UNICAEN , 6 bvd Maréchal Juin, 14050 Caen, France.
authors.forename: Carole
authors.initials: C
authors.lastname: Alayrac
authors.affiliation: Laboratoire de Chimie Moléculaire et Thioorganique, CNRS UMR 6507, Normandie Univ, ENSICAEN & UNICAEN , 6 bvd Maréchal Juin, 14050 Caen, France.
authors.forename: Jean-François
authors.initials: JF
authors.lastname: Lohier
authors.affiliation: Laboratory of Heteroatom Organic Chemistry, University of Carthage, Faculty of Sciences of Bizerte , 7021 Jarzouna, Tunisia.
authors.forename: Soufiane
authors.initials: S
authors.lastname: Touil
authors.affiliation: Laboratoire de Chimie Moléculaire et Thioorganique, CNRS UMR 6507, Normandie Univ, ENSICAEN & UNICAEN , 6 bvd Maréchal Juin, 14050 Caen, France.
authors.forename: Bernhard
authors.initials: B
authors.lastname: Witulski