Synthesis, Structure and Properties of Some Thiophene‐Containing Sulfamido Acids.

Abstract

Acids. -(TYUNEVA, I. V.; FILIMONOV, S. I.; SOLOV'EV, M. Y.; KRAVCHENKO, D. V.; BALAKIN, K. V.; SKORENKO, A. V.; DOROGOV, M. V.; Izv. Vyssh.

A Convenient Synthesis of Novel 3-(Heterocyclylsulfonyl)propanoic Acids and their Amide Derivatives

“…We used these acids as starting reagents for the preparation of a large library of carboxamides via the corresponding acid chlorides. 5 We found this general scheme suitable for preparation of other 3-(heterocyclylsulfonyl)propanoic acids and their amide derivatives (Scheme 1). At the first step, chlorosulfonates 2a-h were obtained in good yields (39-88%) by reacting the heterocyclic compounds 1a-h with a mixture of chlorosulfonic acid and PCl 5 (Method A) or with chlorosulfonic acid (Method B) at elevated temperature.…”

“…Recently, we reported a convenient synthetic method for preparation 3-(2-thienylsulfonyl)propanoic and 3-(5-bromo-2-thienylsulfonyl)propanoic acids and the corresponding carboxamide derivatives. 5 The synthetic scheme included sulfochlorination of thiophene or 2-bromothiophene, treatment of 2-thienylchlorosulfonates with sodium sulfite and the reaction of the resulting sodium sulfinates with acrylic acid. The desired sulfonylpropionates were obtained in high yields (generally, in the range of 50-70% from the initial heterocycles) and excellent purity using easy purification procedures, such as precipitation from the reaction mixtures and recrystallization.…”

“…The results provide further confirmation of the scope and generality of the applied approach to different 3-sulfonylpropionate derivatives of heterocyclic compounds: >1000 analogues of these molecules have been made in our laboratories in the past two years by parallel synthesis methods. 5 Melting points were measured with a Koeffler melting point apparatus and are uncorrected. 1 H NMR spectra were recorded on a Bruker AMX-400 spectrometer in DMSO-d 6 using TMS as an internal standard (chemical shifts in ppm).…”