Thioamides as Useful Synthons in the Synthesis of Heterocycles

Abstract

in 1972 with a M.S. in chemical technology. In 1977 he received his Ph.D. degree in organic chemistry from Lomonosov State University in Moscow, Russia; his doctoral thesis, "Synthesis of condensed heterocycles from indolylurethanes", was completed under the supervision of Prof. A. N. Kost. From 1977 to 1991, he conducted research on thioamide chemistry and taught organic chemistry at Technical University of Szczecin. He received his habilitation degree in 1991 from Warsaw University of Technology for research on synthesis, reactions, and properties of the thioamide derivatives of benzene and some fivemembered heterocycles.

Gewald reaction: synthesis, properties and applications of substituted 2-aminothiophenes

“…NaHCO 3 , K 2 CO 3 , NaOH). Polar solvents, like DMF, alcohols (methanol, ethanol), 1,4-dioxane enhance the condensation of intermediates -α,β-unsaturated nitriles with sulfur, which are either prepared in situ or externally.…”

“…Page 231 © ARKAT USA, Inc. [1,3]oxazin-4-ones 65 using alkyl 2-aminothiophene carboxylates 62 as a substrates exhibits a facile three step synthesis, as is presented on Scheme 22. Aminothiophenes 62 were converted to isothiocyanato-thiophenes 63 by the thiophosgene method.…”

“…[1][2][3][4][5] The interest in this kind of heterocycles has spread from dye chemistry 6 to modern drug design 7 , biodiagnostics 8 , electronic and optoelectronic devices 9 , conductivity-based sensors 10 and self-assembled superstructures. 11 2-Amino-3-aroylthiophenes are agonist allosteric enhancers at the A 1 adenosine receptor.…”

Development of Atom-Economical Catalytic Asymmetric Reactions under Proton Transfer Conditions: Construction of Tetrasubstituted Stereogenic Centers and Their Application to Therapeutics

“…Thioamides are widely utilized as useful precursors for the synthesis of a broad range of heterocyclic compounds by exploiting their ambident nucleophilic character at both the sulfur and nitrogen atoms. 164) However, they are rarely recognized as carbon pronucleophiles in enantioselective carbon-carbon bondforming reactions. Although there have been sporadic studies using thioamide as nucleophiles with the aid of stoichiometric amounts of reagents, there have been no reports on the catalytic generation of active carbon nucleophiles from thioamides and their integration into enantioselective carbon-carbon bond-forming processes.…”

Facile and efficient synthesis of 4'-thioxo-1',3,3',4,4',6' -hexahydro-1H,2'H-spiro[naphthalene-2,5'-pyrimidin]-1-ones in a three-component Mannich-type reaction

“…High reactivity of the thioamide group towards both electro-and nucleophilic agents, often in conjunction with that of other reactive centers in the molecule, made thioamides handy building blocks of particular importance in the synthesis of heterocyclic systems by inter-and intramolecular cyclization. [1][2][3][4][5] Saturated or partially saturated heterocyclic compounds with a thioamide group were found to be of interest as potential ionic liquid media. 6 Bogdanowicz-Szwed and co-workers reported the base-catalyzed reaction of β-ketothioamides with (E)-β-nitrostyrenes which yielded spiro(indane-1,3′-thiophenes).…”