Cyclization of Activated Methylene Isocyanides with Methyl N(N),N′-Di(tri)substituted Carbamimidothioate: A Novel Entry for the Synthesis of N,1-Aryl-4-tosyl/ethoxycarbonyl-1H-imidazol-5-amines

Abstract

Base-induced cyclization of active methylene isocyanides with carbamimidothioates for the synthesis of N,1-aryl-4-tosyl/ethylcarboxy-1H-imidazol-5-amines is reported. The diversity of the reactions is exemplified by using various carbamimidothioates obtained from symmetrical N,N-disubstituted, unsymmetrical N,N,N-trisubstituted, and unsymmetrical N,N-disubstituted thioureas. This diversity is further enriched by different isocyanides. A mechanism for the formation of the title compounds is proposed.

Reductive Coupling of Aromatic Aldehydes and Ketones Under Electrochemical Conditions

“…33 To the best of our knowledge, phenyl-carbonyl coupling reactions are not reported under electrochemical conditions. In continuation of our efforts in organic synthesis, [34][35][36][37][38][39][40][41][42][43][44][45][46][47] we report here-in phenyl-carbonyl reductive coupling of o-substituted aromatic carbonyl compounds (Scheme 1c) and carbonyl-carbonyl reductive coupling of m-substituted carbonyl compounds (Scheme 1d).…”

Condensation of Amines with S-Methyl Thiouronium Salts: Another Entry for the Synthesis of Amidines

“…We have recently developed -oxodithio esters, 30,31 2oxoethanimidothioates, 32 2-oxo-2-(amino)ethanedithioates, 33 carbimidothioates, 34 xanthate esters, 35 and carbamimidothioates 36,37 as potential key intermediates in organic synthesis. In this direction, we report a potential application of S-methyl thiouronium salts in the synthesis of N,N,N′-trisubstituted amidines.…”

An Efficient Copper-Mediated Route for the Synthesis of 2-Substituted Benzothiazoles from Dithioesters and Investigation of Their Antibacterial Activities

“…The required organosulfur intermediates were prepared following our previously reported protocol. 18j b c e g h j The progress of the reactions was continuously monitored using TLC on pre-coated sheets of silica gel (Merck 60F254, 0.25 mm thickness). Visualization of the TLC plates was achieved using UV light.…”