First Synthesis of 3-Acetyl-2-aminothiophenes Using the Gewald Reaction

Abstract

Novel 3-acetyl-2-aminothiophenes were prepared from cyanoacetone and 1,4-dithianyl-2,5-diols using a modified Gewald reaction. The syntheses of the corresponding acetamides, as well as that of 3-acetyl-2-amino-5-nitrothiophene -an interesting building-block for thiophene azo dyes -are reported. Detailed spectroscopic investigations ( 1 H-NMR, 13 C-NMR, MS, IR) of the obtained compounds are presented.

Electrochemical oxidation of catechols in the presence of cyanoacetone and methyl cyanoacetate

“…Among the carbon centered nucleophiles, methyl cyanoacetates and cyanoacetone, have received considerable attention [9][10][11][12][13]. The reaction adducts often undergo further reactions such as Knovenagel reaction or electrophilic reaction of nitrile group [2,[14][15][16]. To the best of our knowledge there are few reports about nucleophilic reaction of their enolic hydroxy group [13].…”

Activated bentonite promoted Friedländer condensation reactions: Synthesis of thieno[2,3-b]quinolinones and tacrines analogues derivatives

“…The starting material 2-aminothiophene-3-carbonitrile 1 was prepared in one step from corresponding ketones by using versatile Gewald reaction [16,17] (Scheme 1).…”

Basic Ionic Liquid [bmIm]OH–Mediated Gewald Reaction as Green Protocol for the Synthesis of 2-Aminothiophenes

“…Majority of GR applications include use of organic bases such as morpholine [11,12] , triethylamine [13,14] , A c c e p t e d M a n u s c r i p t 3 piperidine [15] , pyridine and diethylamine [16] etc. making it environmental unfriendly which necessitated us to investigate GR using TSILs.…”