4506-71-2Relevant articles and documents
Synthesis of 2-aminothiophenes on ionic liquid phase support using the Gewald reaction
Hu, Yi,Wei, Ping,Huang, He,Han, Shi-Qing,Ouyang, Ping-Kai
, p. 1543 - 1548 (2006)
The first report of the use of task-specific ionic liquid as soluble support for the Gewald synthesis of 2-aminothiophenes is reported in this article. This synthetic method is simple and efficient, and the products are obtained in good to excellent yields with high purities, without the need for chromatographic purification. Copyright Taylor & Francis Group, LLC.
Synthesis, Characterization, and Antibacterial and Anti-Inflammatory Activities of New Pyrimidine and Thiophene Derivatives
Lahsasni, Siham,Al-Hemyari, Dunya A. M.,Ghabbour, Hazem A.,Mabkhoot, Yahia Nasser,Aleanizy, Fadilah S.,Alothman, Asma A.,Almarhoon, Zainab M.
, (2018/08/22)
Substituted[4,5]thieno[2,3-d]thiazolo[3,2-a]pyrimidin-5-one (3a-b) and pyrimidin-5(6H)-imine (3c-e) were synthesized via reaction of the starting compounds, ethyl 2-amino-substituted[b]thiophene-3-carboxylate (2a-c) and 2-amino-substituted [b]thiophene-3-carbonitrile (2d-f), respectively, with 2-bromothiazole. Synthesis of (bromo-substituted[b]thiophen-2-yl)alkanamide derivatives (4a-e) and thieno[2,3-d][1,3]oxazin-4-imine derivative (5) was accomplished via reaction of the starting compounds with bromoalkyl chloride through nucleophilic substitution; however, for the synthesis of compound 5, nucleophilic substitution was followed by nucleophilic addition to a nitrile group to form the oxazinimine ring. 1-(3-cyano-substituted[b]thiophen-2-yl)-3-(4-(trifluoromethyl)phenyl)thiourea derivatives (6a-c) were obtained via reaction of the starting compounds (2d-f) and 4-(trifluoromethyl phenyl)isothiocyanate. The lead compounds (2d-f) rapidly reacted with 4-(trifluoromethyl)benzaldehyde or 4-(2-pyridyl)benzaldehyde in acidic medium to yield compounds (7a-f) in large quantities. X-ray crystallography of compounds 4c and 7e confirmed their structures. Antimicrobial studies revealed that compound 6a was equally potent to ampicillin against Bacillus strains. Moreover, compounds 3e, 4d, and 6a possessed greater anti-inflammatory potency than that of the standard drug.
A simple synthesis of alkyl 2-aminobenzo[ b ]thiophene-3-carboxylates via an unexpected dehydrogenation of alkyl 2-amino-4,5,6,7-tetrahydrobenzo[ b ]thiophene-3-carboxylates
Adib, Mehdi,Bayanati, Maryam,Soheilizad, Mehdi,Ghazvini, Helia Janatian,Tajbakhsh, Mahmood,Amanlou, Massoud
, p. 2918 - 2922 (2015/01/09)
A simple method for the preparation of alkyl 2-aminobenzo[b]thiophene-3-carboxylates is described. Alkyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylates, generated from the Gewald three-component reaction between cyclohexanones, alkyl cyanoacetates and sulfur, undergo dehydrogenation in benzonitrile under an air atmosphere to afford alkyl 2-aminobenzo[b]thiophene-3-carboxylates in good to excellent yields.