299198-19-9

Upstream product

• 326-91-0 1,1,1-trifluoro-4-(2-thienyl)butane-2,4-dione 
• 104960-50-1 4-(trifluoromethyl)-1,2-dihydro-6-(thiophen-2-yl)-2-thioxopyridine-3-carbonitrile 
• 79-07-2 Chloroacetamide 

Downstream Products

• 331466-74-1 2-phenyl-7-(thiophen-2-yl)-9-(trifluoromethyl)-2,3-dihydropyrido[3',2':4,5]thieno[3,2-d]pyrimidin-4(1H)-one 

Relevant academic research and scientific papers

Fluorine-containing heterocycles: Part I. Synthesis of new 7-(2-thienyl)-9-trifluoromethylpyrido[3′,2′:4,5]thieno[3,2-d] pyrimidines and related fused tetracyclic systems

3-amino-6-(2-thienyl)-4-trifluoromethylthieno[2,3-b]pyridine-2-carboxamide (3) and 2-carbonitrile analogue 5 were prepared by reaction of 3-cyano-6-(2-thienyl)-4-trifluoromethylpyridine-2(1H)-thione (1) with chloroacetamide or chloroacetonitrile respectively. Heating compound 3 with triethyl orthoformate led to the formation of pyridothienopyrimidinone derivative 6. Reaction of 6 with phosphorus oxychloride produced 4-chloropyrimidine derivative 7 which underwent some nucleophilic displacements upon treatment with thiourea, piperidine, morpholine or hydrazine hydrate to give the target 4-substituted pyridothienopyrimidines 8, 10a, 10b and 11 respectively. Reaction of compound 8 with methyl iodide or ethyl chloroacetate gave compounds 9a,b. The condensation of 3-amino-6-(2-thienyl)-4- trifluoromethyl-thieno[2,3-b]pyridine-2-carbonitrile (5) with triethyl orthoformate led to the formation of methanimidate derivative 21 which upon treatment with hydrazine hydrate gave the target 3-amino-3,4-dihydro-4-imino-7- (2-thienyl)-9-trifluoromethylpyrido[3′,2′:4,5] thieno[3,2-d] pyrimidine (22). The reactions of compounds 11 and 22 with some reagents namely; triethyl orthoformate, acetic anhydride, formic acid, acetic acid, acetylacetone benzaldehyde and/or diethyl malonate were carried out and their products were identified, in most cases as [1,2,4] triazolopyridothienopyrimidines via Dimroth rearrangement.

Fluorine-containing heterocycles: Synthesis and some reactions of new 3-amino-2-functionalized-6-(2′-thienyl)-4-trifluoromethylthieno [2,3-b]pyridines

3-Cyano-6-(2′-thienyl)-4-trifluoromethylpyridine-2(1H)-thione (2) was prepared and reacted with chloroacetone or phenacyl bromide to yield the 2-acetyl or benzoyl-3-amino-6-(2′-thienyl)-4-trifluoromethylthieno[2,3-b]pyridines (3a, b). In contrast, the reaction of 2 with chloroacetamide or its N-aryl derivatives gave the corresponding 2-carbamoylmethyl thiopyridines 4a-c. Upon treatment of these educts with K2CO3 or C2H5ONa in ethanol, they underwent intramolecular Thorpe-Ziegler cyclization to afford 3-amino-2-carbamoyl-6-(2′-thienyl)-4-trifluoromethyl-thieno[2,3-b]pyrid ine (5a) and its N-aryl analogs 5b, c. Compounds 5a-c underwent some reactions to yield new pyrido[3',2':4,5]thieno[3,2-d]pyrimidines and pyrido[3′,2′:4,5]thieno[3,2-d][1,2,3] triazines.