Synthesis of 3-amino-4-methyl-6-trifluoromethylthieno[2,3-b]pyridine-2-carboxanilide and its crystal and molecular structure

Nikishin, K. G.; Нестеров, В. Н.; Кислый, В. П.; Шестопалов, А. М.; Семенов, В. В.

doi:10.1007/bf02495978

Cited by 7 publications

(12 citation statements)

References 4 publications

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“…The results of X-ray diffraction analysis of 3d and 4j are in agreement with the proposed regioselectivity of alkylation of 1 and 2 . , The structural parameters of 3d and 4j are typical of these types of compounds. , X-ray studies of 3d also showed substantial divergence of the ethyl group out of the plane of the heterocyclic ring. This conformation is probably affected by intramolecular nonvalence contacts between the nitrogen atom in the pyridine ring and an α-hydrogen or carbon atoms of the CH 3 CH 2 S− group.…”

Section: Resultssupporting

confidence: 82%

“…Full details of the X-ray analysis of 3d and 4j were presented elsewhere. 23,24 Our experiments demonstrated that both S-alkyl derivatives 3a-s and 3-aminothieno[2,3-b]pyridines 4h-u can be produced in satisfactory yields using uniform conditions (see Experimental Section and Table 1). However, the best results can be achieved at optimal reaction times.…”

Section: Resultsmentioning

confidence: 79%

“…The results of X-ray diffraction analysis of 3d and 4j are in agreement with the proposed regioselectivity of alkylation of 1 and 2. 23,24 The structural parameters of 3d and 4j are typical of these types of compounds. 25,26 X-ray studies of 3d also showed substantial divergence of the ethyl group out of the plane of the heterocyclic ring.…”

Section: Resultsmentioning

confidence: 99%

“…Such flattening of the molecule is favored by the intramolecular hydrogen bonding. Full details of the X-ray analysis of 3d and 4j were presented elsewhere. , …”

Section: Resultsmentioning

confidence: 99%

“…Synthesis of 3d and 4j was reported previously. 23,24 3-Cyano-2-alkylthiopyridines (3a-s). General Procedure.…”

Section: Methodsmentioning

confidence: 99%

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Preparation of Trifluoromethylpyridine Libraries

Шестопалов

Кислый²,

Kruglova³

et al. 1999

J. Comb. Chem.

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S-Alkylation followed by heterocyclization of trifluoromethyl-3-cyano-2(1H)-pyridinethiones was used for preparation of libraries of S-alkyl trifluoromethylpyridines and thieno[2,3-b]pyridines. The S-alkylation (in water--DMF mixtures) was successful for all 18 alkylating agents employed (yields typically > 50%). S-Alkyl derivatives were further converted to corresponding thieno[2,3-b]pyridines via heterocyclization in base conditions (yields > 65%). Structures of new compounds were elucidated by a combination of IR and 1H NMR spectroscopy and elemental analysis and were confirmed by means of single-crystal X-ray diffraction analysis.

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Section: Resultssupporting

confidence: 82%

Section: Resultsmentioning

confidence: 79%

Section: Resultsmentioning

confidence: 99%

“…Such flattening of the molecule is favored by the intramolecular hydrogen bonding. Full details of the X-ray analysis of 3d and 4j were presented elsewhere. , …”

Section: Resultsmentioning

confidence: 99%

“…Synthesis of 3d and 4j was reported previously. 23,24 3-Cyano-2-alkylthiopyridines (3a-s). General Procedure.…”

Section: Methodsmentioning

confidence: 99%

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