Ethyl 5-cyano-1,6-dihydro-2-methyl-4-(2'-thienyl)-6-thioxonicotinate () was synthesized and reacted with ethyl chloroacetate in the presence of sodium acetate or sodium carbonate to give ethyl 5-cyano-6-((2-ethoxy-2-oxoethyl)thio)-2-methyl-4-(2'-thienyl)nicotinate () or its isomeric thieno[2,3-]pyridine . 3-Aminothieno[2,3-]pyridine-2-carboxamide was also synthesized by the reaction of with 2-chloroacetamide. The reaction of with hydrazine hydrate in boiling ethanol gave acethydrazide .
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July 2024
Ethyl-2-((8-cyano-3,5,9a-trimethyl-1-(4-oxo-4,5-dihydrothiazol-2-yl)-4-phenyl-3a,4,9,9a-tetrahydro-1-pyrazolo[3,4-]isoquinolin-7-yl)thio)acetate () was synthesized, and its structure was characterized by IR, MS, and NMR (H and C) and verified by a single-crystal X-ray structure determination. Compound adopts a "pincer" conformation. In the crystal, the hydrogen bonds of -H···O, C-H···O, and O-H···S form thick layers of molecules that are parallel to (101).
View Article and Find Full Text PDFThe synthesis of two new hexahydroisoquinoline-4-carbonitrile derivatives ( and ) is reported along with spectroscopic data and their crystal structures. In compound , the intramolecular O-H···O hydrogen bond constraints the acetyl and hydroxyl groups to be . In the crystal, inversion dimers are generated by C-H···O hydrogen bonds and are connected into layers parallel to (10-1) by additional C-H···O hydrogen bonds.
View Article and Find Full Text PDFThe reaction of ethyl 5-cyano-2-methyl-4-(thiophen-2-yl)-6-thioxo-1,6-dihydropyridine-3-carboxylate () with 2-chloroacetamide or its -aryl derivatives gave ethyl 6-((2-amino-2-oxoethyl)thio)-5-cyano-2-methyl-4-(thiophen-2-yl) nicotinate () or its -aryl derivatives -, respectively. Cyclization of - into their isomers - was carried out by heating in absolute ethanol in the presence of a catalytic amount of sodium ethoxide. The -aminoamide was reacted with some aryl aldehydes in refluxing ethanol containing a few drops of conc.
View Article and Find Full Text PDFThree new series of isoquinolines, that is, 7-acetyl-3-acetonylsulfanyl-8-aryl-1,6-dimethyl-6-hydroxy-5,6,7,8-tetrahydroisoquinoline-4-carbonitriles (-); 3-acetonylsulfanyl-8-aryl-1,6-dimethyl-7,8-dihydroisoquinoline-4-carbonitriles (-); and 7-acetyl-8-aryl-1,6-dimethyl-3-ethylsulfanyl-7,8-dihydroisoquinoline-4-carbo-nitriles (,) were carefully synthesized. Also, pyrazoloisoquinoline was used as a precursor for synthesis of 7-ethylsulfanyl-4-phenyl-1-thiocarbamoyl-3,5,9a-trimethyl-3a,4,9,9a-tetrahydro-1-pyrazolo[3,4-g]isoquinoline-8-carbonitrile (); 7-benzyl-sulfanyl-4-phenyl-1-thiocarbamoyl-3,5,9a-trimethyl-3a,4,9,9a-tetrahydro-1-pyrazolo[3,4-]isoquinoline-8-carbonitrile (); and 7-ethylsulfanyl-1-(4-oxo-4,5-dihydrothiazol-2-yl)-4-phenyl-3,5,9a-trimethyl-3a,4,9,9a-tetrahydro-1-pyrazolo[3,4-]isoquinoline-8-carbonitrile (). Moreover, the crystal structures of two representative compounds were determined.
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