3‐Cyano‐5‐ethoxycarbonyl‐6‐methyl‐4‐styrylpyridine‐2(1H)‐thione (3) was prepared by reaction of 2‐cyano‐5‐phenylpenta‐2,4‐dienethioamide (2) with ethyl acetoacetate or by multicomponent reaction of cinnamaldehyde (1), cyanothioacetamide and ethyl acetoacetate in a moderate yield. Reaction of compound 3 with some N‐aryl‐2‐chloroacetamides, in the presence of sodium acetate, gave the corresponding 2‐(N‐arylcarbamoylmethylsulfanyl)‐3‐cyano‐5‐ethoxycarbonyl‐6‐methyl‐4‐styrylpyridines 4a‐f. When compounds 4a‐f were subjected to Thorpe‐Ziegler reaction conditions, they converted into the corresponding 3‐amino‐5‐ethoxycarbonyl‐2‐(N‐arylcarbamoyl)‐6‐methyl‐4‐styrylthieno[2,3‐b]pyridines 5a‐f. Compounds 5a,e,f were reacted, in turn, with 2,5‐dimethoxytetrahydrofuran to furnish the corresponding 3‐(pyrrol‐1‐yl)thieno‐pyridines 6a,e,f. Reactions of 5a‐f with triethyl orthoformate or nitrous acid were also carried out and their products were identified. Structural formulas of all synthesized compounds was characterized and confirmed on the basis of their elemental and spectral analyses.
Ethyl (3-cyano-5-ethoxycarbonyl-6-methyl-4-styryl-2-pyridylsulfanyl)acetate was prepared and reacted with hydrazine hydrate in ethanol to give a mixture of (3-cyano-5-ethoxycarbonyl-6-methyl-4-styryl-2pyridylsulfanyl)acetohydrazide and diethyl 3-amino-6-methyl-4-styrylthieno[2,3-b]pyridine-2,5-dicarboxylate. The latter compound was reacted with 2,5-dimethoxytetrahydrofuran to give 3-(1H-pyrrol-1-yl)thieno [2,3b]pyridine analogue which on treatment with hydrazine hydrate in ethanol furnished 5-ethoxycarbonyl-6methyl-3-(1H-pyrrol-1-yl)-4-styrylthieno[2,3-b]pyridine-2-carbohydrazide. Both acetohydrazide and carbohydrazide were used as precursors for the title compounds.
In the title molecule, C28H25Cl2N3O3S, the heterocyclic portion of the tetrahydroisoquinoline unit is planar while the cyclohexene ring adopts a twist-boat conformation. The two 4-chlorophenyl groups extend away from one side of this unit while the hydroxyl and acetyl groups extend away from the opposite side and form an intramolecular O—H...O hydrogen bond. The crystal packing consists of layers parallel to the bc plane. A Hirshfeld surface analysis of the crystal structure indicates that the most important contributions to the crystal packing are from H...H (37.3%), Cl...H/H...Cl (17.6%), O...H/H...O (11.1%), C...H/H...C (10.9%) and N...H/H...N (9.7%) interactions.
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