The multi-component condensation in the synthesis of the substituted 2-alkylsulphanil-4,6-diarilpyridine-3-carbonitriles and their derivatives

Authors

  • I. V. Dyachenko Luhansk Taras Shevchenko National University, Ukraine

DOI:

https://doi.org/10.24959/ophcj.14.809

Keywords:

multi-component condensation, chalcones, alkylhalides, hydrogen sulphide, N-methylmorpholine, cyanothioacetamide, Michael reaction, 2-alkylsulphanilpyridines, thieno[2, 3-b]pyridines, pyrido[3’, 2’, 4, 5]thieno[3, 2-d]pyrimidine

Abstract

The multi-component condensation of chalcones, malononitrile, alkylhalides, hydrogen sulphide and N-methyl-morpholine completes with forming 2-alkylsulphanil-4,6-diarylpyridine-3-carbonitriles, which are used in the synthesis of the substituted 1,4-bis(3-cyano-6’-methoxyphenyl-4’-phenylpyridin-2-ylthio)butane, 3-amino-4,6-diaryl-2-R-thieno[2,3-b]pyridine, pyrido[3’,2’:4,5]thieno[3,2-d]pyrimidine. During the reaction the interaction of malononitrile with hydrogen sulfide forms cyanothioacetamide, which is reactive with chalcone by Michael reaction. The corresponding adduct intramolecularly cyclizes into the substituted pyridine-2-thiolate N-methylmorpholinium. The latter can be alkylated in situ by alkyl halides into the aforementioned heterocyclic ring systems. The substituted 2-alkylsulphanil-pyridines with a labile hydrogen atom in the SCH2 fragment are capable to cyclize by Thorpe-Ziegler under alkaline conditions in direction to the intramolecular interaction with the cyano group of the pyridine ring vicinally located towards the methylensulphanil fragment. 3-Amino-6-(4-methoxyphenyl)-4-phenyl-2-cyanotieno[2,3-b]pyridine in refluxing in formamide easily forms 4-amino-7-(4-methoxyphenyl)-9-phenylpyrido[3’,2’:4,5]thieno[3,2-d]pyrimidine previously unknown. The composition and structure of the newly synthesized compounds have been confirmed by elemental analysis, infrared spectroscopy (IR), nuclear magnetic resonance of protons (1H NMR) and mass spectrometry.

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Published

2014-12-10

How to Cite

(1)
Dyachenko, I. V. The Multi-Component Condensation in the Synthesis of the Substituted 2-Alkylsulphanil-4,6-Diarilpyridine-3-Carbonitriles and Their Derivatives. J. Org. Pharm. Chem. 2014, 12, 49-54.

Issue

Vol. 12 No. 4(48) (2014)

Section

Original Researches

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