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

I. V. Dyachenko

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.


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

References


Tietze L. F., Brashe G., Gerike K. M. Domino Reactions in organic synthesis, Weiheim, WILEY-VCH, 2006, 631p.

Abdel-Latif F. F., Shaker R. M. Heterocycle synthesis through one-flask multicomponent condensation of aldehydes and Retetones, Topics in Heterocyclic systems – synthesis, reactions and properties, 1996, pp.87-101.

Dyachenko V. D. Unexpected compounds in the “Pyridine club”, International conference chemistry of nitrogen comfaining heterocycles “CNCH – 2003”, Kharkiv, 2003, p.23.

Selected methods for synthesis and modification of heterocycles, edited by V. G. Kartsev, Moscow, IBS PRESS, 2002, p.488.

Ugi I. The preparative advantages of the multicomponent reactions, tezisi dokladov III Vseross. simpoziuma po organicheskoi chimii “Strategia i taktika organicheskogo sinteza”, Yaroslavl, 2001. (Abstracts 3 Russian Symposium on Organic Chemistry “Strategy and Tactics of Organic Synthesis”, Yaroslavl, 2001), p.2.

Krause A., Germane S., Eberlins O., Sturms I., Klusa V., Duburs G. Eur. J. Med. Chem., 1999, Vol. 34, pp.301-310.

Hussein A. M., Abu-Shanab F. A., Ishak E. A. Phosphorus. Sulfur, Silicon, Relat. Elem., 2000, Vol. 159, pp.55-68.

Bakhite E. A., Abdel-Rahman A. E., Al-Taifi E. A. Phosphorus. Sulfur, Silicon, Relat. Elem., 2004, Vol. 179, pp.513-520.

Mermerian A. H., Case A., Stein R. L., Cuny G. D. Bioorg. Med. Chem. Lett., 2007, pp.3729-3732.

Abdel-Rahman A. E., Bakhite E. A., Mohamed O. S., Thabet E. A. Phosphorus. Sulfur, Silicon, Relat. Elem., 2003, Vol. 178, pp.89-106.

Dyachenko V. D., Chernega A. N. Chem. Heterocycl. Compd., 2005, Vol. 41, pp.1499-1506.

Abdel-Fattah A. M., Elneairy M. A. A., Attaby F. A. Phosphorus. Sulfur, Silicon, Relat. Elem., 2008, Vol. 183, pp.1592-1614.

Attaby F. A., Eldin S. M., Elneairy M. A. A., El-Louh A. K. K. Phosphorus. Sulfur, Silicon, Relat. Elem., 2004, Vol. 178, pp.2205-2220.

Abdulla M. M., Monatsh. Chem., 2008, B. 139, S.69-76.

Attaby F. A. Phosphorus. Sulfur, Silicon, Relat. Elem., 1998, Vol. 139, pp.1-12.

Vieweg H., Hanfeld V., Leistner S., Wagner G. Pharmazie, 1989, B. 44, S.639-640.


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

Abbreviated key title: Ž. org. farm. hìm.

ISSN 2518-1548 (Online), ISSN 2308-8303 (Print)