Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 42, 2012 - Issue 10
530
Views
11
CrossRef citations to date
0
Altmetric
Original Articles

Facile Synthesis of 6-Aryl-3-cyanopyridine-2-(1H)-thiones from Aryl Ketones

, , , , , & show all
Pages 1521-1531 | Received 07 Dec 2009, Published online: 25 Jan 2012

REFERENCES

  • For representative papers, see (a) Litvinov , V. P. ; Dotsenko , V. V. ; Krivokolysko , S. G. Thienopyridines: Synthesis, properties, and biological activity . Russ. Chem. Bull. 2005 , 54 , 864 – 904 ; (b) Krauze , A. ; Gērmane , S. ; Eberlinš , O. ; Šturms , I. ; Klusā , V. ; Duburs , G. Derivatives of 3-cyano-6-phenyl-4-(3’-pyridyl)-pyridine-2(1H)-thione and their neurotropic activity . Eur. J. Med. Chem. 1999 , 34 , 301 – 310 ; (c) Abdel-Fattah , A. M. ; Elsayed , M. M. Novel synthesis, reactions, and anticancer activities of 4,4′-benzene-1,4-diylbis (6-phenyl-2-thioxo-1,2-dihydropyridine-3-carbonitrile) . Curr. Org. Chem. 2009 , 13 , 1751 – 1757 .
  • For representative papers, see (a) Shirey , J. K. ; Xiang , Z. X. ; Orton , D. ; Brady , A. E. ; Johnson , K. A. ; Williams , R. ; Ayala , J. E. ; Rodriguez , A. L. ; Wess , J. ; Weaver , D. ; Niswender , C. M. ; Conn , P. J. An allosteric potentiator of M4 mAChR modulates hippocampal synaptic transmission . Nat. Chem. Biol. 2008 , 4 , 42 – 50 ; (b) Hayakawa , I. ; Shioya , R. ; Agatsuma , T. ; Furukawa , H. ; Sugano , Y. Thienopyridine and benzofuran derivatives as potent antitumor agents possessing different structure–activity relationships . Bioorg. Med. Chem. Lett. 2004 , 14 , 3411 – 3414 ; (c) Ho , Y. W. ; Wang , I. J. Heterocyclic monoazo dyes derived from 3-cyano-2-(1H)-pyridinethiones, part 1: 3-(Aryl or hetaryl)azothieno[2,3-b]pyridine derivatives . Dyes Pigm. 1995 , 29 , 117 – 129 ; (d) Debenham , J. S. ; Madsen-Duggan , C. B. ; Wang , J. Y. ; Tong , X. C. ; Lao , J. L. ; Fong , T. M. ; Schaeffer , M. T. ; Xiao , J. C. ; Huang , C. R. ; Shen , C. P. ; Sloan Stribling , D. ; Shearman , L. P. ; Strack , A. M. ; MacIntyre , D. E. ; Hale , J. J. ; Walsh , T. F. Pyridopyrimidine-based cannabinoid-1 receptor inverse agonists: Synthesis and biological evaluation . Bioorg. Med. Chem. Lett. 2009 , 19 , 2591 – 2594 ; (e) Morwick , T. ; Berry , A. ; Brickwood , J. ; Cardozo , M. ; Catron , K. ; DeTuri , M. ; Emeigh , J. ; Homon , C. ; Hrapchak , M. ; Jacober , S. ; Jakes , S. ; Kaplita , P. ; Kelly , T. A. ; Ksiazek , J. ; Liuzzi , M. ; Magolda , R. ; Mao , C. ; Marshall , D. ; McNeil , D. ; Prokopowicz , III , A. , Sarko , C. ; Scouten , E. ; Sledziona , C. ; Sun , S. ; Watrous , J. ; Wu , J. P. ; Cywin , C. L. Evolution of the thienopyridine class of inhibitors of IκB kinase-β, part I: Hit-to-lead strategies . J. Med. Chem. 2006 , 49 , 2898 – 2908 .
  • (a) Deng , X. Q. ; Wang , H. Y. ; Zhao , Y. L. ; Xiang , M. L. ; Jiang , P. D. ; Cao , Z. X. ; Zheng , Y. Z. ; Long , S. D. ; Yu , L. D. ; Wei , Y. Q. ; Yang , S. Y. Pharmacophore modelling and virtual screening for identification of new Aurora-A kinase inhibitors . Chem. Biol. Drug. Des. 2008 , 71 , 533 – 539 ; (b) Zeng , X. X. ; Zheng , R. L. ; Zhou , T. ; He , H. Y. ; Liu , J. Y. ; Zheng , Y. ; Tong , A. P. ; Xiang , M. L. ; Song , X. R. ; Yang , S. Y. ; Yu , L. T. ; Wei , Y. Q. ; Zhao , Y. L. ; Yang , L. Novel thienopyridine derivatives as specific anti-hepatocellular carcinoma (HCC) agents: The synthesis, preliminary structure–activity relationships, and in vitro biological evaluation . Bioorg. Med. Chem. Lett. 2010 , 20 , 6282 – 6285 .
  • Yakovlev , M. Y. ; Kadushkin , A. V. ; Granik , V. G. Synthesis of new pyrrolo- and thieno[2,3-b]pyridine derivatives by the Thorpe–Ziegler reaction . Khim. Farm. Zh. 1996 , 30 , 36 – 38 .
  • (a) Rodinovskaya , L. A. ; Sharanin , Y. A. ; Shestopalov , A. ; Litvinov , V. P. Cyclization reactions of nitriles, 29: Regioselective synthesis and properties of 6-aryl-3-cyano-2(1H)-pyridinethiones and the corresponding selenones and their characteristics . Khimiya Geterotsiklicheskikh Soedinenii 1988 , 6 , 805 – 812 ; (b) Maryashova , S. I. ; Salamandra , L. K. ; Fedorov , A. E. ; Rodinovskaya , L. A. ; Shestopalov , A. M. ; Semenov , V. V. Regioselective synthesis and properties of 3-cyano-6-thienyl-2(1H)-pyridinethiones . Russ. Chem. Bull. 1998 , 47 , 357 – 360 .
  • Li , M. ; Guo , W. S. ; Wen , L. R. ; Yang , H. Z. Synthesis of enaminones and their utility in organic synthesis . Chin. J. Org. Chem. 2006 , 26 , 1192 – 1207 .
  • Chunikhin , K. S. ; Rodinovskaya , L. A. ; Shestopalov , A. M. Synthesis of 6-substituted 3-cyano-5-nitropyridine-2(1H)-thiones . Russ. Chem. Bull. 2003 , 52 , 447 – 450 .
  • For examples of condensation of enaminones with cyanthioacetamide, see (a) Abdelhamid , A. O. ; Al-Atoom , A. A. Reactions with hydrazonoyl halides 45: Synthesis of some new triazolino[4,3-a]pyrimidines, pyrazolo[3,4-d]pyridazines, isoxazolo[3,4-d]pyridazines, and thieno[2,3-b]pyridines. Synth. Commun. 2006, 36, 97–110; (b) Abdelhamid , A. O. ; Alkhodshi , M. M. Reactions of hydrazonoyl halides 43 [1]: Synthesis of some new 2,3-dihydro-1,3,4-thiadiazoles, pyrazoles, pyrazolo[3,4-d]pyridazines, thieno[2,3-b]pyridines, pyrimidino[4’,5':4,5]thieno [2,3-b] pyridines and pyrrolo[3,4-b]pyrazoles. J. Heterocycl. Chem. 2005, 42, 527–533; (c) Hussein , A. M. ; Ishak , E. A. ; Atalla , A. A. ; Hafiz , S. A. ; Elnagdi , M. H. Phenylacetone as building blocks in heterocyclic synthesis: Synthesis of polyfunctionally substituted pyridines, and fused pyridines. Phosphorus Sulfur Silicon Relat. Elem. 2007, 182, 2897–2917; (d) Balkis , A. S. ; Ahmed , E. M. ; Safwat , A. R. ; Hilmy , E. M. Enaminones in heterocyclic synthesis: Synthesis and chemical reactivity of 3-anilino-1-substituted-2-propene-1-one. J. Heterocycl. Chem. 2005, 42, 563–566; (e) Abdelkhalika , M. M. ; Eltoukhya , A. M. ; Agamya , S. M. ; Elnagdi , M. H. Enaminones as building blocks in heterocyclic synthesis: new syntheses of nicotinic acid and thienopyridine derivatives. J. Heterocycl. Chem. 2004, 41, 431–434; (f) Al-Omran , F. ; Al-Awadi , N. ; El-Khair , A. A. ; Elnagdi , M. H. Synthesis of new aryl and heteroaromatic substituted pyridines, pyrazoles, pyrimidines, and pyrazolo [3,4-d] pyridazines. Org. Prep. Proced. Int. 1997, 29, 285–292.
  • Elkareem , G. ; Mohamed , A. M. ; Abdelhamid , A. O. A new route for the synthesis of several new 4-benzoylpyrazoles, thieno[2,3-b]pyridines, and pyrimido[4’,5':4,5] thieno [2,3-b]pyridines . Afinidad 2004 , 61 , 427 – 432 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.