Facile and rapid synthesis of piperidinium-6-amino-4-aryl-3, 5-dicyano-1,4-dihydropyridine-2-thiolate

References

• Gore RP, Rajput AP. A review on recent progress in multicomponent reactions of pyrimidine synthesis. Drug Invent Today. 2013;5:148–152. doi: 10.1016/j.dit.2013.05.010
   Google Scholar
• Rotstein BH, Zaretsky S, Rai V, et al. Small heterocycles in multicomponent reactions. Chem Rev. 2014;114:8323–8359. doi: 10.1021/cr400615v
   Google Scholar
• Bayat M, Hosseini FS, Notash B. Stereoselective synthesis of indenone-fused heterocyclic compounds via a one-pot four-component reaction. Tetrahedron. 2017;73:1196–1204. doi: 10.1016/j.tet.2017.01.024
   Google Scholar
• Biggs-Houck JE, Younai A, Shaw JT. Recent advances in multicomponent reactions for diversity-oriented synthesis. Curr Opin Chem Biol. 2010;14:371–382. doi: 10.1016/j.cbpa.2010.03.003
   Google Scholar
• Movassaghi M, Hill MD, Ahmad OK. Direct synthesis of pyridine derivatives. J Am Chem Soc. 2007;129:10096–10097. doi: 10.1021/ja073912a
   Google Scholar
• Almeida MVD, Souza MVN, Barbosa NR, et al. Synthesis and antimicrobial activity of pyridine derivatives substituted at C-2 and C-6 positions. Lett Drug Des Discov. 2007;4:149–153. doi: 10.2174/157018007779422514
   Google Scholar
• Sharma VK, Singh SK. Synthesis, utility and medicinal importance of 1,2- & 1,4-dihydropyridines. RSC Adv. 2017;7:2682–2732. doi: 10.1039/C6RA24823C
   Google Scholar
• Chaubey A, Pandeya SN. Pyridine” a versatile nucleuse in pharmaceutical field. Asian J Pharm Clin Res. 2011;4:5–8.
   Google Scholar
• Al-Issa SA. Synthesis of a new series of pyridine and fused pyridine derivatives. Molecules. 2012;17:10902–10915. doi: 10.3390/molecules170910902
   Google Scholar
• Rashid H, Shahzad A, Gul Z, et al. Facile synthesis, characterization and DFT calculations of 2-acetyl pyridine derivatives. Quim Nova. 2017;40:902–907.
   Google Scholar
• Mao ZY, Liao XY, Wang HS, et al. Acid-catalyzed tandem reaction for the synthesis of pyridine derivatives via C=C/C(sp3)–N bond cleavage of enones and primary amines. RSC Adv. 2017;7:13123–13129. doi: 10.1039/C7RA00780A
   Google Scholar
• Comins DL, Higuchi K, Young DW. Dihydropyridine preparation and application in the synthesis of pyridine derivatives. Adv Heterocycl Chem. 2013;110:175–235. doi: 10.1016/B978-0-12-408100-0.00006-9
   Google Scholar
• Dyachenko IV. New multicomponent synthesis of functionally substituted partially hydrogenated thiazolo[3,2-а]quinolone and thiazolo[3,2-а]pyridine. Russ J Org Chem. 2015;51:1584–1586. doi: 10.1134/S1070428015110111
   Google Scholar
• Helal MH, El-Awdan SA, Salem MA, et al. Synthesis, biological evaluation and molecular modeling of novel series of pyridine derivatives as anticancer, anti-inflammatory and analgesic agents. Spectrochim Acta A Mol Biomol Spectrosc. 2015;135:764–773. doi: 10.1016/j.saa.2014.06.145
   Google Scholar
• Hill MD. Recent strategies for the synthesis of pyridine derivatives. Chem Eur J. 2010;16:12052–12062. doi: 10.1002/chem.201001100
   Google Scholar
• Podolan G, Hettmanczyk L, Hommes P, et al. Synthesis and (spectro)electrochemistry of ferrocenyl-substituted pyridine derivatives. Eur J Org Chem. 2015;2015:7317–7323. doi: 10.1002/ejoc.201501163
   Google Scholar
• Poorfreidoni A, Ranjbar-Karim R. Synthesis of substituted imidazopyridines from perfluorinated pyridine derivatives. Tetrahedron Lett. 2016;57:5781–5783. doi: 10.1016/j.tetlet.2016.11.045
   Google Scholar
• Dash J, Trawny D, Rabe JP, et al. C3-symmetric pyridine and bipyridine derivatives: simple preparation by cyclocondensation and 2D self-assembly at a solution–graphite interface. Synlett. 2015;26:A–D.
   Google Scholar
• Sharif M, Shoaib K, Ahmed S, et al. Synthesis of functionalised fluorinated pyridine derivatives by site-selective Suzuki-Miyaura cross-coupling reactions of halogenated pyridines. Z Naturforsch. 2017;72:263–279. doi: 10.1515/znb-2016-0213
   Google Scholar
• Trawny D, Kunz V, Reissig HU. Modular syntheses of star-shaped pyridine, bipyridine, and terpyridine derivatives by employing sonogashira reactions. Eur J Org Chem. 2014;2014:6295–6302. doi: 10.1002/ejoc.201402778
   Google Scholar
• Abbas I, Gomha S, Elaasser M, et al. Synthesis and biological evaluation of new pyridines containing imidazole moiety as antimicrobial and anticancer agents. Turk J Chem. 2015;39:334–346. doi: 10.3906/kim-1410-25
   Google Scholar
• Khalifa NM, Al-Omar MA, Nossier ES. Synthesis and characterization of some novel 1,3-diaryl pyrazole bearing 2-oxopyridine-3,5-dicarbonitrile derivatives. Russ J Gen Chem. 2017;87:846–849. doi: 10.1134/S1070363217040296
   Google Scholar
• Pasha MA, Datta B. Mechanochemistry: an efficient method of solvent-free synthesis of 3-amino-2,4-dicarbonitrile-5-methylbiphenyls. J Saudi Chem soc. 2014;18:47–51. doi: 10.1016/j.jscs.2011.05.012
   Google Scholar
• Cui Y, Floreancig PE. Synthesis of sulfur-containing heterocycles through oxidative carbon hydrogen bond functionalization. Org Lett. 2012;14:1720–1723. doi: 10.1021/ol3002877
   Google Scholar
• Kvasnica M, Urban M, Dickinson NJ, et al. Pentacyclic triterpenoids with nitrogen- and sulfurcontaining heterocycles: synthesis and medicinal significance. Nat Prod Rep. 2015;32:1303–1330. doi: 10.1039/C5NP00015G
   Google Scholar
• Shrivastava K, Purohit S, Singhal S. Studies on nitrogen and sulphur containing heterocyclic compound: 1,3,4-thiadiazole. Asian J Biomed Pharm. 2013;3:6–23.
   Google Scholar
• Joshi H, Shah N, Sakar D, et al. One pot synthesis and biological evaluation of some new pyridine-3,5-dicarbonitrile derivatives. ChemistrySelect. 2018;3:3374–3378. doi: 10.1002/slct.201702116
   Google Scholar
• Desai UV, Kulkarni MA, Pandit KS, et al. A simple, economical, and environmentally benign protocol for the synthesis of 2-amino-3,5-dicarbonitrile-6-sulfanylpyridines at ambient temperature. Green Chem Lett Rev. 2014;3:228–235. doi: 10.1080/17518253.2014.925144
   Google Scholar
• Niknam K, Hosseini AR. Synthesis of 2-amino-3,5-dicarbonitrile-6-thiopyridines using silica-bonded N-propyldiethylenetriamine as a heterogeneous solid base catalyst. Org Chem Res. 2017;3:16–24.
   Google Scholar
• Dyachenko VD, Dyachenko VI, Nenajdenko VG. Cyanothioacetamide: a polyfunctional reagent with broad synthetic utility. Russ Chem Rev. 2018;87:1–27. doi: 10.1070/RCR4760
   Google Scholar
• Dyachenko VD, Krivokolysko SG, Litvinov VP. Synthesis and transformations of 6-amino-3,5-dicyano-4-ethylpyridine-2(1H)-thione. Chem Heterocycl Compd. 1996;32:942–946. doi: 10.1007/BF01176971
   Google Scholar
• Rodinovskaya LA, Shestopalov AM, Nesterov VN. Stereoselective synthesis and structure of 3,4-trans-6-amino-4-aryl-3-carbamoyl-5-cyano-1,2,3,4-tetrahydropyridin-2-(1H)-thiones. Chem Heterocycl Compd. 1996;32:1182–1188. doi: 10.1007/BF01169231
   Google Scholar
• Abbas HAS, El-Sayed WA, Fathy NM. Synthesis and antitumor activity of new dihydropyridine thioglycosides and their corresponding dehydrogenated forms. Eur J Med Chem. 2010;45:973–982. doi: 10.1016/j.ejmech.2009.11.039
   Google Scholar