Synthesis of new 2-amino-4H-thiopyran derivatives via the one-pot reaction between 3,4-dihydro-3-((benzylamino)methylene)-4-thioxochromen-2-ones and alkyl-2-cyanoacetates in the presence of nano-ZnO catalysis

References

• Schneller S. Thiochromanones and related compounds. Adv Heterocycl Chem. 1975;18:59–97. doi: 10.1016/S0065-2725(08)60128-2
   Google Scholar
• Ilardi EA, Vitaku E, Njardarson JT. Data-mining for sulfur and fluorine: An evaluation of pharmaceuticals to reveal opportunities for drug design and discovery: miniperspective. J Med Chem. 2013;57:2832–2842. doi: 10.1021/jm401375q
   Google Scholar
• Martins P, Jesus J, Santos S, et al. Heterocyclic anticancer compounds: recent advances and the paradigm shift towards the use of nanomedicine’s tool box. Molecules. 2015;20:16852–16891. doi: 10.3390/molecules200916852
   Google Scholar
• Salat K, Moniczewski A, Librowski T. Nitrogen, oxygen or sulfur containing heterocyclic compounds as analgesic drugs used as modulators of the nitroxidative stress. Mini Rev Med Chem. 2013;13:335–352.
   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
• Rudorf W-D. Reactions of carbon disulfide with N-nucleophiles. J Sulfur Chem. 2007;28:295–339. doi: 10.1080/17415990701245107
   Google Scholar
• Gong Y-D, Lee T. Combinatorial syntheses of five-membered ring heterocycles using carbon disulfide and a solid support. J Comb Chem. 2010;12:393–409. doi: 10.1021/cc100049u
   Google Scholar
• Kondo T, Mitsudo T-a. Metal-catalyzed carbon- sulfur bond formation. Chem Rev. 2000;100:3205–3220. doi: 10.1021/cr9902749
   Google Scholar
• Nguyen TB, Tran MQ, Ermolenko L, et al. Three-component reaction between alkynes, elemental sulfur, and aliphatic amines: a general, straightforward, and atom economical approach to thioamides. Org Lett. 2013;16:310–313. doi: 10.1021/ol403345e
   Google Scholar
• Brown MJ, Carter PS, Fenwick AE, et al. The antimicrobial natural product chuangxinmycin and some synthetic analogues are potent and selective inhibitors of bacterial tryptophanyl tRNA synthetase. Bioorg Med Chem Lett. 2002;12:3171–3174. doi: 10.1016/S0960-894X(02)00604-2
   Google Scholar
• Rogier D, Carter J, Talley J. Dihydrobenzopyrans, dihydrobenzothiopyrans, and tetrahydroquinolines for the treatment of COX-2-mediated disorders. US Patents. 2004; 6,822,102.
   Google Scholar
• Hollick JJ, Golding BT, Hardcastle IR, et al. 2, 6-disubstituted pyran-4-one and thiopyran-4-one inhibitors of DNA-dependent protein kinase (DNA-PK). Bioorg Med Chem Lett. 2003;13:3083–3086. doi: 10.1016/S0960-894X(03)00652-8
   Google Scholar
• Rajabi M, Khalilzadeh MA, Mehrzad J. Antiproliferative activity of novel derivative of thiopyran on breast and colon cancer lines and DNA binding. DNA Cell Biol. 2012;31:128–134. doi: 10.1089/dna.2011.1291
   Google Scholar
• Quaglia W, Pigini M, Piergentili A, et al. Structure- activity relationships in 1, 4-benzodioxan-related compounds. 7. 1 selectivity of 4-phenylchroman analogues for α1- adrenoreceptor subtypes. J Med Chem. 2002;45:1633–1643. doi: 10.1021/jm011066n
   Google Scholar
• van Vliet LA, Rodenhuis N, Dijkstra D, et al. Synthesis and pharmacological evaluation of thiopyran analogues of the dopamine d3 receptor-selective agonist (4a r, 10b r)-(+)-trans-3, 4, 4a, 10b-tetrahydro-4-n-propyl-2 h, 5 h-[1] benzopyrano [4,3-b]-1, 4-oxazin-9-ol (pd 128907). J Med Chem. 2000;43:2871–2882. doi: 10.1021/jm0000113
   Google Scholar
• Dubey R, Singh VK, Sharma LK, et al. A convenient electro-catalyzed multicomponent synthesis of 4 H-thiopyran derivatives. New J Chem. 2017;41:7836–7839. doi: 10.1039/C7NJ01211J
   Google Scholar
• Mobinikhaledi A, Bodaghifard MA, Asadbegi S. A novel four-and pseudo-five-component reaction: unexpected efficient one-pot synthesis of 4H-thiopyran derivatives. Mol Divers. 2016;20:461–468. doi: 10.1007/s11030-015-9634-y
   Google Scholar
• Bodaghifard M, Mobinikhaledi A, Asadbegi S. Bis (4-pyridylamino) triazine-stabilized magnetite nanoparticles: preparation, characterization and application as a retrievable catalyst for the green synthesis of 4H-pyran, 4H-thiopyran and 1, 4-dihydropyridine derivatives. Appl Organometal Chem . 2017;31:e3557. doi: 10.1002/aoc.3557
   Google Scholar
• Aghaalizadeh T, Nasiri F. Serendipitous synthesis of 4-thioxochromen-2-one derivatives through the one-pot three-component reaction of primary amines, carbon disulfide, and 4-chlorocoumarin-3-carbaldehyde. J Sulfur Chem. 2017;38:635–644. doi: 10.1080/17415993.2017.1337769
   Google Scholar
• Ostrowska K, Dudek K, Musielak B. Synthesis of the new heterocyclic system 5, 6, 10b-triazaacephenanthrylene, a nitrogen analogue of aristolactams. Heterocycles. 2016;92:1307–1312. doi: 10.3987/COM-16-13480
   Google Scholar
• Mashrai A, Khanam H, Aljawfi RN. Biological synthesis of ZnO nanoparticles using C. albicans and studying their catalytic performance in the synthesis of steroidal pyrazolines. Arab J Chem. 2017;10:S1530–S1536. doi: 10.1016/j.arabjc.2013.05.004
   Google Scholar
• Zare A, Hasaninejad A, Zare ARM, et al. Zinc oxide as a new, highly efficient, green, and reusable catalyst for microwave-assisted michael addition of sulfonamides to α, β-unsaturated esters in ionic liquids. Can J Chem. 2007;85:438–444. doi: 10.1139/v07-050
   Google Scholar
• Zare A, Hasaninejad A, Khalafi-Nezhad A, et al. A green solventless protocol for michael addition of phthalimide and saccharin to acrylic acid esters in the presence of zinc oxide as a heterogeneous and reusable catalyst. Arkivoc. 2007;1:58–69.
   Google Scholar
• Tekale SU, Kauthale SS, Jadhav KM, Pawar RP. Nano-ZnO catalyzed green and efficient one-pot four-component synthesis of pyranopyrazoles. J Chem. 2013;2013;840954. doi: 10.1155/2013/840954
   Google Scholar
• Bhattacharyya P, Pradhan K, Paul S, et al. Nano crystalline ZnO catalyzed one pot multicomponent reaction for an easy access of fully decorated 4H-pyran scaffolds and its rearrangement to 2-pyridone nucleus in aqueous media. Tetrahedron Lett. 2012;53:4687–4691. doi: 10.1016/j.tetlet.2012.06.086
   Google Scholar
• Heravi MM, Daraie M. A novel and efficient five-component synthesis of pyrazole based pyrido [2, 3-d] pyrimidine-diones in water: A triply green synthesis. Molecules. 2016;21:441–423. doi: 10.3390/molecules21040441
   Google Scholar
• Ghasemzadeh MA, Safaei-Ghomi J. Synthesis and characterization of ZnO nanoparticles: application to one-pot synthesis of benzo [b][1, 5] diazepines. Cogent Chem. 2015;1:1095060. doi: 10.1080/23312009.2015.1095060
   Google Scholar
• Rao GD, Kaushik M, Halve A. An efficient synthesis of naphtha [1, 2-e] oxazinone and 14-substituted-14H-dibenzo [a,j] xanthene derivatives promoted by zinc oxide nanoparticle under thermal and solvent-free conditions. Tetrahedron Lett. 2012;53:2741–2744. doi: 10.1016/j.tetlet.2012.03.085
   Google Scholar