Chitosan functionalized by citric acid: an efficient catalyst for one-pot synthesis of 2,4-diamino-5H-[1]benzopyrano[2,3-b]pyridine-3-carbonitriles 5-(arylthio) or 5-[(arylmethyl)thio] substituted

References

• Unangst PC, Capiris T, Connor DT, et al. Chromeno[3,4-c]pyridin-5-ones: selective human dopamine D4 receptor antagonists as potential antipsychotic agents. J Med Chem. 1997;40:2688–2693. doi: 10.1021/jm970170v
   PubMed Web of Science ®Google Scholar
• Hosni HM, Abdulla MM. Anti-inflammatory and analgesic activities of some newly synthesized pyridinecarbonitrile and benzopyranopyridine derivatives. Acta Pharm (Zagreb, Croatia). 2008;58:175–186.
   PubMed Web of Science ®Google Scholar
• Goto K, Terasawa M, Maruyama Y. Anti-allergic activities of a new benzopyranopyridine derivative Y-12,141 in rats. Int Arch Allergy Appl Immunol. 1979;59:13–19. doi: 10.1159/000232234
   PubMedGoogle Scholar
• Ukawa K, Ishiguro T, Kuriki H, et al. Synthesis of the metabolites and degradation products of 2-amino-7-isopropyl-5-oxo-5H-[1] benzopyrano [2, 3-b] pyridine-3-carboxylic acid (Amoxanox). Chem Pharm Bull. 1985;33:4432–4437. doi: 10.1248/cpb.33.4432
   PubMed Web of Science ®Google Scholar
• Frolova LV, Malik I, Uglinskii PY, et al. Multicomponent synthesis of 2,3-dihydrochromeno[4,3-d]pyrazolo[3,4-b]pyridine-1,6-diones: a novel heterocyclic scaffold with antibacterial activity. Tetrahedron Lett. 2011;52:6643–6645. doi: 10.1016/j.tetlet.2011.10.012
   PubMed Web of Science ®Google Scholar
• Khan IA, Kulkarni MV, Gopal M, et al. Synthesis and biological evaluation of novel angularly fused polycyclic coumarins. Bioorg Med Chem Lett. 2005;15:3584–3587. doi: 10.1016/j.bmcl.2005.05.063
   PubMed Web of Science ®Google Scholar
• Pars HG, Granchelli FE, Razdan RK, et al. Drugs derived from cannabinoids. 1. Nitrogen analogs, benzopyranopyridines and benzopyranopyrroles. J Med Chem. 1976;19:445–454. doi: 10.1021/jm00226a001
   PubMed Web of Science ®Google Scholar
• Núñez-Vergara LJ, Squella JA, Navarrete-Encina PA, et al. Chromenopyridines: promising scaffolds for medicinal and biological chemistry. Curr Med Chem. 2011;18:4761–4785. doi: 10.2174/092986711797535272
   PubMed Web of Science ®Google Scholar
• Mishra S, Ghosh R. K2CO3-mediated, one-pot, multicomponent synthesis of medicinally potent pyridine and chromeno[2,3-b]pyridine scaffolds. Synth Commun. 2012;42:2229–2244. doi: 10.1080/00397911.2011.555284
   Web of Science ®Google Scholar
• Evdokimov NM, Kireev AS, Yakovenko AA, et al. Convenient one-step synthesis of a medicinally relevant benzopyranopyridine system. Tetrahedron Lett. 2006;47:9309–9312. doi: 10.1016/j.tetlet.2006.10.110
   PubMed Web of Science ®Google Scholar
• Evdokimov NM, Kireev AS, Yakovenko AA, et al. One-step synthesis of heterocyclic privileged medicinal scaffolds by a multicomponent reaction of malononitrile with aldehydes and thiols. J Org Chem. 2007;72:3443–3453. doi: 10.1021/jo070114u
   PubMed Web of Science ®Google Scholar
• Osyanin VA, Osipov DV, Klimochkin YV. Convenient one-step synthesis of 4-unsubstituted 2-amino-4H-chromene-2-carbonitriles and 5-unsubstituted 5H-chromeno[2,3-b]pyridine-3-carbonitriles from quaternary ammonium salts. Tetrahedron. 2012;68:5612–5618. doi: 10.1016/j.tet.2012.04.065
   Web of Science ®Google Scholar
• Safaei-Ghomi J, Kiani M, Ziarati A, et al. Highly efficient synthesis of benzopyranopyridines via ZrP2O7 nanoparticles catalyzed multicomponent reactions of salicylaldehydes with malononitrile and thiols. J Sulfur Chem. 2014;35:450–457. doi: 10.1080/17415993.2014.913291
   Web of Science ®Google Scholar
• Chtchigrovsky M, Primo A, Gonzalez P, et al. Functionalized chitosan as a green, recyclable, biopolymer-supported catalyst for the [3 + 2] Huisgen cycloaddition. Angew Chem Int Ed. 2009;48:5916–5920. doi: 10.1002/anie.200901309
   PubMed Web of Science ®Google Scholar
• Zhao Y, Tian JS, Qi XH, et al. Quaternary ammonium salt-functionalized chitosan: an easily recyclable catalyst for efficient synthesis of cyclic carbonates from epoxides and carbon dioxide. J Mol Catal A: Chem. 2007;271:284–289. doi: 10.1016/j.molcata.2007.03.047
   Web of Science ®Google Scholar
• Sun J, Wang J, Cheng W, et al. Chitosan functionalized ionic liquid as a recyclable biopolymer-supported catalyst for cycloaddition of CO2. Green Chem. 2012;14:654–660. doi: 10.1039/c2gc16335g
   Web of Science ®Google Scholar
• Sudheesh N, Sharma SK, Shukla RS. Chitosan as an eco-friendly solid base catalyst for the solvent-free synthesis of jasminaldehyde. J Mol Catal A: Chem. 2010;321:77–82. doi: 10.1016/j.molcata.2010.02.005
   Web of Science ®Google Scholar
• El Kadib A. Chitosan as a sustainable organocatalyst: a concise overview. ChemSusChem. 2015;8:217–244. doi: 10.1002/cssc.201402718
   PubMed Web of Science ®Google Scholar
• Guibal E. Heterogeneous catalysis on chitosan-based materials: a review. Prog Polym Sci. 2005;30:71–109. doi: 10.1016/j.progpolymsci.2004.12.001
   Web of Science ®Google Scholar
• El Kadib A, Molvinger K, Guimon C, et al. Design of stable nanoporous hybrid chitosan/titania as cooperative bifunctional catalysts. Chem Mater. 2008;20:2198–2204. doi: 10.1021/cm800080s
   Web of Science ®Google Scholar
• Caetano CS, Caiado M, Farinha J, et al. Esterification of free fatty acids over chitosan with sulfonic acid groups. Chem Eng J. 2013;230:567–572. doi: 10.1016/j.cej.2013.06.050
   Web of Science ®Google Scholar
• Madanifar Z, Maghsoodlou MT, Kangani M, et al. Citric acid, a green catalyst for the one-pot, multi-component synthesis of highly substituted piperidines. Res Chem Intermed. 2015;41:9863–9869. doi: 10.1007/s11164-015-1993-6
   Web of Science ®Google Scholar
• Labet M, Thielemans W. Citric acid as a benign alternative to metal catalysts for the production of cellulose-grafted-polycaprolactone copolymers. Polym Chem. 2012;3:679–684. doi: 10.1039/c2py00493c
   Web of Science ®Google Scholar
• Ding QS, Zhang JL, Chen JX, et al. Tandem synthesis of 2,3-dihydroquinazolin-4(1H)-ones on grinding under solvent-free conditions. J Heterocycl Chem. 2012;49:375–380. doi: 10.1002/jhet.759
   Web of Science ®Google Scholar
• Bagheri M, Younesi H, Hajati S, et al. Application of chitosan-citric acid nanoparticles for removal of chromium (VI). Int J Biol Macromol. 2015;80:431–444. doi: 10.1016/j.ijbiomac.2015.07.022
   PubMed Web of Science ®Google Scholar
• Safaei-Ghomi J, Heidari-Baghbahadorani E, Shahbazi-Alavi H, et al. A comparative study of the catalytic activity of nanosized oxides in the one-pot synthesis of highly substituted dihydropyridines. RSC Adv. 2015;5:18145–18152. doi: 10.1039/C4RA14557G
   Web of Science ®Google Scholar
• Mahesh R, Dhar AK, Tvnv TS, et al. Citric acid: an efficient and green catalyst for rapid one pot synthesis of quinoxaline derivatives at room temperature. Chin Chem Lett. 2011;22:389–392. doi: 10.1016/j.cclet.2010.11.002
   Web of Science ®Google Scholar
• Zolfigol MA, Mokhlesi M, Farahmand S. Application of citric acid as highly efficient and green organocatalyst for multi-component synthesis of indazolo[2,1-b]phthalazine-triones. J Iran Chem Soc. 2013;10:577–581. doi: 10.1007/s13738-012-0193-1
   Web of Science ®Google Scholar
• Dekamin MG, Azimoshan M, Ramezani L. Chitosan: a highly efficient renewable and recoverable bio-polymer catalyst for the expeditious synthesis of α-amino nitriles and imines under mild conditions. Green Chem. 2013;15:811–820. doi: 10.1039/c3gc36901c
   Web of Science ®Google Scholar
• Safari J, Azizi F, Sadeghi M. Chitosan nanoparticles as a green and renewable catalyst in the synthesis of 1,4-dihydropyridine under solvent-free conditions. New J Chem. 2015;39:1905–1909. doi: 10.1039/C4NJ01730G
   Web of Science ®Google Scholar
• Safari J, Abedi-Jazini Z, Zarnegar Z, et al. Nanochitosan: a biopolymer catalytic system for the synthesis of 2-aminothiazoles. Catal Commun. 2016;77:108–112. doi: 10.1016/j.catcom.2016.01.007
   Web of Science ®Google Scholar
• Ling Z, Wang G, Zhang M, et al. Boric acid-mediated B,N-codoped chitosan-derived porous carbons with a high surface area and greatly improved supercapacitor performance. Nanoscale. 2015;7:5120–5125. doi: 10.1039/C5NR00081E
   PubMed Web of Science ®Google Scholar
• Boddu VM, Abburi K, Talbott JL, et al. Removal of arsenic(III) and arsenic(V) from aqueous medium using chitosan-coated biosorbent. Water Res. 2008;42:633–642. doi: 10.1016/j.watres.2007.08.014
   PubMed Web of Science ®Google Scholar
• Tang CL, Lv LP, Xu YT, et al. A novel solid-acid catalyst using sulfonated crosslinked chitosan resin. Chem Biochem Eng Q. 2016;30:227–236. doi: 10.15255/CABEQ.2015.2279
   Web of Science ®Google Scholar