An appropriate one-pot synthesis of 3,4-dihydropyrano[c]chromenes and 6-amino-5-cyano-4-aryl-2-methyl-4H-pyrans with thiourea dioxide as an efficient, reusable organic catalyst in aqueous mediumFootnote

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References

• J.ZhuH.BienaymeMulticomponent Reactions2005Wiley-VCHWeinheim
   Google Scholar
• J.SafariZ.ZarnegarM.HeydarianPractical, ecofriendly, and highly efficient synthesis of 2-amino-4H-chromenes using nanocrystalline MgO as a reusable heterogeneous catalyst in aqueous mediaJ. Taibah Univ. Sci.720131725
   Google Scholar
• L.BonsignoreG.LoyD.SecciA.CalignanoSynthesis and pharmacological activity of 2-oxo-(2H) 1-benzopyran-3-carboxamide derivativesEur. J. Med. Chem.281993517520
   Web of Science ®Google Scholar
• G.CingolaniF.GualtieriM.PiginiNotes. Researches in the field of antiviral compounds. Mannich bases of 3-hydroxycoumarinJ. Med. Chem.121969531532
   PubMed Web of Science ®Google Scholar
• J.Y.C.WuW.F.FongJ.X.ZhangC.H.LeungH.L.KwongM.S.YangD.LiH.Y.CheungReversal of multidrug resistance in cancer cells by pyranocoumarins isolated from Radix peucedaniEur. J. Pharmacol.4732003917
   PubMed Web of Science ®Google Scholar
• F.W.PerrellaS.F.ChenD.L.BehrensR.F.KaltenbachIIIS.P.SeitzPhospholipase C inhibitors: a new class of agentsJ. Med. Chem.37199422322237
   PubMed Web of Science ®Google Scholar
• N.R.EmmadiK.AtmakurG.K.ChityalS.PombalaJ.B.NanuboluSynthesis and cytotoxicity evaluation of highly functionalized pyranochromenes and pyranopyransBioorg. Med. Chem. Lett.22201272617264
   PubMed Web of Science ®Google Scholar
• Y.KashmanK.R.GustafsonR.W.FullerJ.H.CardellinaJ.B.McmahonM.J.CurrensR.W.BuckheitS.H.HughesG.M.CraggM.R.BoydHIV inhibitory natural products. Part 7. The calanolides, a novel HIV-inhibitory class of coumarin derivatives from the tropical rainforest tree, Calophyllum lanigerumJ. Med. Chem.35199227352743
   PubMed Web of Science ®Google Scholar
• A.D.PatilA.J.FreyerD.S.EgglestonR.C.HaltiwangerM.F.BeanP.B.TaylorM.J.CaranfaA.L.BreenH.R.BartusThe inophyllums, novel inhibitors of HIV-1 reverse transcriptase isolated from the Malaysian tree, Calophyllum inophyllum Linn.J. Med. Chem.36199341314138
   PubMed Web of Science ®Google Scholar
• D.C.MungraM.P.PatelD.P.RajaniR.G.PatelSynthesis and identification of β-aryloxyquinolines and their pyrano[3,2-c]chromene derivatives as a new class of antimicrobial and antituberculosis agentsEur. J. Med. Chem.46201141924200
   PubMed Web of Science ®Google Scholar
• K.NiknamA.JamaliSilica-bonded N-propylpiperazine sodium n-propionate as recyclable basic catalyst for synthesis of 3,4-dihydropyrano[c]chromene derivatives and biscoumarinsChin. J. Catal.33201218401849
   Web of Science ®Google Scholar
• H.J.WangJ.LuZ.H.ZhangHighly efficient three component, one-pot synthesis of dihydropyrano[3,2-c]chromene derivativesMonatsh. Chem.141201011071112
   Web of Science ®Google Scholar
• J.M.KhuranaS.KumarTetrabutylammonium bromide (TBAB): a neutral and efficient catalyst for the synthesis of biscoumarin and 3,4-dihydropyrano[c]chromene derivatives in water and solvent-free conditionsTetrahedron Lett.50200941254127
   Web of Science ®Google Scholar
• J.M.KhuranaB.NandP.SalujaDBU: a highly efficient catalyst for one-pot synthesis of substituted 3,4-dihydropyrano[3,2-c]chromenes, dihydropyrano[4,3-b]pyranes, 2-amino-4H-benzo[h]chromenes and 2-amino-4H-benzo[g]chromenes in aqueous mediumTetrahedron66201056375641
   Web of Science ®Google Scholar
• A.T.KhanM.LalS.AliM.M.KhanOne-pot three-component reaction for the synthesis of pyran annulated heterocyclic compounds using DMAP as a catalystTetrahedron Lett.52201153275332
   Web of Science ®Google Scholar
• S.AbdolmohammadiS.BalalaieNovel and efficient catalysts for the one-pot synthesis of 3,4-dihydropyrano[c]chromene derivatives in aqueous mediaTetrahedron Lett.48200732993303
   Web of Science ®Google Scholar
• H.MehrabiM.Kazemi-MirekiCuO nanoparticles: an efficient and recyclable nanocatalyst for the rapid and green synthesis of 3,4-dihydropyrano[c]chromenesChin. Chem. Lett.22201114191422
   Web of Science ®Google Scholar
• H.MehrabiH.AbusaidiSynthesis of biscoumarin and 3,4-dihydropyrano[c]chromene derivatives catalysed by sodium dodecyl sulfate (SDS) in neat waterJ. Iran. Chem. Soc.72010890894
   Web of Science ®Google Scholar
• J.ZhengY.LiBasic ionic liquid-catalyzed multicomponent synthesis of tetrahydrobenzo[b]pyrans and pyrano[c]chromenesMendeleev Commun.212011280281
   Web of Science ®Google Scholar
• H.NagabhushanaS.S.SaundalkarL.MuralidharB.M.NagabhushanaC.R.GirijaD.NagarajaM.A.PashaV.P.Jayashankaraα-Fe2O3 nanoparticles: an efficient, inexpensive catalyst for the one-pot preparation of 3,4-dihydropyrano[c]chromenesChin. Chem. Lett.222011143146
   Web of Science ®Google Scholar
• K.NiknamA.PiranSilica-grafted ionic liquids as recyclable catalysts for the synthesis of 3,4-dihydropyrano[c]chromenes and pyrano[2,3-c]pyrazolesGreen Sustain. Chem.3201318
   Google Scholar
• Z.VafajooH.VeisiM.T.MaghsoodlouH.AhmadianElectrocatalytic multicomponent assembling of aldehydes, 4-hydroxycoumarin and malononitrile: an efficient approach to 2-amino-5-oxo-4,5-dihydropyrano [3,2-c]chromene-3-carbonitrile derivativesC. R. Chim.172014301304
   Web of Science ®Google Scholar
• G.BrahmachariB.BanerjeeFacile and one-pot access to diverse and densely functionalized 2-amino-3-cyano-4H-pyrans and pyran-annulated heterocyclic scaffolds via an eco-friendly multicomponent reaction at room temperature using urea as a novel organo-catalystSustain. Chem. Eng.22014411422
   Web of Science ®Google Scholar
• H.KiyaniF.GhorbaniPotassium phthalimide: an efficient and simple organocatalyst for the one-pot synthesis of dihydropyrano[3,2-c]chromenes in aqueous mediaRes. Chem. Intermed.201310.1007/s11164-013-1508-2
   Web of Science ®Google Scholar
• Y.WangJ.LuoT.XingZ.LiuSynthesis of a novel piperidine-functionalized poly(ethylene glycol) bridged dicationic ionic liquid and its application in one-pot synthesis of substituted 2-amino-2-chromenes and 3,4-dihydropyrano[3,2-c]chromenes in aqueous mediaMonatsh. Chem.144201318711876
   Web of Science ®Google Scholar
• J.P.PatelJ.R.AvalaniD.K.RavalPolymer supported sulphanilic acid: a highly efficient and recyclable green heterogeneous catalyst for the construction of 4,5-dihydropyrano[3,2-c] chromenes under solvent-free conditionsJ. Chem. Sci.1252013531536
   Web of Science ®Google Scholar
• D.S.PatelJ.R.AvalaniD.K.RavalOne-pot solvent-free rapid and green synthesis of 3,4-dihydropyrano[c]chromenes using grindstone chemistryJ. Saudi Chem. Soc.201310.1016/j.jscs.2012.12.008
   Web of Science ®Google Scholar
• S.KanakarajuB.PrasannaS.BasavojuG.V.P.ChandramouliAmmonium acetate catalyzed an efficient one-pot three component synthesis of pyrano[3,2-c]chromene derivativesArab. J. Chem.201310.1016/j.arabjc.2013.10.014
   Web of Science ®Google Scholar
• H.R.ShaterianF.RigiNew applications of cellulose-SO3H as a bio-supported and biodegradable catalyst for the one-pot synthesis of some three-component reactionsRes. Chem. Intermed.201310.1007/s11164-013-1145-9
   Web of Science ®Google Scholar
• M.M.HeraviB.A.JaniF.DerikvandF.F.BamoharramH.A.OskooieThree component, one-pot synthesis of dihydropyrano[3,2-c]chromene derivatives in the presence of H6P2W18O62·18H2O as a green and recyclable catalystCatal. Commun.102008272275
   Web of Science ®Google Scholar
• S.V.MakarovRecent trends in the chemistry of sulfur-containing reducing agentsRuss. Chem. Rev.702001885895
   Google Scholar
• S.VermaS.KumarS.L.JainB.SainThiourea dioxide promoted efficient organocatalytic one-pot synthesis of a library of novel heterocyclic compoundsOrg. Biomol. Chem.9201169436948
   PubMed Web of Science ®Google Scholar
• S.KumarS.L.JainB.SainThiourea dioxide promoted cobalt-catalyzed hydrolysis of imines: dual activation via organocatalysis and metal catalysisRSC Adv.22012s789s791
   Web of Science ®Google Scholar
• S.VermaS.L.JainThiourea dioxide catalyzed multi-component coupling reaction for the one step synthesis of naphthopyran derivativesTetrahedron Lett.53201260556058
   Web of Science ®Google Scholar
• S.VermaR.SinghD.TripathiP.GuptaG.M.BahugunaS.L.JainThiourea dioxide with TBHP: a fruitful and greener recipe for the catalytic oxidation of alcoholsRSC Adv.3201341844188
   Web of Science ®Google Scholar
• M.GhashangS.S.MansoorK.AswinThiourea dioxide: an efficient and reusable organocatalyst for the rapid one-pot synthesis of pyrano[4,3-b]pyran derivatives in waterChin. J. Catal.352014127133
   Web of Science ®Google Scholar
• O. Ohura, O. Fujimoto, US Patent 4,233,238 (1980).
   Google Scholar
• S.S.MansoorK.AswinK.LogaiyaS.P.N.SudhanS.MalikAqueous media preparation of 2-amino-4,6-diphenylnicotinonitrile using cellulose sulfuric acidRes. Chem. Intermed.402014871885
   Web of Science ®Google Scholar
• S.S.MansoorK.AswinK.LogaiyaS.P.N.SudhanH.RamadossMelamine trisulfonic acid: a new, efficient and reusable catalyst for the synthesis of some fused pyranopyrrole derivativesJ. Saudi Chem. Soc.201210.1016/j.jscs.2012.12.009
   Web of Science ®Google Scholar
• K.AswinK.LogaiyaS.P.N.SudhanS.S.MansoorAn efficient one-pot synthesis of 1,4-dihydropyridine derivatives through Hantzsch reaction catalysed by melamine trisulfonic acidJ. Taibah Univ. Sci.6201219
   Google Scholar
• S.S.MansoorK.AswinK.LogaiyaS.P.N.SudhanAqua mediated synthesis of acridinediones using reusable silica supported sulfuric acid (SSA) as an efficient catalystJ. Taibah Univ. Sci.201410.1016/j.jtusci.2014.03.003
   Google Scholar
• J.L.WangD.LiuZ.J.ZhangS.ShanX.HanS.M.SrinivasulaC.M.CroceE.S.AlnemriZ.HuangStructure-based discovery of an organic compound that binds Bcl-2 protein and induces apoptosis of tumor cellsProc. Natl. Acad. Sci. U. S. A.97200071247129
   PubMed Web of Science ®Google Scholar
• N.R.KamdarD.D.HaveliwalaP.T.MistryS.K.PatelDesign, synthesis and in vitro evaluation of antitubercular and antimicrobial activity of some novel pyranopyrimidinesEur. J. Med. Chem.45201050565063
   PubMed Web of Science ®Google Scholar
• A.G.MartinezL.J.MarcoFriedlander reaction on 2-amino-3-cyano-4H-pyrans: synthesis of derivatives of 4H-pyran[2,3-b]quinoline, new tacrine analoguesBioorg. Med. Chem. Lett.7199731653170
   Web of Science ®Google Scholar
• H.ValizadehaA.A.AzimiZnO/MgO containing ZnO nanoparticles as a highly effective heterogeneous base catalyst for the synthesis of 4H-pyrans and coumarins in [bmim]BF4J. Iran. Chem. Soc.82011123130
   Web of Science ®Google Scholar
• J.Safaei-GhomiR.TeymuriH.Shahbazi-AlaviA.ZiaratiSnCl2/nano SiO2: a green and reusable heterogeneous catalyst for the synthesis of polyfunctionalized 4H-pyransChin. Chem. Lett.242013921925
   Web of Science ®Google Scholar
• D.KumarV.B.ReddyS.SharadU.DubeS.KapurA facile one-pot green synthesis and antibacterial activity of 2-amino-4H-pyrans and 2-amino-5-oxo-5,6,7,8-tetrahydro-4H-chromenesEur. J. Med. Chem.44200938053809
   PubMed Web of Science ®Google Scholar
• T.-S.JinA.-Q.WangF.ShiL.-S.HanL.-B.LiuT.-S.LiHexadecyldimethyl benzyl ammonium bromide: an efficient catalyst for a clean one-pot synthesis of tetrahydrobenzopyran derivatives in waterARKIVOC1420067886
   Web of Science ®Google Scholar
• H.KiyaniF.GhorbaniPotassium phthalimide promoted green multicomponent tandem synthesis of 2-amino-4H-chromenes and 6-amino-4H-pyran-3-carboxylatesJ. Saudi Chem. Soc.201410.1016/j.jscs.2014.02.004
   Web of Science ®Google Scholar
• S.BanerjeeA.HornH.KhatriG.SeredaA green one-pot multicomponent synthesis of 4H-pyrans and polysubstituted aniline derivatives of biological, pharmacological, and optical applications using silica nanoparticles as reusable catalystTetrahedron Lett.52201118781881
   Web of Science ®Google Scholar
• K.NiknamN.BorazjaniR.RashidianA.JamaliSilica-bonded N-propylpiperazine sodium n-propionate as recyclable catalyst for synthesis of 4H-pyran derivativesChin. J. Catal.34201322452254
   Web of Science ®Google Scholar