Abstract
New methods for the synthesis of spiro compounds containing dihydrofuran and coumarin moieties from 3-bromo-4-hydroxycoumarins as cyclic α-halo compound based on a pyridinium-ylide-assisted three-component tandem reaction is investigated. To the best of our knowledge, employing cyclic α-halo compounds for the synthesis of dihydrofuran-fused coumarin via a pyridinium ylide has not been reported yet.
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Thompson LA (2000) recent applications of polymer-supported reagents and scavengers in combinatorial, parallel, or multistep synthesis. Curr Opin Chem Biol 4: 324–337. doi:10.1016/S1367-5931(00)00096-X
Nefzi A, Ostresh JM, Houghten RA (1997) the Current Status of Heterocyclic Combinatorial Libraries. Chem Rev 97: 449–472. doi:10.1021/cr960010b
Padwa A (2003) application of cascade processes toward heterocyclic synthesis. Pure Appl Chem 75: 47–62. doi:10.1351/pac200375010047
Nicolaou K.C, Edmonds DJ, Bulger PG (2006) Cascade Reactions in Total Synthesis. Angew Chem Int Ed 45: 7134–7186. doi:10.1002/anie.200601872
O’Kennedy R, Thornes RD (1997) Coumarins: biology, applications and mode of action. Wiley, Chichester
Murray RDH, Mendez J, Brown SA (1982) The natural coumarins: occurrence, chemistry and biochemistry. Wiley, New York
Tsai FT, Singh OM, Skarzynski T, Wonacott AJ, Weston S, Tucker A, Pauptit RA, Breeze AL, Poyser JP, O’Brien R, Ladbury JE, Wigley DB (1997) The high-resolution crystal structure of a 24-kda gyrase b fragment from e. coli complexed with one of the most potent coumarin inhibitors, clorobiocin. Struct Funct Genet 28: 41–52. doi:10.1002/(SICI)10970134(199705)28:1<41::AID-PROT4>3.0.CO;2-M
Lee S, Sivakumar K, Shin W-S, Xiea F, Wanga Q (2006) Synthesis and anti-angiogenesis activity of coumarin derivatives. Bio Med Chem Lett 16: 4596–4599. doi:10.1016/j.bmcl.2006.06.007
Cravotto G, Nano GM, Palmisanob G, Tagliapietraa S (2001) An asymmetric approach to coumarin anticoagulants via hetero-Diels–Alder cycloaddition. Tetrahedron 12: 707–709. doi:10.1016/S0957-4166(01)00124-0
Kontogiorgis CA, Hadjipavlou-Litina DJ (2005) Synthesis and antiinflammatory activity of coumarin derivatives. J Med Chem 48: 6400–6408. doi:10.1021/jm0580149
Wu J, Liao Y, Yang Z (2001) Synthesis of 4-substituted coumarins via the palladium-catalyzed cross-couplings of 4-tosylcoumarins with terminal acetylenes and organozinc reagents. J Org Chem 66: 3642–3645. doi:10.1021/jo0102157
Kotharkar SA, Shinde DB (2006) Synthesis of antimicrobial 2,9,10-trisubstituted-6-oxo-7,12-dihydro-chromeno[3,4- b]quinoxalines. Bioorg Med Chem Lett 16: 6181–6184. doi:10.1016/j.bmcl.2006.09.040
Finet JP (1998) Ligand Coupling Reactions with Heteroatomic Compounds. Elsevier Science. Ltd., Oxford
Schiedel MS, Briehn CA, Bauerle P (2001) Single-compound libraries of organic materials: parallel synthesis and screening of fluorescent dyes. Angew Chem Int Ed 40: 4677–4680. doi:10.1002/1521-3773(20011217)40:24<4677::AID-ANIE4677>3.0.CO;2-U
Kowalski CJ, Weber AE, Fields KW (1982) Alpha-Keto dianion precursors via conjugate additions to cyclic alpha-bromo enones. J Org Chem 47: 5088–5093. doi:10.1021/jo00147a008
Ley SV, Whittle AJ (1981) a convenient preparation of 2-haloenones from enones using phenylselenium halides. Tetrahedron Lett 22: 3301–3304. doi:10.1016/S0040-4039(01)81890-6
Eicher T, Hauptmann S (2003) The chemistry of heterocycles: structure, reactions, syntheses, and applications. Wiley, Weinheim
Elinson MN, Vereshchagin AN, Stepanov NO, Belyakov PA, Nikishin GI (2010) Cascade assembly of N,N′-dialkylbarbituric acids and aldehydes: a simple and efficient one-pot approach to the substituted 1,5-dihydro-2H,2′ H-spiro(furo[2,3-d]pyrimidine-6,5′-pyrimidine)-2,2′,4,4′,6′(1′H,3H,3′H)-pentone framework. Tetrahedron Lett 51: 6598–6601. doi:10.1016/j.tetlet.2010.10.041
Chuang CP, Tsai AI (2006) Pyridinium Ylides in the Synthesis of 2, 3-Dihydrofurans. Synthesis 675-679 doi:10.1055/s-2006-926300
Doyle MP, Forbes DC, Protopopova MN, Stanley SA, Vasbinder MM, Xavier KR (1997) Stereocontrol in Intermolecular Dirhodium(II)-catalyzed carbonyl ylide formation and reactions. Dioxolanes and dihydrofurans. J Org Chem 62: 7210–7215. doi:10.1021/jo970641l
Anaç O, Güngör FS, Güngör FS, Güngör FS, Cansever MS (2008) Carbonyl ylide reactions of α-benzylidene-β-dicarbonyl compounds: competitive formation of dihydrofurans and dihydrobenzoxepines. Tetrahedron Lett 49: 1062–1065. doi:10.1016/j.tetlet.2007.11.197
Mross G, Holtz E, Langer P (2006) Synthesis of 2-alkenyl-3-(alkoxycarbonyl)furans Based on Feist-Benary Cyclocondensation of (2,4-Dioxobutylidene)phosphoranes with α-Haloketones and α-chloracetaldehyde. J Org Chem 71: 8045–8049. doi:10.1021/jo061153t
Ranu BC, Adak L, Banerjee S (2008) Ionic liquid promoted interrupted Feist–Benary reaction with high diastereoselectivity. Tetrahedron Lett 49: 4613–4617. doi:10.1016/j.tetlet.2008.05.083
Adamo M, Suresh S, Piras L (2009) Reaction of 5-(1-bromo-2-aryl-vinyl)-3-methyl-4-nitro-isoxazoles and 1,3-dicarbonyl compounds. Tetrahedron 65: 5402–5408. doi:10.1016/j.tet.2009.04.058
Chuang CP, Tsai AI (2008) α-Nitro carbonyl compounds in the synthesis of 2,3-dihydrofurans. Tetrahedron 64: 7511–7516. doi:10.1016/j.tet.2008.05.122
Calter MA, Zhu C (2002) Scope and diastereoselectivity of the “interrupted” Feist–Bénary reaction. Org Lett 4: 205–208. doi:10.1021/ol0169978
Calo V, Scordari F, Nacci A, Schingaro E, D’Accolti L, Monopoli A (2003) Stereoselective synthesis of tetrasubstituted 2,3-dihydrofurans by one-step cyclization of β-ketosulfides of benzothiazole and aldehydes in ionic liquids. J Org Chem 68: 4406–4409. doi:10.1021/jo026849a
Arai S, Nakayama K, Suzuki Y, Hatano K, Shioiri T (1998) Stereoselective synthesis of dihydrofurans under phase-transfer catalyzed conditions. Tetrahedron Lett 39: 9739–9742. doi:10.1016/S0040-4039(98)02239-4
Sun XL, Tang Y (2008) Ylide-initiated Michael addition-cyclization reactions beyond cyclopropanes. Acc Chem Res 41: 937–948. doi:10.1021/ar800108z
Redon S, Leleu S, Pannecoucke X, Franck X, Outurquin F (2008) New synthesis and cyclopropanation of α-phenylselanyl α,β-unsaturated ketones with non-stabilized phosphorus ylides. Tetrahedron 64: 9293–9304. doi:10.1016/j.tet.2008.07.025
Moorhoff CM (1996) Novel reactions of arsonium ylides and substituted 2H-pyran-5-carboxylates, a new preparation for functionalised vinylcyclopropanecarboxylates and dihydrofurans. Tetrahedron Lett 37: 9349–9352. doi:10.1016/S0040-4039(97)82961-9
Yang Z, Fan M, Mu R, Liu W, Liang Y (2005) A facile synthesis of highly functionalized dihydrofurans based on 1,4-diazabicyclo[2.2.2]octane (DABCO) catalyzed reaction of halides with enones. Tetrahedron 61: 9140–9146. doi:10.1016/j.tet.2005.07.009
Wang Q-F, Hou H, Hui L, Yan Ch-G (2009) Diastereoselective synthesis of trans-2,3-dihydrofurans with pyridinium ylide assisted tandem reaction. J Org Chem 74: 7403–7406. doi:10.1021/jo901379h
Wang GW, Gao J (2009) Selective formation of spiro dihydrofurans and cyclopropanes through unexpected reaction of aldehydes with 1,3-dicarbonyl compounds. Org Lett 11: 2385–2388. doi:10.1021/ol900451d
Prasanna P, Balamurugan K, Subbu P, Menéndez JC (2011) A facile, three-component domino protocol for the microwave-assisted synthesis of functionalized naphtho[2,3-b]furan-4,9-diones in water. Green Chem 13: 2123–2129. doi:10.1039/C0GC00952K
Cota L, Chimentao R, Sueiras J, Medina F (2008) The DBU-H2O complex as a new catalyst for aldol condensation reactions. Catal Commun 9: 2090–2094. doi:10.1016/j.catcom.2008.03.047
Pihko PM, Laurikainen KM, Usano A, Nyberg AI, Kaavi JA (2006) Effect of additives on the proline-catalyzed ketone–aldehyde aldol reactions. Tetrahedron 62: 317–328. doi:10.1016/j.tet.2005.09.070
Lee MJ, Park DY, Lee KY, Kim JN (2006) Base-catalyzed domino reaction toward 3-benzylidenecyclohexenes: DBU-promoted sequential Michael, aldol, dehydration, and dealkoxycarbonylation. Tetrahedron Lett 47: 1833–1837. doi:10.1016/j.tetlet.2005.12.134
Ghosh N (2004) DBU (1,8-diazabicyclo[5.4.0]undec-7-ene)-A nucleophillic Base. Synlett 574–575. doi:10.1055/s-2004-815436
Pérez ER, Santos RHA, Gambardella MTP, de Macedo LGM, Launay J-C, Franco DW (2004) Activation of carbon dioxide by bicyclic amidine. J Org Chem 69: 8005–8011. doi:10.1021/jo049243q
Dove AP, Pratt RC, Lohmeijer GG, Hedrick JK (2005) Thiourea-based bifunctional organocatalysis: supramolecular recognition for living polymerization. J Am Chem Soc 127: 13798–13799. doi:10.1021/ja0543346
Shieh WC, Dell S, Repic D (2002) Nucleophilic catalysis with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) for the esterification of carboxylic acids with dimethyl carbonate. J Org Chem 67: 2188–2191. doi:10.1021/jo011036s
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Ahadi, S., Abaszadeh, M. & Bazgir, A. Organocatalytic three-component cascade reaction for the synthesis of spiro[indeno[1,2-b]furan]-triones. Mol Divers 16, 299–306 (2012). https://doi.org/10.1007/s11030-012-9363-4
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DOI: https://doi.org/10.1007/s11030-012-9363-4