Abstract
A simple and efficient synthesis of N-cyclohexyl-benzofuran derivatives was achieved via a one-pot three-component reaction of cyclohexylisocyanide, an aromatic aldehydes, and phenols in DMF for 10 h with good yields.
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Dean FM (1982) Recent Advances in Furan Chemistry. Part I. Adv Hetero Chem 30: 167–238. doi:10.1016/S0065-2725(08)60028-8
Lipshutz BH (1986) Oxazoles in carboxylate protection and activation. Chem Rev 86: 795–822. doi:10.1021/cr.00075a005
Nakanishi K (1974) Natural products chemistry. Kodansha, Tokyo
Schulte G, Scheuer PJ, McConnel OJ (1980) Two furanosesquiterpene marine metabolites with antifeedant properties. Helv Chim Acta 63: 2159–2163. doi:10.1002/hlca.19800630805
Strenbach DD, Rossana DM (1982) Intramolecular diels-alder reactions of the furan diene: substituent and solvent effects. Tetrahedron Lett 23: 303–306. doi:10.1016/S0040-4039(00)86815-X
Zhu J, Bienayme H (2005) Multicomponent reactions. Wiely-VCH, Weinheim
Litvinov VP (2003) Multicomponent cascade heterocyclisation as a promising route to targeted synthesis of polyfunctional pyridines. Russ Chem Rev 72: 69–85. doi:10.1039/rc030069
Ugi I, Domling A, Horl W (1994) Multicomponent reactions in organic chemistry. Endeavour 18: 115–122. doi:10.1016/S0160-9327(05)80086-9
Tietze LF, Modi A (2000) Multicomponent domino reactions for the synthesis of biologically active natural products and drugs. Med Res Rev 20: 304–322. doi:10.1002/1098-1128(200007)
Ugi I, Domling A, Werner B (2000) Since 1995 the new chemistry of multicomponent reactions and their libraries, including their heterocyclic chemistry. J Heterocycl Chem 37: 647–670. doi:10.1111/1475-4983.00314
Passerini M (1992) Natural product synthesis using multicomponent reaction strategies. Gazz Chim Ital 52: 432–435
Cristau P, Vors JP, Zhu J (2006) Rapid synthesis of cyclopeptide alkaloid-like para-cyclophanes by combined use of Ugi-4CR and intramolecular S N Ar reaction. J QSAR Comb Sci 25: 519–526. doi:10.1002/qsar.200540214
Ugi I, Meyr R, Fetzer U, Steinbruckner C (1959) Versuche mit Isonitrilen. Angew Chem 71: 386–388. doi:10.1002/ange.19590711110
Ugi I, Steinbruckner C (1960) Über ein neues Kondensations-Prinzip. Angew Chem 72: 267–268. doi:10.1002/ange.19600720709
Murakami M (2003) New catalyzed three-component cycloadditions for the synthesis of eight-membered carbocycles. Angew Chem Int Ed 42: 718–720. doi:10.1002/anie.200390200
Bienayme H, Hulme C, Oddon G, Schmitt P (2000) Maximizing synthetic efficiency: multi-component transformations lead the way. Chem Eur J 6: 3321–3329. doi:10.1002/1521-3765(20000915)
Domling A (2002) Recent advances in isocyanide-based multicomponent chemistry. Curr Opin Chem Biol 6: 306–313. doi:10.1016/S1367-5931(02)00328-9
Hulme C, Gore V (2003) Multi-component reactions : emerging chemistry in drug discovery ‘From Xylocain to Crixivan’. Curr Med Chem 10: 51–80. doi:10.2174/0929867033368600
Orru RVA, De Greef M (2003) Recent advances in solution-phase multicomponent methodology for the synthesis of heterocyclic compounds. Synthesis:1471–1499. doi:10.1055/s-2003-40507
Balme G, Bossharth E, Monteiro N (2003) Pd-assisted multicomponent synthesis of heterocycles. Eur J Org Chem 21: 4101–4111. doi:10.1002/ejoc.200300378
Wangelin AJ, Neumann H, Gordes D, Klaus S, Strubing D, Beller M (2003) Multicomponent coupling reactions for organic synthesis: chemoselective reactions with amide-aldehyde mixtures. Chem Eur J 9: 4286–4294. doi:10.1002/chem.200305048
Domling A, Ugi I (2000) Multicomponent reactions with isocyanides. Angew Chem Int Ed 39: 3168–3210. doi:10.1002/1521-3773(20000915)
Marcaccini S, Torroba T (1993) The use of isocyanides in heterocyclic synthesis. A review. Org Prep Proced Int 25: 141–143
Ugi I, Lohberger S, Karl R (1991) In: Trost BM, Fleming I (eds) Comprehensive organic synthesis, vol 2. Pergamon, New York, pp 1083–1086
Heravi MM, Baghernejad B, Oskooie HA, Hekmatshoar R (2008) A novel and facile synthesis of 2-(cyclohexylamino)-6,7-dihydro-3-aryl-1Hindole-4(5H)-ones via a one-pot multi-component reaction. Tetrahedron Lett 49: 6101–6103. doi:10.1016/j.tetlet.2008.08.012
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Baghernejad, B., Heravi, M.M., Oskooie, H.A. et al. A novel and facile synthesis of N-cyclohexyl-benzofurans by one-pot three-component reaction. Mol Divers 15, 245–248 (2011). https://doi.org/10.1007/s11030-010-9228-7
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DOI: https://doi.org/10.1007/s11030-010-9228-7