Abstract
A new approach for the preparation of new 9-(alkyl or aryl)acenaphtho[1,2-b]furan-8-(alky or aryl) amine derivatives has been reported by the catalyst-free one-pot cyclocondensation of (acenaphthylen-1-yloxy)trimethylsilane, alkyl and aryl aldehydes, and aryl and alky isocyanides in refluxing DMF.
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References
Dean FM (1982) Recent advances in furan chemistry. Part I. Adv Heterocycl Chem 30: 167–238. doi:10.1016/S0065-2725(08)60400-6
Lipshutz BH (1986) Oxazoles in carboxylate protection and activation. Chem Rev 86: 795–822. doi:10.1021/cr00075a008
Teimouri MB, Mansouri F (2008) Simple synthesis of 7H-phenaleno[1,2-b]furan-7-one derivatives by one-pot, three-component reactions. J Comb Chem 10: 507–510. doi:10.1021/cc8000103
Sternbach 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
Baghernejad B, Heravi MM, Oskooie HA, Poormohammad N, Khorshidi M, Beheshtiha YS (2011) A novel and facile synthesis of N-cyclohexyl-benzofurans by one-pot three-component reaction. Mol Divers 15: 245–248. doi:10.1007/s11030-010-9228-7
Trost BM (1991) The atom economy—a search for synthetic efficiency. Science 254: 1471–1477. doi:10.1126/science.1962206
Bienaymé 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)
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
Von Wangelin AJ, Neumann H, Gördes D, Klaus S, Strübing 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
Kobayashi S (1999) New methodologies for the synthesis of compound libraries. Chem Soc Rev 28: 1–15. doi:10.1039/A707429H
Tejedor D, González-Cruz D, Santos-Expósito A, Marrero- Tellado JJ, de Armas P, García-Tellado F (2005) Multicomponent domino processes based on the organocatalytic generation of conjugated acetylides: efficient synthetic manifolds for diversity-ori- ented molecular construction. Chem-Eur J 11: 3502–3510. doi:10.1002/chem.200401267
Zhu J (2003) Recent developments in the isonitrile-based multicomponent synthesis of heterocycles. Eur J Org Chem 1133–1144. doi:10.1002/ejoc.200390167
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, Dömling A, Hörl W (1994) Multicomponent reactions in organic chemistry. Endeavour 18: 115–122. doi:10.1016/S0160-9327(05)80086-9
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: 647–658. doi:10.1111/1475-4983.00314
Passerini M (1922) Natural product synthesis using multicomponent reaction strategies. Gazz Chim Ital 52: 432–435
Ugi I, Steinbrückner C (1960) Über ein neues Kondensations-Prinzip. Angew Chem 72: 267–268. doi:10.1002/ange.19600720709
Ugi I., Meyr R., Fetzer U., Steinbrückner C (1959) Versuche mit Isonitrilen Angew Chem 71: 386–388. doi:10.1002/ange.19590711110
Ugi I, Lohberger S, Karl R (1991) The Passerini and Ugi reactions. Compr Org Synth 2: 1083–1109. doi:10.1016/B978-0-08-052349-1.00057-3
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
Marcaccini S, Torroba T (1993) The use of isocyanides in heterocyclic synthesis. Org Prep Proced Int 25: 141–208. doi:10.1080/00304949309457947
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
Dömling A, Ugi I (2000) Multicomponent reactions with isocyanides. Angew Chem Int Ed 39: 3169–3210. doi:10.1002/1521-3773(20000915)
Dömling A (2002) Recent advances in isocyanide-based multicomponent chemistry. Curr Opin Chem Biol 6: 306–313. doi:10.1016/S1367-5931(02)00328-9
Cristau P, Vors JP, Zhu J (2006) Rapid synthesis of cyclopeptide alkaloid-like para-cyclophanes by combined use of Ugi-4CR and intramolecular SNAr reaction. QSAR Comb Sci 25: 519–526. doi:10.1002/qsar.200540214
Balme G, Bossharth E, Monteiro N (2003) Pd-assisted multicomponent synthesis of heterocycles. Eur J Org Chem 4101–4111. doi:10.1002/ejoc.200300378
Nair V, Menon RS, Vinod AU, Viji S (2002) A facile three-component reaction involving [4+1] cycloaddition leading to furan annulated heterocycles. Tetrahedron Lett 43: 2293–2295. doi:10.1016/S0040-4039(02)00226-5
Shaabani A, Teimouri MB, Bijanzadeh HR (2002) One-pot three component condensation reaction in water: An efficient and improved procedure for the synthesis of furo[2,3-d]pyrimidine-2,4(1H,3H)-diones. Tetrahedron Lett 43: 9151–9154. doi:10.1016/S0040-4039(02)02260-8
Shaabani A, Teimouri MB, Bijanzadeh HR (2004) A novel three-component tetrahydrobenzofuran synthesis. Monatsh Chem 135: 441–446. doi:10.1002/chin.200435097
Shaabani A, Teimouri MB, Bijanzadeh HR (2004) One-pot three-component condensation reactions in water. An efficient and improved procedure for the synthesis of furan annulated heterocycles. Monatsh Chem 135: 589–593. doi:10.1007/s00706-003-0126-x
Shaabani A, Teimouri MB, Samadi S, Soleimani K (2005) Microwave-assisted three-component condensation on montmorillonite K10: Solvent-free synthesis of furopyrimidines, furocoumarins, and furopyranones. Synth Commun 35: 535–541. doi:10.1002/chin.200531116
Teimouri MB, Bazhrang R (2006) Shaken not stirred: a facile synthesis of 1,4-bis(furo[2,3-d]-pyrimidine-2,4(1H,3H)-dione-5-yl) benzenes by one-pot reaction of isocyanides, N,N′-dimethylbarbituric acid, and terephthaldialdehyde. Bioorg Med Chem Lett 16: 3697–3701. doi:10.1016/j.bmcl.2006.04.065
Teimouri MB, Khavasi HR (2007) One-pot three-component regioselective synthesis of linear naphtho[2,3-b]-furan-4,9-diones. Tetrahedron 63: 10269–10275. doi:10.1016/j.tet.2007.07.082
Song JJ, Tan Z, Reeves JT, Fandrick DR, Yee NK, Senanayake CH (2008) N-heterocyclic carbene-catalyzed silyl enol ether for- mation. Org Lett 10: 877–880. doi:10.1021/ol703025b
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Sandaroos, R., Damavandi, S., Salimi, M. et al. New approach for the synthesis of novel acenaphtho[1,2-b]furan-8-amines. Mol Divers 16, 269–277 (2012). https://doi.org/10.1007/s11030-012-9356-3
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DOI: https://doi.org/10.1007/s11030-012-9356-3