Abstract
A silver(I)-catalyzed cascade heterocyclization of 2-(1-alkynyl)-2-alken-1-ones with aryl-amines is described to synthesize trisubstituted furans in moderate to good yields. Tertiary amine is also efficient in this reaction. This transformation proceeds smoothly with the formation of C–N or C–C bonds in one-pot with good functional group tolerance under mild conditions.
Graphical Abstract
Similar content being viewed by others
References
Blanc A, Bénéteau V, Weibel J-M, Pale P (2016) Silver & gold-catalyzed routes to furans and benzofurans. Org Biomol Chem 14:9184–9205. doi:10.1039/c6ob01468b
CCDC 1019024 (2017) (3fa) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via http://www.ccdc.cam.ac.uk/data_request/cif
Chen WL, Li J, Zhu YH, Ye LT, Hu W, Mo WM (2011) AgOTf-catalyzed cyclization of enynals or enynones with amines: an efficient synthesis of 1,2,4-trisubstituted pyrroles and 2,3,5-trisubstituted Furans. ARKIVOC 9:381–392
Cornil J, Gonnard L, Bensoussan C, Serra-Muns A, Gnamm C, Commandeur C, Commandeur M, Reymond S, Guérinot A, Cossy J (2015) Iron- and indium-catalyzed reactions toward nitrogen- and oxygen-containing saturated heterocycles. Acc Chem Res 48:761–773. doi:10.1021/ar5004412
Gao HY, Zhang JL (2012) Cationic rhodium(I)-catalyzed regioselective tandem heterocyclization/[3+2] cycloaddition of 2-(1-alkynyl)-2-alken-1-ones with alkynes. Chem Eur J 18:2777–2782. doi:10.1002/chem.201103924
Gao HY, Wu XX, Zhang JL (2010a) Exo/endo selectivity-control in Lewis-acid catalyzed tandem heterocyclization/formal [4+3] cycloaddition: synthesis of polyheterocycles from 2-(1-alkynyl)-2-alken-1-ones and 1,3-diphenylisobenzofuran. Chem Commun 46:8764–8766. doi:10.1039/C0CC02778B
Gao HY, Zhao XL, Yu YH, Zhang JL (2010b) Highly substituted furo[3,4-c]azepines by gold(I)-catalyzed diastereoselective tandem double heterocyclizations and 1,2-alkyl migration. Chem Eur J 16:456–459. doi:10.1002/chem.200901813
Gao HY, Wu XX, Zhang JL (2011) Gold(I)-catalyzed, highly diastereoselective, tandem heterocyclizations/[3+2] cycloadditions: synthesis of highly substituted cyclopenta[c]furans. Chem Eur J 17:2838–2841. doi:10.1002/chem.201003363
Ghosh J, Biswas P, Sarkar T, Drew MGB, Bandyopadhyay C (2016) 5-Aryl-2-(2-hydroxyphenyl)furan-3-carbaldehyde: synthesis and study on its ring-chain tautomerism. Tetrahedron Lett 57:3354–3357. doi:10.1016/j.tetlet.2016.06.069
Gulevich AV, Dudnik AS, Chernyak N, Gevorgyan V (2013) Transition metal-mediated synthesis of monocyclic aromatic heterocycles. Chem Rev 113:3084–3213. doi:10.1021/cr300333u
Harmata M (2010) Silver-catalyzed cycloisomerization reactions. In: Belmont P (ed) Silver in organic chemistry, vol 5. John Wiley & Sons Inc, Hoboken, pp 143–162
He T, Gao P, Zhao SC, Shi YD, Liu XY, Liang YM (2013a) Platinum(IV)-catalyzed regioselective synthesis of highly substituted 4H-cyclopenta[b]furans via cascade hetero-cyclization of 2-(1-alkynyl)-3-aryl-2-propenals with arylethenes. Adv Synth Catal 355:365–369. doi:10.1002/adsc.201200597
He T, Gao P, Qiu YF, Yan XB, Liu XY, Liang YM (2013b) Gold-catalyzed intermolecular reaction of 2-(1-alkynyl)-2-alken-1-ones with diarylethenes to construct polysubstituted cyclopenta[c]furans through a cascade heterocyclization/[3+2] cycloaddition sequence. RSC Adv 3:19913–19916. doi:10.1039/C3RA44467H
Hu F, Shao XX, Zhu DH, Lu L, Shen QL (2014) Silver-catalyzed decarboxylative trifluoromethylthiolation of aliphatic carboxylic acids in aqueous emulsion. Angew Chem Int Ed 53:6105–6109. doi:10.1002/anie.201402573
Hu Z, Dong J, Men Y, Lin Z, Cai J, Xu X (2017) Silver-catalyzed chemoselective [4+2] annulation of two isocyanides: a general route to pyridone-fused carbo- and heterocycles. Angew Chem Int Ed 56:1805–1809. doi:10.1002/anie.201611024
Ji KG, Shu XZ, Zhao SC, Zhu HT, Niu YN, Liu XY, Liang YM (2009) Novel carbon–carbon bond formation from propargylic alcohols and olefin toward five-membered heterocyclic rings catalyzed by AgSbF6. Org Lett 11:3206–3209. doi:10.1021/ol901270b
Keay BA, Dibble PW (1996) Furans and their Benzo derivatives: applications. In: Katritzky AR, Donnelly C, Rees W, Scriven EFV (eds) Comprehensive heterocyclic chemistry II, vol 2. Pergamon Press, Oxford, pp 395–436
Lee HK, Chan KF, Hui CW, Yim HK, Wu XW, Wong HNC (2005) Use of furans in synthesis of bioactive compounds. Pure Appl Chem 77:139–143
Li WB, Zhang JL (2010) Tetrasubstituted furans by PdII/CuI-cocatalyzed three-component domino reactions of 2-(1-alkynyl)-2-alken-1-ones, nucleophiles and diaryliodonium salts. Chem Commun 46:8839–8841. doi:10.1039/c0cc03450a
Liu RR, Zhang JL (2011) Polyheterocycles by palladium(II)-catalyzed oxidative domino reactions involving direct C–H functionalization. Adv Synth Catal 353:36–40. doi:10.1002/adsc.201000670
Liu F, Yu YH, Zhang JL (2009) Highly substituted furo[3,4-d][1,2]oxazines: gold-catalyzed regiospecific and diastereoselective 1,3-dipolar cycloaddition of 2-(1-alkynyl)-2-alken-1-ones with nitrones. Angew Chem Int Ed 48:5505–5508. doi:10.1002/anie.200901299
Liu F, Qian DY, Li L, Zhao XL, Zhang JL (2010) Diastereo- and enantioselective gold(I)-catalyzed intermolecular tandem cyclization/[3+3]cycloadditions of 2-(1-alkynyl)-2-alken-1-ones with nitrones. Angew Chem Int Ed 49:6669–6672. doi:10.1002/anie.201003136
Liu JQ, Liu ZH, Liao PQ, Zhang L, Tu T, Bi XH (2015) Silver-catalyzed cross-coupling of isocyanides and active methylene compounds by a radical process. Angew Chem Int Ed 54:10618–10622. doi:10.1002/anie.201504254
Meegan DMXMJ (1984) Furans and their Benzo derivatives: (iii) synthesis and applications. In: Katritzky AR, Rees CW (eds) Comprehensive heterocyclic chemistry, vol 4. Pergamon, Oxford, pp 657–712
Nakanishi K (1974) Natural Products Chemistry. Kodansha, Toyko, p 392
Oh CH, Reddy VR, Kim A, Rhim CY (2006) Nucleophile-assisted Pt-catalyzed cyclization of enynones: an access to synthesis of highly substituted furans. Tetrahedron Lett 47:5307–5310. doi:10.1016/j.tetlet.2006.05.119
Patil NT, Yamamoto Y (2008) Coinage metal-assisted synthesis of heterocycles. Chem Rev 108:3395–3442. doi:10.1021/cr050041j
Patil NT, Wu H, Yamamoto Y (2005) Cu(I) catalyst in DMF: an efficient catalytic system for the synthesis of furans from 2-(1-alkynyl)-2-alken-1-ones. J Org Chem 70:4531–4534. doi:10.1021/jo050191u
Rubin M, Sromek AW, Gevorgyan V (2003) New advances in selected transition metal-catalyzed annulations. Synlett 15:2265–2291. doi:10.1055/s-2003-43334
Wang H, Guo LN, Duan XH (2014) Silver-catalyzed decarboxylative acylfluorination of styrenes in aqueous media. Chem Commun 50:7382–7384. doi:10.1039/C4CC02800G
Wang YD, Zhang PC, Qian DY, Zhang JL (2015) Highly regio-, diastereo-, and enantioselective gold(I)-catalyzed intermolecular annulations with N-allenamides at the proximal C=C bond. Angew Chem Int Ed 54:14849–14852. doi:10.1002/anie.201507165
Weibel JM, Blanc A, Pale P (2008) Ag-mediated reactions: coupling and heterocyclization reactions. Chem Rev 108:3149–3173. doi:10.1021/cr078365q
Wong HNC, Yu P, Yick CY (1999) The use of furans in natural product syntheses. Pure Appl Chem 71:1041–1044
Xiao YJ, Zhang JL (2008) Tetrasubstituted furans by a PdII-catalyzed three-component michael addition/cyclization/cross-coupling reaction. Angew Chem Int Ed 47:1903–1906. doi:10.1002/anie.200704531
Xiao YJ, Zhang JL (2009) Palladium(II)-catalyzed domino reaction of 2-(1-alkynyl)-2-alken-1-ones with nucleophiles: scope, mechanism and synthetic application in the synthesis of 3,4-fused bicyclic tetrasubstituted furans. Adv Synth Catal 351:617–629. doi:10.1002/adsc.200800715
Yamamoto Y (2012) Transition-metal-catalyzed cycloisomerizations of α, ω-dienes. Chem Rev 112:4736–4769. doi:10.1021/cr300050n
Yao TL, Zhang XX, Larock RC (2004) AuCl3-catalyzed synthesis of highly substituted furans from 2-(1-alkynyl)-2-alken-1-ones. J Am Chem Soc 126:11164–11165. doi:10.1021/ja0466964
Yao TL, Zhang XX, Larock RC (2005) Synthesis of highly substituted furans by the electrophile-induced coupling of 2-(1-alkynyl)-2-alken-1-ones and nucleophiles. J Org Chem 70:7679–7685. doi:10.1021/jo0510585
Zeni G, Larock RC (2004) Synthesis of heterocycles via palladium π-olefin and π-alkyne chemistry. Chem Rev 104:2285–2310. doi:10.1021/cr020085h
Zhao WX, Zhang JL (2010) Rhodium-catalyzed domino heterocyclization and [(3+2)+2] : construction of fused tricycloheptadienes. Chem Commun 46:7816–7818. doi:10.1039/C0CC02382
Zhou LJ, Zhang MR, Li WB, Zhang JL (2014) Furan-based o-quinodimethanes by gold-catalyzed dehydrogenative heterocyclization of 2-(1-alkynyl)-2-alken-1-ones: a modular entry to 2,3-furan fused carbocycles. Angew Chem Int Ed 53:6542–6545. doi:10.1002/anie.201403709
Acknowledgements
The authors gratefully acknowledge the National Natural Science Foundation of China (NSFC 20967006) and Qinghai Normal University (15RZ12) for financial support.
Author information
Authors and Affiliations
Corresponding authors
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
He, T., Chi, Y. & Chen, Y. Synthesis of trisubstituted furans via Ag-catalyzed cascade heterocyclization of 2-(1-alkynyl)-2-alken-1-ones with aryl-amines. Chem. Pap. 72, 691–696 (2018). https://doi.org/10.1007/s11696-017-0323-4
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11696-017-0323-4