Synthesis, Inhaltsverzeichnis Synthesis 2021; 53(04): 775-784DOI: 10.1055/s-0040-1707371 paper From Furan–Yne Systems to para-Benzoquinone Derivatives: Gold-Catalyzed Cyclization and Oxidation, and Further Reduction by Sodium Dithionate Authors Institutsangaben Saman Ahmadi Mohammad Ghanbari∗ Department of Organic Chemistry, Faculty of Chemistry, University of Kashan, Kashan, Iran eMail: ghanbari-m@kashanu.ac.ir Artikel empfehlen Abstract Artikel einzeln kaufen(opens in new window) Alle Artikel dieser Rubrik(opens in new window) Abstract A series of furan–yne systems were transformed into the corresponding para-benzoquinone derivatives by gold(ΙΙΙ) catalyst. The two-step procedure consisted of a phenol synthesis and subsequent oxidation with iodobenzene diacetate. The reactions can be carried out in a one-pot procedure with the same precatalyst. The para-benzoquinone could simply be converted into the corresponding hydroquinones by reduction with sodium dithionate. This protocol features high efficiency, mild conditions, and wide substrate scopes. Key words Key wordsgold catalyst - furfural - alkyne - benzoquinone - one-pot reaction Volltext Referenzen References 1a Thomson RH. Naturally Occurring Quinones IV, Recent Advances. Blackie; London: 1997 1b Thomson RH. Naturally Occurring Quinones III, Recent Advances. Chapman and Hall; London: 1988 2 Biochemistry of Quinones . Green J, McHale D, Morton R. Academic Press; New York: 1965. 261 3 Rao K, Cullen W. In Antibiotics Annual . Welch H, Marti-Ibaiiez F. Wiley-Interscience; New York: 1960 4 Shrestha JP, Subedi YP, Chen L, Chang C.-WT. MedChemComm 2015; 6: 2012 5 Tansuwan S, Pornpakakul S, Roengsumran S, Petsom A, Muangsin N, Sihanonta P, Chaichit N. J. Nat. Prod. 2007; 70: 1620 6a Hartley JA, Reszka K, Lown JW. Photochem. Photobiol. 1988; 48: 19 6b Koyama J. Drug Discov. 2006; 1: 113 7 Dowd P, Zheng ZB. Proc. Natl. Acad. Sci. U. S. A. 1995; 92: 8171 8 Lin AJ, Lillis BJ, Sartorelli AC. J. Med. Chem. 1975; 18: 917 9a Gorin DJ, Sherry BD, Toste FD. Chem. Rev. 2008; 108: 3351 9b Hashmi AS. K. Angew. Chem. 2010; 49: 5232 10a Zeng Z, Jin H, Song X, Wang Q, Rudolph M, Rominger F, Hashmi AS. K. Chem. Commun. 2017; 53: 4304 10b Tokimizu Y, Wieteck M, Rudolph M, Oishi S, Fujii N, Hashmi AS. K, Ohno H. Org. Lett. 2015; 17: 604 10c Jin H, Tian B, Song X, Xie J, Rudolph M, Rominger F, Hashmi AS. K. Angew. Chem. Int. Ed. 2016; 55: 12688 10d Bucher J, Wurm T, Taschinski S, Sachs E, Ascough D, Rudolph M, Rominger F, Hashmi AS. K. Adv. Synth. Catal. 2017; 359: 225 10e Zeiler A, Ziegler MJ, Rudolph M, Rominger F, Hashmi AS. K. Adv. Synth. Catal. 2015; 357: 1507 10f Tšupova S, Hansmann MM, Rudolph M, Rominger F, Hashmi AS. K. Chem. Eur. J. 2017; 23: 5716 10g Miles DH, Toste FD. Enantioselective Gold-Catalyzed Synthesis of Heterocyclic Compounds. In Au-Catalyzed Synthesis and Functionalization of Heterocycles. Bandini M. Springer; Berlin: 2015: 227-248 10h Wei Y, Shi M. ACS Catal. 2016; 6: 2515 11 Pflaesterer D, Hashmi AS. K. Chem. Soc. Rev. 2016; 45: 1331 12 Trost BM. Angew. Chem. Int. Ed. 1995; 34: 259 13 Hashmi AS. K, Frost TM, Bats J. J. Am. Chem. Soc. 2000; 122: 11553 14 Hashmi AS. K, Ghanbari M, Rudolph M, Rominger F. Chem. Eur. J. 2012; 18: 8113 15 Zi W, Toste FD. Chem. Soc. Rev. 2016; 45: 4567 16a Ghanbari M, Jadidi K, Mehrdad M, Assempour N. Tetrahedron 2016; 72: 4355 16b Ghanbari M, Kianmehr E, Behzad SK, Ng SW. J. Iran. Chem. Soc. 2016; 13: 7 16c Kianmehr E, Ghanbari M. Eur. J. Org. Chem. 2012; 256 16d Ghanbari M, Dastjerdi NM, Ahmadi S, Moradi S. J. Iran. Chem. Soc. 2018; 15: 1119 16e Ghanbari M, Moradi S, Setoodehkhah M. Green Chem. Lett. Rev. 2018; 11: 111 16f Kianmehr E, Ghanbari M, Faghih N, Rominger F. Tetrahedron Lett. 2012; 53: 1900 16g Kianmehr E, Ghanbari M, Niri MN, Faramarzi R. J. Comb. Chem. 2010; 12: 41 17 Qiu D, Zheng Z, Mo F, Xiao Q, Tian Y, Zhang Y, Wang J. Org. Lett. 2011; 13: 4988 18 Morey J, Saá JM. Tetrahedron 1993; 49: 105 19a Zope BN, Hibbitts DD, Neurock M, Davis RJ. Science 2010; 330: 74 19b Miyamura H, Matsubara R, Miyazaki Y, Kobayashi S. Angew. Chem. Int. Ed. 2007; 46: 4151 19c Guan B, Xing D, Cai G, Wan X, Yu N, Fang Z, Yang L, Shi Z. J. Am. Chem. Soc. 2005; 127: 18004 19d Piancatelli G, Leonelli F. Org. Synth. 2003; 83: 18 20 Carrettin S, Blanco MC, Corma A, Hashmi AS. K. Adv. Synth. Catal. 2006; 348: 1283 21 Chen YJ, Cui Z, Feng CG, Lin GQ. Adv. Synth. Catal. 2015; 357: 2815 22 Liu G, Cogan DA, Ellman JA. J. Am. Chem. Soc. 1997; 119: 9913 23a Hashmi AS. K, Hengst T, Lothschütz C, Rominger F. Adv. Synth. Catal. 2010; 352: 1315 23b Martín-Matute B, Cárdenas DJ, Echavarren AM. Angew. Chem. Int. Ed. 2001; 40: 4754 Zusatzmaterial Zusatzmaterial Supporting Information (PDF)
