RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2012; 44(8): 1171-1177
DOI: 10.1055/s-0031-1290588
DOI: 10.1055/s-0031-1290588
special topic
Hypervalent Iodine Mediated Oxidative Cyclization of o-Hydroxystilbenes into Benzo- and Naphthofurans
Weitere Informationen
Publikationsverlauf
Received: 06. Februar 2012
Accepted: 20. Februar 2012
Publikationsdatum:
27. März 2012 (online)
Abstract
A new and convenient metal-free cyclization of ortho-hydroxystilbenes into 2-arylbenzofurans and 2-arylnaphthofurans mediated by hypervalent iodine reagents is described. The cyclization products are isolated in good to excellent yields using stoichiometric (diacetoxyiodo)benzene in acetonitrile.
-
References
- 1a Gommers FJ. Phytochemistry 1971; 10: 1945
- 1b Shibata S, Miura Y, Sugimura H, Tozoizumi Y. J. Pharm. Soc. Jpn. 1948; 68: 300
- 1c Stoll A, Brack A, Renz J. Schweiz. Z. Pathol. Bakteriol. 1950; 13: 729
- 1d Stark JB, Walter ED, Owens HS. J. Am. Chem. Soc. 1950; 72: 1819
- 1e Geissman TA, Heaton CD. J. Am. Chem. Soc. 1943; 65: 677
- 1f Jakupovic J, Schuster A, Ganzer U, Bohlmann F, Boldt PE. Phytochemistry 1990; 29: 2217
- 1g Miles DH, Chittawong V, Lho DS, Payen AM, De la Cruz AA, Gomez ED, Weeks JA, Atwood JL. J. Nat. Prod. 1991; 54: 286
- 1h Goel A, Dixit M. Tetrahedron Lett. 2004; 45: 8819
- 1i Clair JJ. L, Rheingold AL, Burkart MD. J. Nat. Prod. 2011; 74: 2045
- 2a Miles DH, Lho DS, De la Cruz AA, Gomez ED, Weeks JA, Atwood JL. J. Org. Chem. 1987; 52: 2930
- 2b Irie H, Matsumoto R, Nishimura M, Zhang Y. Chem. Pharm. Bull. 1990; 38: 1852
- 2c Zubaidha PK, Chavan SP, Racherla US, Ayyangar NR. Tetrahedron 1991; 47: 5759
- 3a Bohlmann F, Zdero C. Chem. Ber. 1977; 110: 487
- 3b Braga de Oliveira A, De Oliveira GG, Carazza F, Braz Filho R, Moreira Bacha CT, Bauer L, de A B Silva GA, Siqueira NC. S. Tetrahedron Lett. 1978; 19: 2653
- 4 Ohemeng KA, Apollina MA, Nguyen VN, Schwender CF, Singer M, Steber M, Ansell J, Argentieri D, Hageman W. J. Med. Chem. 1994; 37: 3663
- 5 Kiyama R, Homna T, Hayashi K, Ogawa M, Hara M, Fujimoto M, Fujishita T. J. Med. Chem. 1995; 38: 2728
- 6 Kozikowsky AP, Ma D, Du L, Lewin NE, Blumberg PM. J. Am. Chem. Soc. 1995; 117: 6666
- 7 Aslam SN, Stevenson PC, Phythian SJ, Vietch NC, Hall DR. Tetrahedron 2006; 62: 4214
- 8 Einhorn J, Demerseman P, Royer R, Cavier R, Gayral P. Eur. J. Med. Chem. 1984; 19: 405
- 9 Khan MW, Alam MJ, Rashid MA, Chowdhury R. Bioorg. Med. Chem. 2005; 13: 4796
- 10 Zhou X, Li M, Wang XB, Wang T, Kong LY. Molecules 2010; 15: 8593
- 11a Li C, Zhang Y, Li P, Wang L. J. Org. Chem. 2011; 76: 4692
- 11b Zhou L, Shi Y, Xiao Q, Liu Y, Ye F, Zhang Y, Wang J. Org. Lett. 2011; 13: 968
- 11c Guo X, Yu R, Li H, Li Z. J. Am. Chem. Soc. 2009; 131: 17387
- 11d Farago J, Kotschy A. Synthesis 2009; 85
- 11e Ferreira EM, Zhang H, Stoltz BM. Tetrahedron 2008; 64: 5987
- 11f Eidamshaus C, Burch JD. Org. Lett. 2008; 10: 4211
- 11g Csekei M, Novak Z, Kotschy A. Tetrahedron 2008; 64: 8992
- 11h Tadd AC, Fielding MR, Willis MC. Tetrahedron Lett. 2007; 48: 7578
- 11i Lu B, Wang B, Zhang Y, Ma D. J. Org. Chem. 2007; 72: 5337
- 11j Anderson KW, Ikawa T, Tundel RE, Buchwald SL. J. Am. Chem. Soc. 2006; 128: 10694
- 11k Fürstner A, Davies PW. J. Am. Chem. Soc. 2005; 127: 15024
- 11l Nakamura I, Mizushima Y, Yamamoto Y. J. Am. Chem. Soc. 2005; 127: 15022
- 11m Yue D, Yao T, Larock RC. J. Org. Chem. 2005; 70: 10292
- 11n Zhang H, Ferreira EM, Stoltz BM. Angew. Chem. Int. Ed. 2004; 43: 6144
- 11o Chen C, Lieberman DR, Larsen RD, Verhoeven TR, Reider PJ. J. Org. Chem. 1997; 62: 2676
- 11p Zhao B, Lu X. Org. Lett. 2006; 8: 5987
- 12 Takeda N, Miyata O, Naito T. Eur. J. Org. Chem. 2007; 1491
- 13 Huang XC, Liu YL, Liang Y, Pi SF, Wang F, Li JH. Org. Lett. 2008; 10: 1525
- 14 Pan C, Yu J, Zhou Y, Wang Z, Zhou MM. Synlett 2006; 1657
- 15 Ghosh S, Das J. Tetrahedron Lett. 2011; 52: 1112
- 16a Wirth T. Angew. Chem. Int. Ed. 2001; 40: 2812
- 16b Wirth T In Organic Synthesis Highlights V . Schmalz H.-G, Wirth T. Wiley-VCH; Weinheim: 2003: 144
- 16c Hypervalent Iodine Chemistry: Modern Developments in Organic Synthesis. In Topics in Current Chemistry. Vol. 224. Wirth T. Springer; Berlin: 2003
- 16d Wirth T. Angew. Chem. Int. Ed. 2005; 44: 3656
- 16e Moriarty RM. J. Org. Chem. 2005; 70: 2893
- 16f Richardson RD, Wirth T. Angew. Chem. Int. Ed. 2006; 45: 4402
- 16g Ladziata U, Zhdankin VV. Synlett 2007; 527
- 16h Zhdankin VV, Stang PJ. Chem. Rev. 2008; 108: 5299
- 16i Merritt EA, Olofsson B. Angew. Chem. Int. Ed. 2009; 48: 9052
- 16j Pouységu L, Deffieux D, Quideau S. Tetrahedron 2010; 66: 2235
- 16k Zhdankin VV. J. Org. Chem. 2011; 76: 1185
- 16l Uyanik M, Ishihara K. ChemCatChem 2012; 4: 177
- 17a Boye AC, Meyer D, Ingison CK, French AN, Wirth T. Org. Lett. 2003; 5: 2157
- 17b Farooq U, Schäfer S, Shah AA, Freudendahl DM, Wirth T. Synthesis 2010; 1023
- 17c Farid U, Wirth T. Angew. Chem. Int. Ed. 2012; 51 DOI: 10.1002/anie.201107703
- 18 Singh FV, Wirth T. Org. Lett. 2011; 13: 6504
- 19 Schäfer S, Wirth T. Angew. Chem. Int. Ed. 2010; 49: 2786
- 20 Huang SH, Chen JR, Tsai FY. Molecules 2010; 15: 315
- 21 Mylona A, Nikokavouras J, Takakis IM. J. Chem. Res., Synop. 1986; 12: 433
- 22 Lion CJ, Matthews CS, Stevens MF. G, Westwell AD. J. Med. Chem. 2005; 48: 1292
- 23 Jaseer EA, Prasad DJ. C, Sekar G. Tetrahedron 2010; 66: 2077
- 24 Astoin J, Demerseman P, Riveron A, Royer R. J. Heterocycl. Chem. 1977; 14: 867
- 25 Carril M, SanMartin R, Tellitu I, Domínguez E. Org. Lett. 2006; 8: 1467
- 26 Isono N, Lautens M. Org. Lett. 2009; 11: 1329
- 27 Takeda N, Miyata O, Naito T. Eur. J. Org. Chem. 2007; 1491
- 28 Jacubert M, Provot O, Peyrat J.-F, Hamze A, Brion J.-D, Alami M. Tetrahedron 2010; 66: 3775
- 29 Carril M, Correa A, Bolm C. Angew. Chem. Int. Ed. 2008; 47: 4862
- 30 Denmark SE, Smith RC, Chang WT, Muhuhi JM. J. Am. Chem. Soc. 2009; 131: 3104
- 31 Seggio A, Priem G, Chevallier F, Mongin F. Synthesis 2009; 3617
- 32 Jana R, Paul S, Biswas A, Ray JK. Tetrahedron Lett. 2010; 51: 273