Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2009(4): 674-680
DOI: 10.1055/s-0028-1083339
DOI: 10.1055/s-0028-1083339
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkAn Expedient Synthesis of Bis-Fused Benzofuran and a Two-Directional Ring-Closing Metathesis for the Synthesis of Bisbenzoxepines and Bisbenzoxocines
Further Information
Received
25 September 2008
Publication Date:
27 January 2009 (online)
Publication History
Publication Date:
27 January 2009 (online)

Abstract
Synthesis of bis-fused benzofuran derivatives by the implementation of palladium-mediated intramolecular cyclization is described. To our knowledge, this is the first report of the synthesis of bis-fused benzofuran by this protocol. Bisbenzoxepine and bisbenzoxocine derivatives were also synthesized by the application of two-directional ring-closing metathesis.
Key words
palladium catalyst - Grubbs catalyst - intramolecular cyclization - two-directional ring-closing metathesis - 5-exo-trig - benzofuran - oxepine - oxocine
- 1a
Majumdar KC.Chattopadhyay B.Ray K. Tetrahedron Lett. 2007, 48: 7633MissingFormLabel - 1b
Majumdar KC.Chattopadhyay B.Taher A. Synthesis 2007, 3647MissingFormLabel - 1c
Majumdar KC.Pal AK.Taher A.Debnath P. Synthesis 2007, 1707MissingFormLabel - 2a
Majumdar KC.Chattopadhyay B. Synlett 2008, 979MissingFormLabel - 2b
Majumdar KC.Chattopadhyay B.Nath S. Tetrahedron Lett. 2008, 49: 1319MissingFormLabel - 2c
Majumdar KC.Chakravorty S.Ray K. Synthesis 2008, 2991MissingFormLabel - 3
Majumdar KC.Sinha B.Chattopadhyay B.Ray K. Tetrahedron Lett. 2008, 49: 4405 - 4
Majumdar KC.Chattopadhyay B.Sinha B. Synthesis 2008, 3857 - 5a
Schultz DM.Prescher JA.Kidd S.Marona-Lewicka D.Nichols DE.Monte A. Bioorg. Med. Chem. 2008, 16: 6242MissingFormLabel - 5b
Rizzo S.Riviere C.Piazzi L.Bisi A.Gobbi S.Bartolini M.Andrisano V.Morroni F.Tarozzi A.Monti J.-P.Rampa A. J. Med. Chem. 2008, 51: 2883MissingFormLabel - 5c
Kirilmis C.Ahmedzade M.Servi S.Koca M.Kizirgil A.Kazaz C. Eur. J. Med. Chem. 2008, 43: 300MissingFormLabel - 5d
Ando K.Kawamura Y.Akai Y.Kunitomo J.Yokomizo T.Yamashita M.Ohta S.Ohishi T.Ohishi Y. Org. Biomol. Chem. 2008, 6: 296MissingFormLabel - 5e
Ettaoussi M.Peres B.Klupsch D.Delagrange P.Boutin J.-A.Renard P.Caignard D.-H.Chavatte P.Berthelot P.Lesieur D.Yous S. Bioorg. Med. Chem. 2008, 16: 4954MissingFormLabel - 6a
Lee Y.-K.Woo M.-H.Kim C.-H.Kim Y.Lee S.-H.Jeong B.-S.Chang H.-W.Son J.-K. Planta Med. 2007, 73: 1287MissingFormLabel - 6b
Oda K.Yamaguchi Y.Yoshimura T.Wada K.Nishizono N. Chem. Pharm. Bull. 2007, 55: 1419MissingFormLabel - 6c
Filzen GF.Bratton L.Cheng X.-M.Erasga N.Geyer A.Lee C.Lu G.Pulaski J.Sorenson RJ.Unangst PC.Trivedi BK.Xu X. Bioorg. Med. Chem. Lett. 2007, 17: 3630MissingFormLabel - 7a
Useglio M.Castellano PM.Operto MA.Torres R.Kaufman TS. Bioorg. Med. Chem. Lett. 2006, 16: 5097MissingFormLabel - 7b
Patel HJ.Sarra J.Caruso F.Rossi M.Doshi U.Stephani RA. Bioorg. Med. Chem. Lett. 2006, 16: 4644MissingFormLabel - 7c
Lazo JS.Nunes R.Skoko JJ.de Oliveira PEQ.Vogt A.Wipf P. Bioorg. Med. Chem. 2006, 14: 5643MissingFormLabel - For recent advances in the synthesis of benzofuran derivatives, see:
- 8a
Sakai N.Uchida N.Konakahara T. Tetrahedron Lett. 2008, 49: 3437MissingFormLabel - 8b
Fiandanese V.Bottalico D.Marchese G.Punzi A. Tetrahedron 2008, 64: 53MissingFormLabel - 8c
Huang X.-C.Liu YL.Liang Y.Pi S.-F.Wang F.Li J.-H. Org. Lett. 2008, 10: 1525MissingFormLabel - 8d
Nakamura I.Mizushima Y.Yamagishi U.Yamamoto Y. Tetrahedron 2007, 63: 8670MissingFormLabel - 8e
Rasool N.Rashid MA.Reinke H.Fischer C.Langer P. Tetrahedron 2007, 63: 11626MissingFormLabel - 8f
Witayakran S.Gelbaum L.Ragauskas AJ. Tetrahedron 2007, 63: 10958MissingFormLabel - 8g
Tadd AC.Fielding MR.Willis MC. Tetrahedron Lett. 2007, 48: 7578MissingFormLabel - 8h
Bekassy S.Agai B.Farkas J.Gabor E.Ferenczi M.Figueras F. Catal. Lett. 2007, 118: 219MissingFormLabel - 8i
Fakhari AR.Nematollahi D.Shamsipur M.Makarem S.Davarani SSH.Alizadeh A.Khavasi HR. Tetrahedron 2007, 63: 3894MissingFormLabel - 8j
Salih KSM.Ayoub MT.Saadeh HA.Al-Masoudi NA.Mubarak MS. Heterocycles 2007, 71: 1577MissingFormLabel - 8k
Nagamochi M.Fang Y.-Q.Lautens M. Org. Lett. 2007, 9: 2955MissingFormLabel - 8l
Rafiee M.Nematollahi D. Chem. Pharm. Bull. 2007, 55: 915MissingFormLabel - 8m
Oppenheimer J.Johnson WL.Tracey MR.Hsung RP.Yao P.-Y.Liu R.Zhao K. Org. Lett. 2007, 9: 2361MissingFormLabel - 8n
De Luca L.Giacomelli G.Nieddu G. J. Org. Chem. 2007, 72: 3955MissingFormLabel - 8o
Mattson AE.Scheidt KA. J. Am. Chem. Soc. 2007, 129: 4508MissingFormLabel - 8p
Takeda N.Miyata O.Naito T. Eur. J. Org. Chem. 2007, 149: 1509MissingFormLabel - 8q
Rao MLN.Awasthi DK.Banerjee D. Tetrahedron Lett. 2007, 48: 431MissingFormLabel - 8r
Gabriele B.Mancuso R.Salerno G.Costa M. J. Org. Chem. 2007, 72: 9278MissingFormLabel - 8s
Zhao B.Lu X. Org. Lett. 2006, 8: 5987MissingFormLabel - 8t
Santamaria A.Moreno-Manas M.Pleixats R. ARKIVOC 2007, (iv): 234MissingFormLabel - 8u
Ackermann L.Kaspar LT. J. Org. Chem. 2007, 72: 6149MissingFormLabel - 8v
Jung I.Lee JK.Song KH.Song K.Kang SO.Ko J. J. Org. Chem. 2007, 72: 3652MissingFormLabel - 8w
Bernini R.Cacchi S.De Salve I.Fabrizi G. Synthesis 2007, 873MissingFormLabel - 8x
Capozzo M.D’Auria M.Emanuele L.Racioppi R. J. Photochem. Photobiol. A. 2007, 185: 38MissingFormLabel - 8y
Anderson KW.Ikawa T.Tundel RE.Buchwald SL. J. Am. Chem. Soc. 2006, 128: 10694MissingFormLabel - 8z
Barluenga J.Vazquez-Villa H.Merino I.Ballesteros A.Gonzalez JM. Chem. Eur. J. 2006, 12: 5790MissingFormLabel - 9a
Dixit M.Sharon A.Maulik PR.Goel A. Synlett 2006, 1497MissingFormLabel - 9b
Kumar MP.Liu RS. J. Org. Chem. 2006, 71: 4951MissingFormLabel - 9c
Aslam SN.Stevenson PC.Phythian SJ.Veitch NC.Hall DR. Tetrahedron 2006, 62: 4214MissingFormLabel - 9d
Willis MC.Taylor D.Gillmore AT. Tetrahedron 2006, 62: 11513MissingFormLabel - 9e
Sanz R.Miguel D.Martinez A.Perez A. J. Org. Chem. 2006, 71: 4024MissingFormLabel - 9f
Pei LX.Li YM.Bu XZ.Gu LQ.Chan ASC. Tetrahedron Lett. 2006, 47: 2615MissingFormLabel - 9g
Carrill M.SanMartin R.Tellitu I.Dominguez E. Org. Lett. 2006, 8: 1467MissingFormLabel - 9h
Cacchi S.Fabrizi G.Goggiamani A. Curr. Org. Chem. 2006, 10: 1423MissingFormLabel - 9i
Gabriele B.Mancuso R.Salerno G.Costa M. Adv. Synth. Catal. 2006, 348: 1101MissingFormLabel - 10a
Radl S.Obadalova I. ARKIVOC 2005, (xv): 4MissingFormLabel - 10b
Bellur E.Langer P. J. Org. Chem. 2005, 70: 10013MissingFormLabel - 10c
Yao TL.Yue DW.Larock RC. J. Comb. Chem. 2005, 7: 809MissingFormLabel - 10d
Lu K.Luo TP.Xiang Z.You ZJ.Fathi R.Chen JH.Yang Z. J. Comb. Chem. 2005, 7: 958MissingFormLabel - 10e
Nakamura I.Mizushima Y.Yamamoto Y. J. Am. Chem. Soc. 2005, 127: 15022MissingFormLabel - 10f
Cruz MD.Tamariz J. Tetrahedron 2005, 61: 10061MissingFormLabel - 10g
Bellur E.Langer P. J. Org. Chem. 2005, 70: 7686MissingFormLabel - 10h
Namatollahi D.Rafiee M. Green Chem. 2005, 7: 638MissingFormLabel - 10i
Van Otterlo WAL.Morgans GL.Madeley LG.Kuzvidza S.Moleele SS.Thornton N.de Koning CB. Tetrahedron 2005, 61: 7746MissingFormLabel - 11a
Bellur E.Freifeld I.Langer P. Tetrahedron Lett. 2005, 46: 2185MissingFormLabel - 11b
Barluenga J.Vazquez-Villa H.Ballesteros A.Gonzalez JM. Adv. Synth. Catal. 2005, 347: 526MissingFormLabel - 11c
Kim KO.Tae J. Synthesis 2005, 387MissingFormLabel - 11d
Yue DW.Yao TL.Larock RC. J. Org. Chem. 2005, 70: 10292MissingFormLabel - 11e
Chen CY.Dormer PG. J. Org. Chem. 2005, 70: 6964MissingFormLabel - 11f
Colobert F.Castanet AS.Abillard O. Eur. J. Org. Chem. 2005, 3334MissingFormLabel - 11g
Sanz R.Castroviejo MP.Fernandez Y.Fananas FJ. J. Org. Chem. 2005, 70: 6548MissingFormLabel - 11h
Gabriele B.Mancuso R.Salerno G.Veltri L. Chem. Commun. 2005, 271MissingFormLabel - 12
Stefinovic M.Snieckus V. J. Org. Chem. 1998, 63: 2808 - 13a
Kishuku H.Shindo M.Shishido K. Chem. Commun. 2003, 350MissingFormLabel - 13b
Sabui SK.Venkateswaran RV. Tetrahedron Lett. 2004, 45: 983MissingFormLabel - 13c
Lecornue F.Ollivier J. Synlett 2004, 1613MissingFormLabel - 13d
Vyvyan JR.Oaksmith JM.Parks BW.Peterson EM. Tetrahedron Lett. 2005, 46: 2457MissingFormLabel - 14
Satoh Y.Libby AH.Powers C.Kowalski T.White DH.Kimble EF. Bioorg. Med. Chem. Lett. 1994, 4: 549 - 15
Kiyama R.Honma T.Hayashi K.Ogawa M.Hara M.Fujimoto M.Fujishita T. J. Med. Chem. 1995, 38: 2728 - 16
Carl KL. inventors; US Patent 4073912. ; Chem. Abstr. 1978, 89, 24156MissingFormLabel - 17a
Virolleaud M.-A.Piva O. Tetrahedron Lett. 2007, 48: 1417MissingFormLabel - 17b
Virolleaud M.Bressy AC.Piva O. Tetrahedron Lett. 2003, 44: 8081MissingFormLabel - 17c
Tsubuki M.Kanai K.Magase H.Honda T. Tetrahedron 1999, 55: 2493MissingFormLabel - 17d
Kaliappan KP.Nandurdikar RS. Chem. Commun. 2004, 2506MissingFormLabel - 17e
Schmidt B.Hermanns J. Curr. Org. Chem. 2006, 1363MissingFormLabel - 17f
Wallace DJ. Tetrahedron Lett. 2003, 44: 2145MissingFormLabel - 17g
Honda T.Ushiwata M.Mizytani H. Tetrahedron Lett. 2006, 47: 6251MissingFormLabel - 17h
Wybrow RAJ.Edwards AS.Stevenson NG.Adams H.Johnstone CJ.Harrity PA. Tetrahedron 2004, 60: 8869MissingFormLabel - 17i
Honda T.Namiki H.Kaneda K.Mizutani H. Org. Lett. 2004, 6: 87MissingFormLabel - 17j
Liddel JR. Nat. Prod. Rep. 1997, 14: 653MissingFormLabel - 17k
Ma S.Ni B.Liang Z. J. Org. Chem. 2004, 69: 6305MissingFormLabel - 17l
Fukumoto H.Takahashi K.Ishihara J.Hatakeyama S. Angew. Chem. Int. Ed. 2006, 45: 2731MissingFormLabel - 18a
Majumdar KC.Muhuri S.Rahaman H.Islam R.Roy B. Chem. Lett. 2006, 35: 1430MissingFormLabel - 18b
Majumdar KC.Rahaman H.Islam R.Roy B. Tetrahedron Lett. 2006, 47: 2111MissingFormLabel - 18c
Majumdar KC.Islam R.Rahaman H.Roy B. Org. Biomol. Chem. 2006, 4: 2393MissingFormLabel - 18d
Majumdar KC.Rahaman H.Roy B. Synlett 2006, 466MissingFormLabel - 18e
Majumdar KC.Rahaman H.Roy B. Lett. Org. Chem. 2006, 3: 526MissingFormLabel - 18f
Majumdar KC.Maji PK.Rahaman H.Roy B. Lett. Org. Chem. 2006, 3: 845MissingFormLabel - 18g
Majumdar KC.Rahaman H.Roy B. Curr. Org. Chem. 2007, 1339MissingFormLabel - 18h
Majumdar KC.Chakravorty S.Taher A. Synth. Commun. 2008, 38: 3159MissingFormLabel - 19
Chattopadhyay SK.Biswas T.Maity S. Synlett 2006, 2211 - 20a
Kong Z.-L.Tzeng S.-C.Liu Y.-C. Bioorg. Med. Chem. Lett. 2005, 15: 163MissingFormLabel - 20b
Pearson DPG.Leigh SJ.Sutherland IO. J. Chem. Soc., Perkin Trans. 1 1979, 3113MissingFormLabel - 20c
Sorrell TN.Ellis DJ. J. Org. Chem. 1985, 50: 5765MissingFormLabel