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Synthesis 2009(4): 674-680
DOI: 10.1055/s-0028-1083339
DOI: 10.1055/s-0028-1083339
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
An 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)
![](https://www.thieme-connect.de/media/synthesis/200904/lookinside/thumbnails/10.1055-s-0028-1083339-1.jpg)
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: 7633 -
1b
Majumdar KC.Chattopadhyay B.Taher A. Synthesis 2007, 3647 -
1c
Majumdar KC.Pal AK.Taher A.Debnath P. Synthesis 2007, 1707 -
2a
Majumdar KC.Chattopadhyay B. Synlett 2008, 979 -
2b
Majumdar KC.Chattopadhyay B.Nath S. Tetrahedron Lett. 2008, 49: 1319 -
2c
Majumdar KC.Chakravorty S.Ray K. Synthesis 2008, 2991 - 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: 6242 -
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: 2883 -
5c
Kirilmis C.Ahmedzade M.Servi S.Koca M.Kizirgil A.Kazaz C. Eur. J. Med. Chem. 2008, 43: 300 -
5d
Ando K.Kawamura Y.Akai Y.Kunitomo J.Yokomizo T.Yamashita M.Ohta S.Ohishi T.Ohishi Y. Org. Biomol. Chem. 2008, 6: 296 -
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: 4954 -
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: 1287 -
6b
Oda K.Yamaguchi Y.Yoshimura T.Wada K.Nishizono N. Chem. Pharm. Bull. 2007, 55: 1419 -
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: 3630 -
7a
Useglio M.Castellano PM.Operto MA.Torres R.Kaufman TS. Bioorg. Med. Chem. Lett. 2006, 16: 5097 -
7b
Patel HJ.Sarra J.Caruso F.Rossi M.Doshi U.Stephani RA. Bioorg. Med. Chem. Lett. 2006, 16: 4644 -
7c
Lazo JS.Nunes R.Skoko JJ.de Oliveira PEQ.Vogt A.Wipf P. Bioorg. Med. Chem. 2006, 14: 5643 - For recent advances in the synthesis of benzofuran derivatives, see:
-
8a
Sakai N.Uchida N.Konakahara T. Tetrahedron Lett. 2008, 49: 3437 -
8b
Fiandanese V.Bottalico D.Marchese G.Punzi A. Tetrahedron 2008, 64: 53 -
8c
Huang X.-C.Liu YL.Liang Y.Pi S.-F.Wang F.Li J.-H. Org. Lett. 2008, 10: 1525 -
8d
Nakamura I.Mizushima Y.Yamagishi U.Yamamoto Y. Tetrahedron 2007, 63: 8670 -
8e
Rasool N.Rashid MA.Reinke H.Fischer C.Langer P. Tetrahedron 2007, 63: 11626 -
8f
Witayakran S.Gelbaum L.Ragauskas AJ. Tetrahedron 2007, 63: 10958 -
8g
Tadd AC.Fielding MR.Willis MC. Tetrahedron Lett. 2007, 48: 7578 -
8h
Bekassy S.Agai B.Farkas J.Gabor E.Ferenczi M.Figueras F. Catal. Lett. 2007, 118: 219 -
8i
Fakhari AR.Nematollahi D.Shamsipur M.Makarem S.Davarani SSH.Alizadeh A.Khavasi HR. Tetrahedron 2007, 63: 3894 -
8j
Salih KSM.Ayoub MT.Saadeh HA.Al-Masoudi NA.Mubarak MS. Heterocycles 2007, 71: 1577 -
8k
Nagamochi M.Fang Y.-Q.Lautens M. Org. Lett. 2007, 9: 2955 -
8l
Rafiee M.Nematollahi D. Chem. Pharm. Bull. 2007, 55: 915 -
8m
Oppenheimer J.Johnson WL.Tracey MR.Hsung RP.Yao P.-Y.Liu R.Zhao K. Org. Lett. 2007, 9: 2361 -
8n
De Luca L.Giacomelli G.Nieddu G. J. Org. Chem. 2007, 72: 3955 -
8o
Mattson AE.Scheidt KA. J. Am. Chem. Soc. 2007, 129: 4508 -
8p
Takeda N.Miyata O.Naito T. Eur. J. Org. Chem. 2007, 149: 1509 -
8q
Rao MLN.Awasthi DK.Banerjee D. Tetrahedron Lett. 2007, 48: 431 -
8r
Gabriele B.Mancuso R.Salerno G.Costa M. J. Org. Chem. 2007, 72: 9278 -
8s
Zhao B.Lu X. Org. Lett. 2006, 8: 5987 -
8t
Santamaria A.Moreno-Manas M.Pleixats R. ARKIVOC 2007, (iv): 234 -
8u
Ackermann L.Kaspar LT. J. Org. Chem. 2007, 72: 6149 -
8v
Jung I.Lee JK.Song KH.Song K.Kang SO.Ko J. J. Org. Chem. 2007, 72: 3652 -
8w
Bernini R.Cacchi S.De Salve I.Fabrizi G. Synthesis 2007, 873 -
8x
Capozzo M.D’Auria M.Emanuele L.Racioppi R. J. Photochem. Photobiol. A. 2007, 185: 38 -
8y
Anderson KW.Ikawa T.Tundel RE.Buchwald SL. J. Am. Chem. Soc. 2006, 128: 10694 -
8z
Barluenga J.Vazquez-Villa H.Merino I.Ballesteros A.Gonzalez JM. Chem. Eur. J. 2006, 12: 5790 -
9a
Dixit M.Sharon A.Maulik PR.Goel A. Synlett 2006, 1497 -
9b
Kumar MP.Liu RS. J. Org. Chem. 2006, 71: 4951 -
9c
Aslam SN.Stevenson PC.Phythian SJ.Veitch NC.Hall DR. Tetrahedron 2006, 62: 4214 -
9d
Willis MC.Taylor D.Gillmore AT. Tetrahedron 2006, 62: 11513 -
9e
Sanz R.Miguel D.Martinez A.Perez A. J. Org. Chem. 2006, 71: 4024 -
9f
Pei LX.Li YM.Bu XZ.Gu LQ.Chan ASC. Tetrahedron Lett. 2006, 47: 2615 -
9g
Carrill M.SanMartin R.Tellitu I.Dominguez E. Org. Lett. 2006, 8: 1467 -
9h
Cacchi S.Fabrizi G.Goggiamani A. Curr. Org. Chem. 2006, 10: 1423 -
9i
Gabriele B.Mancuso R.Salerno G.Costa M. Adv. Synth. Catal. 2006, 348: 1101 -
10a
Radl S.Obadalova I. ARKIVOC 2005, (xv): 4 -
10b
Bellur E.Langer P. J. Org. Chem. 2005, 70: 10013 -
10c
Yao TL.Yue DW.Larock RC. J. Comb. Chem. 2005, 7: 809 -
10d
Lu K.Luo TP.Xiang Z.You ZJ.Fathi R.Chen JH.Yang Z. J. Comb. Chem. 2005, 7: 958 -
10e
Nakamura I.Mizushima Y.Yamamoto Y. J. Am. Chem. Soc. 2005, 127: 15022 -
10f
Cruz MD.Tamariz J. Tetrahedron 2005, 61: 10061 -
10g
Bellur E.Langer P. J. Org. Chem. 2005, 70: 7686 -
10h
Namatollahi D.Rafiee M. Green Chem. 2005, 7: 638 -
10i
Van Otterlo WAL.Morgans GL.Madeley LG.Kuzvidza S.Moleele SS.Thornton N.de Koning CB. Tetrahedron 2005, 61: 7746 -
11a
Bellur E.Freifeld I.Langer P. Tetrahedron Lett. 2005, 46: 2185 -
11b
Barluenga J.Vazquez-Villa H.Ballesteros A.Gonzalez JM. Adv. Synth. Catal. 2005, 347: 526 -
11c
Kim KO.Tae J. Synthesis 2005, 387 -
11d
Yue DW.Yao TL.Larock RC. J. Org. Chem. 2005, 70: 10292 -
11e
Chen CY.Dormer PG. J. Org. Chem. 2005, 70: 6964 -
11f
Colobert F.Castanet AS.Abillard O. Eur. J. Org. Chem. 2005, 3334 -
11g
Sanz R.Castroviejo MP.Fernandez Y.Fananas FJ. J. Org. Chem. 2005, 70: 6548 -
11h
Gabriele B.Mancuso R.Salerno G.Veltri L. Chem. Commun. 2005, 271 - 12
Stefinovic M.Snieckus V. J. Org. Chem. 1998, 63: 2808 -
13a
Kishuku H.Shindo M.Shishido K. Chem. Commun. 2003, 350 -
13b
Sabui SK.Venkateswaran RV. Tetrahedron Lett. 2004, 45: 983 -
13c
Lecornue F.Ollivier J. Synlett 2004, 1613 -
13d
Vyvyan JR.Oaksmith JM.Parks BW.Peterson EM. Tetrahedron Lett. 2005, 46: 2457 - 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, 24156 -
17a
Virolleaud M.-A.Piva O. Tetrahedron Lett. 2007, 48: 1417 -
17b
Virolleaud M.Bressy AC.Piva O. Tetrahedron Lett. 2003, 44: 8081 -
17c
Tsubuki M.Kanai K.Magase H.Honda T. Tetrahedron 1999, 55: 2493 -
17d
Kaliappan KP.Nandurdikar RS. Chem. Commun. 2004, 2506 -
17e
Schmidt B.Hermanns J. Curr. Org. Chem. 2006, 1363 -
17f
Wallace DJ. Tetrahedron Lett. 2003, 44: 2145 -
17g
Honda T.Ushiwata M.Mizytani H. Tetrahedron Lett. 2006, 47: 6251 -
17h
Wybrow RAJ.Edwards AS.Stevenson NG.Adams H.Johnstone CJ.Harrity PA. Tetrahedron 2004, 60: 8869 -
17i
Honda T.Namiki H.Kaneda K.Mizutani H. Org. Lett. 2004, 6: 87 -
17j
Liddel JR. Nat. Prod. Rep. 1997, 14: 653 -
17k
Ma S.Ni B.Liang Z. J. Org. Chem. 2004, 69: 6305 -
17l
Fukumoto H.Takahashi K.Ishihara J.Hatakeyama S. Angew. Chem. Int. Ed. 2006, 45: 2731 -
18a
Majumdar KC.Muhuri S.Rahaman H.Islam R.Roy B. Chem. Lett. 2006, 35: 1430 -
18b
Majumdar KC.Rahaman H.Islam R.Roy B. Tetrahedron Lett. 2006, 47: 2111 -
18c
Majumdar KC.Islam R.Rahaman H.Roy B. Org. Biomol. Chem. 2006, 4: 2393 -
18d
Majumdar KC.Rahaman H.Roy B. Synlett 2006, 466 -
18e
Majumdar KC.Rahaman H.Roy B. Lett. Org. Chem. 2006, 3: 526 -
18f
Majumdar KC.Maji PK.Rahaman H.Roy B. Lett. Org. Chem. 2006, 3: 845 -
18g
Majumdar KC.Rahaman H.Roy B. Curr. Org. Chem. 2007, 1339 -
18h
Majumdar KC.Chakravorty S.Taher A. Synth. Commun. 2008, 38: 3159 - 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: 163 -
20b
Pearson DPG.Leigh SJ.Sutherland IO. J. Chem. Soc., Perkin Trans. 1 1979, 3113 -
20c
Sorrell TN.Ellis DJ. J. Org. Chem. 1985, 50: 5765