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Synthesis 2009(13): 2223-2235
DOI: 10.1055/s-0029-1216801
DOI: 10.1055/s-0029-1216801
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Diversity-Oriented Synthesis of Functionalized Diaryl Sulfones by Regioselective [3+3] Cyclizations of 1,3-Bis(siloxy)buta-1,3-dienes with 2-(Arylsulfonyl)-3-ethoxy-2-en-1-ones: Scope and Limitations
Further Information
Received
15 January 2009
Publication Date:
12 May 2009 (online)
Publication History
Publication Date:
12 May 2009 (online)
Abstract
The formal [3+3] cyclization of 1,3-bis(siloxy)buta-1,3-dienes with 2-(arylsulfonyl)-3-ethoxy-2-en-1-ones, readily available by reaction of β-keto sulfones with triethyl orthoformate, allows the synthesis of a variety of functionalized diaryl sulfones with very good regioselectivity.
Key words
arenes - sulfones - cyclizations - regioselectivity - silyl enol ethers
-
1a
Shrimali SS.Joshi BC.Kishore D. J. Indian Chem. Soc. 1988, 65: 438 -
1b
Upadhyay PS.Vansdadia RN.Baxi AJ. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1990, 29: 793 - 2
Teshirogi I.Matsutani S.Shirahase K.Fujii Y.Yoshida T. J. Med. Chem. 1996, 39: 5183 - 3
Paulini R.Lerner C.Diederich F.Jakob-Roetne R.Zuercher G.Borroni E. Helv. Chim. Acta 2006, 89: 1856 -
4a
de Benedetti PG.Iarossi D.Menziani C.Caiolfa V.Frassineti C.Cennamo C. J. Med. Chem. 1987, 30: 459 -
4b
de Benedetti PG.Iarossi D.Folli U.Frassineti C.Menziani MC.Cennamo C. J. Med. Chem. 1989, 32: 2396 - 5
Sircar I.Hoefle M.Maxwell RE. J. Med. Chem. 1983, 26: 1020 - 6
Markley LD.Tong YC.Dulworth JK.Steward DL.Goralski CT. J. Med. Chem. 1986, 29: 427 - 7
Wright J.Bolton G.Creswell M.Downing D.Georgic L. Bioorg. Med. Chem. Lett. 1996, 6: 1809 -
8a
Neamati N.Mazumder A.Zhao H.Sunder S.Burke TR.Schultz RJ.Pommier Y. Antimicrob. Agents Chemother. 1997, 41: 385 -
8b
Chan JH.Hong JS.Hunter RN.Orr GF.Cowan JR.Sherman DB.Sparks SM.Reitter BE.Andrews CW.Hazen RJ.Clair MS. J. Med. Chem. 2001, 44: 1866 -
8c
Tagat JR.McCombie SW.Steensma RW.Lin S.-I.Nazareno DV.Baroudy B.Vantuno N.Xu S.Liu J. Bioorg. Med. Chem. Lett. 2001, 11: 2143 - 9
Stanton JL.Cahill E.Dotson R.Tan J.Tomaselli HC.Wasvary JM.Stephan ZF.Steele RE. Bioorg. Med. Chem. Lett. 2000, 10: 1661 -
10a
Kozlowski JA.Zhou G.Tagat JR.Lin S.-I.McCombie SW.Ruperto VB.Duffy RA.McQuade RA.Crosby G.Taylor LA.Billard W. Bioorg. Med. Chem. Lett. 2002, 12: 791 -
10b
Wang Y.Chackalamannil S.Hu Z.Clader JW.Greenlee W.Billard W.Binch H.Crosby G.Ruperto V.Duffy RA.McQuade R.Lachowicz JE. Bioorg. Med. Chem. Lett. 2000, 10: 2247 -
10c
Boyle CD.Chackalamannil S.Chen L.-Y.Dugar S.Pushpavanam P.Billard W.Binch H.Crosby G.Cohen-Williams M.Coffin VL.Duffy RA. Bioorg. Med. Chem. Lett. 2000, 10: 2727 -
10d
Wang Y.Chackalamannil S.Chang W.Greenlee W.Ruperto V.Duffy RA.McQuade R.Lachowicz JE. Bioorg. Med. Chem. Lett. 2001, 11: 891 -
10e
Boyle CD.Chackalamannil S.Clader JW.Greenlee WJ.Josien HB.Kaminski JJ.Kozlowski JA.McCombie SW.Nazareno DV.Tagat JR.Wang Y. Bioorg. Med. Chem. Lett. 2001, 11: 2311 -
10f
Boyle CD.Vice SF.Campion J.Chackalamannil S.Lankin CM.McCombie SW.Billard W.Binch H.Crosby G.Williams M.-C.Coffin VL. Bioorg. Med. Chem. Lett. 2002, 12: 3479 - 11
Sasse A.Ligneau X.Sadek B.Elz S.Pertz HH.Ganellin CR.Arrang J.-M.Schwartz J.-C.Schunack W.Stark H. Arch. Pharm. (Weinheim, Ger.) 2001, 334: 45 - 12
Langler RF.Paddock RL.Thompson DB.Crandall I.Ciach M.Kain KC. Aust. J. Chem. 2003, 56: 1127 - 13
Clark RD.Jahangir A.Severance D.Salazar R.Chang T.Chang D.Jett MF.Smith S.Bley K. Bioorg. Med. Chem. Lett. 2004, 14: 1053 - 14
Lavey BJ.Kozlowski JA.Hipkin RW.G onsiorek W.Lundell DJ.Piwinski JJ.Narula S.Lunn CA. Bioorg. Med. Chem. Lett. 2005, 15: 783 - 15
Lu I.-L.Mahindroo N.Liang P.-H.Peng Y.-H.Kuo C.-J.Tsai K.-C.Hsieh H.-P.Chao Y.-S.Wu S.-Y. J. Med. Chem. 2006, 9: 5154 - 16
Joseph JK.Jain SL.Sain B. Synth. Commun. 2006, 36: 2743 -
17a
Chen D.-W.Kubiak RJ.Ashley JA.Janda KD. J. Chem. Soc., Perkin Trans. 1 2001, 21: 2796 -
17b
Marquie J.Laporterie A.Dubac J.Roques N.Desmurs J.-R. J. Org. Chem. 2001, 66: 421 -
17c
Repichet S.Le Roux C.Dubac J. Tetrahedron Lett. 1999, 40: 9233 -
17d
Hajipour AR.Zarei A.Khazdooz L.Pourmousavi SA.Mirjalili BBF.Ruoho AE. Phosphorus, Sulfur Silicon Relat. Elem. 2005, 180: 2029 - 18
Woroshzow V.Kutschkarow V. Zh. Obshch. Khim. 1949, 19: 1943 ; Chem. Abstr. 1950, 1922 - 19
Zhu W.Ma D. J. Org. Chem. 2005, 70: 2696 - 20
Bandgar BP.Bettigeri SV.Phopase J. Org. Lett. 2004, 6: 2105 - 21
Huang F.Batey RA. Tetrahedron 2007, 63: 7667 - 22
Erian AW.Issac Y.Sherif SM.Mahmoud FF. J. Chem. Soc., Perkin Trans. 1 2000, 3686 -
23a
Ogura K.Takeda M.Xie JR.Akazome M.Matsumoto S. Tetrahedron Lett. 2001, 42: 1923 -
23b
Matsumoto S.Kumazawa K.Ogura K. Bull. Chem. Soc. Jpn. 2003, 76: 2179 -
23c
Bianchi L.Dell’Erba C.Maccagno M.Mugnoli A.Novi M.Petrillo G.Sancassan F.Tavani C. J. Org. Chem. 2003, 68: 5254 - 24
Mutsuhiro Y.Watanabe M.Furukawa S. Chem. Pharm. Bull. 1990, 38: 902 - 25
Padwa A.Gareau Y.Harrison B.Rodriguez A. J. Org. Chem. 1992, 57: 3540 - 26
Hayakawa K.Nishiyama H.Kanematsu K. J. Org. Chem. 1985, 50: 512 - 27
Nakayama J.Hirashima A. J. Am. Chem. Soc. 1990, 112: 7648 - 28
Hu C.-M.Hong F.Jiang B.Xu Y. J. Fluorine Chem. 1994, 66: 215 - 29
Antelo B.Castedo L.Delamano J.Gomes A.Lopez C.Tojo G. J. Org. Chem. 1996, 61: 1188 - 30
Bull JR.Desmond-Smith NS.Heggie SJ.Hunter R.Tien F.-C. Synlett 1998, 900 - 31
Chan T.-H.Brownbridge P. J. Am. Chem. Soc. 1980, 102: 3534 - 32 For a review of [3+3] cyclizations
of 1,3-bis(silyl enol ethers), see:
Feist H.Langer P. Synthesis 2007, 327 - 33 For a review of the chemistry of
1,3-bis(silyl enol ethers), see:
Langer P. Synthesis 2002, 441 - 34
Riahi A.Shkoor M.Fatunsin O.Lubbe M.Reinke H.Langer P. Tetrahedron Lett. 2009, 50: 115 - 35
Molander GA.Cameron KO. J. Am. Chem. Soc. 1993, 115: 830 - 36
Nguyen VTH.Bellur E.Appel B. Synthesis 2006, 2865 -
37a
Reiter LA. J. Org. Chem. 1984, 49: 3494 -
37b
Lemcke T.Messinger P. Arch. Pharm. (Weinheim, Ger.) 1995, 328: 269 -
38a
Brownbridge P.Chan TH.Brook MA.Kang GJ. Can. J. Chem. 1983, 61: 688 -
38b
Hirai K.Ojima I. Tetrahedron Lett. 1983, 24: 785
References
All crystallographic details of this publication are contained in CCDC-717949 (4ae) and CCDC-717950 (4d), available free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html or can be ordered from the following address: Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336033; e-mail: deposit@ccdc.cam.ac.uk.