Synlett 2010(16): 2383-2391  
DOI: 10.1055/s-0030-1258559
ACCOUNT
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Organosulfur Compounds Based on Cyclocondensation Reactions of 3-Arylthio-1-silyloxy-1,3-butadienes and 1,3-Bis(silyloxy)-1,3-butadienes

Muhammad Nawaza, Muhammad Shera,b,c, Peter Langer*a,b
a Institut für Chemie, Universität Rostock, Albert-Einstein-Str. 3a, 18059 Rostock, Germany
Fax: +49(381)4986412; e-Mail: peter.langer@uni-rostock.de;
b Leibniz-Institut für Katalyse e.V. an der Universität Rostock, Albert-Einstein-Str. 29a, 18059 Rostock, Germany
c Department of Chemistry, Allama Iqbal Open University, Islamabad, Pakistan
Weitere Informationen

Publikationsverlauf

Received 5 February 2010
Publikationsdatum:
03. September 2010 (online)

Abstract

Cyclocondensation reactions of sulfur-containing dienes, such as 3-arylthio-1-silyloxy-1,3-butadienes and 4-arylthio-1,3-bis(trimethylsilyloxy)-1,3-butadienes, with various dielectrophiles and dieneophiles allow for a convenient synthesis of a variety of functionalized and sterically encumbered aryl-substituted sulfides and sulfones which are not readily available by other methods. The building block strategy outlined herein is advantageous for the synthesis of highly substituted, sterically encumbered and functionalized molecules compared to methods which rely on the formation of a carbon-sulfur bond.

1 Introduction

2 3-Arylthio-1-trimethylsilyloxy-1,3-butadienes

2.1 Synthesis of 3-Arylthio-1-trimethylsilyloxy-1,3-butadienes

2.2 [3+3] Cyclocondensations of 3-Arylthio-1-trimethylsilyl­oxy-1,3-butadienes

2.2.1 1,1,3,3-Tetramethoxypropane

2.2.2 3-Silyloxy-2-en-1-ones

2.2.3 3-Alkoxy-2-en-1-ones

2.2.4 3-Ketoacetals

2.2.5 1,1-Diacylcyclopropanes

2.2.6 3-Oxo-orthoesters

2.2.7 1,1-Bis(methylthio)-1-en-3-ones

2.3 [4+2] Cycloadditions of 1-Arylthio-3-trimethylsilyloxy-1,3-butadienes

2.3.1 Dimethyl Acetylenedicarboxylate

2.3.2 Dimethyl Allene-1,3-dicarboxylate

2.4 Michael-Type Reactions of 1-Arythio-3-trimethylsilyloxy-1,3-butadienes

3 Cyclocondensations of 1,3-Bis(silyloxy)-1,3-butadienes with Sulfur-Containing Dielectrophiles

3.1 Reactions of 3-Alkoxy- and 3-Silyloxy-2-en-1-ones

3.1.1 2-Arylthio-3-silyloxy-2-en-1-ones

3.1.2 2-Arylthio-3-alkoxy-2-en-1-ones

3.1.3 2-Arylsulfonyl-3-alkoxy-2-en-1-ones

3.2 Reactions of 1,1-Bis(methylthio)-1-en-3-ones

4 4-Arylthio-1,3-bis(trimethylsilyloxy)-1,3-butadienes

4.1 Synthesis of 4-Arylthio-1,3-bis(trimethylsilyloxy)-1,3-butadienes

4.2 [3+3] Cyclizations of 4-Arylthio-1,3-bis(trimethylsilyl­oxy)-1,3-butadienes

4.2.1 1,1,3,3-Tetramethoxypropane

4.2.2 3-Silyloxy-2-en-1-ones

4.2.3 1,1-Diacetylcyclopropane

4.3 Cyclizations of 4-Arylthio-1,3-bis(silyloxy)-1,3-butadienes with Chromones

4.3.1 Formylchromone

4.3.2 Chromone

5 Conclusions

    References

  • 1a Behar V. Danishefsky SJ. J. Am. Chem. Soc.  1993,  115:  7017 
  • 1b Toste FD. Still IWJ. J. Am. Chem. Soc.  1995,  117:  7261 
  • 1c Davidson BS. Molinski TF. Barrows LR. Ireland CM. J. Am. Chem. Soc.  1991,  113:  4709 
  • 1d Mori Y. Taneda S. Hayashi H. Sakushima A. Kamata K. Suzuki AK. Yoshino S. Sakata M. Sagai M. Seki K.-i. Biol. Pharm. Bull.  2002,  25:  145 
  • 1e Davis RA. Sandoval IT. Concepcion GP. Moreira da Rocha R. Ireland CM. Tetrahedron  2003,  59:  2855 
  • 1f Liu H. Fujiwara T. Nishikawa T. Mishima Y. Nagai H. Shida T. Tachibana K. Kobayashi H. Mangindaan REP. Namikoshi M. Tetrahedron  2005,  61:  8611 
  • 1g Kaplan ML. Reents WD. Tetrahedron Lett.  1982,  23:  373 
  • 1h Hosoya Y. Adachi H. Nakamura H. Nishimura Y. Naganawa H. Tetrahedron Lett.  1996,  37:  9227 
  • Antibacterial activity:
  • 2a Shrimali SS. Joshi BC. Kishore D. J. Indian Chem. Soc.  1988,  65:  438 
  • 2b Upadhyay PS. Vansdadia RN. Baxi AJ. Indian J. Chem. Sect. B  1990,  29:  793 
  • Inhibition of phospholipidase A2:
  • 2c Teshirogi I. Matsutani S. Shirahase K. Fujii Y. Yoshida T. J. Med. Chem.  1996,  39:  5183 
  • Inhibition of catechol O-methyltransferase:
  • 2d Paulini R. Lerner C. Diederich F. Jakob-Roetne R. Zuercher G. Borroni E. Helv. Chim. Acta  2006,  89:  1856 
  • Inhibition of dihydropteroate synthase of Escherichia coli:
  • 2e de Benedetti PG. Iarossi D. Menziani C. Caiolfa V. Frassineti C. Cennamo C. J. Med. Chem.  1987,  30:  459 
  • 2f de Benedetti PG. Iarossi D. Folli U. Frassineti C. Menziani MC. Cennamo C. J. Med. Chem.  1989,  32:  2396 
  • Hypolipidemic activity:
  • 2g Sircar I. Hoefle M. Maxwell RE. J. Med. Chem.  1983,  26:  1020 
  • Cytotoxicity against HeLa cells and the antipicornavirus:
  • 2h Markley LD. Tong YC. Dulworth JK. Steward DL. Goralski CT. J. Med. Chem.  1986,  29:  427 
  • Neuropeptide Y1 receptor binding activity:
  • 2i Wright J. Bolton G. Creswell M. Downing D. Georgic L. Bioorg. Med. Chem. Lett.  1996,  6:  1809 
  • Anti-HIV activity:
  • 2j Neamati N. Mazumder A. Zhao H. Sunder S. Burke TR. Schultz RJ. Pommier Y. Antimicrob. Agents Chemother.  1997,  41:  385 
  • 2k Chan JH. Hong JS. Hunter RN. Orr GF. Cowan JR. Sherman DB. Sparks SM. Reitter BE. Andrews CW. Hazen Richard J. Clair MS. J. Med. Chem.  2001,  44:  1866 
  • 2l 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 
  • Anticholesteremic activity:
  • 2m Stanton JL. Cahill E. Dotson R. Tan J. Tomaselli HC. Wasvary JM. Stephan ZF. Steele RE. Bioorg. Med. Chem. Lett.  2000,  10:  1661 
  • Binding to human muscarinic M1 and M2 receptors:
  • 2n 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 
  • 2o 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 
  • 2p 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 
  • 2q Wang Y. Chackalamannil S. Chang W. Greenlee W. Ruperto V. Duffy RA. McQuade R. Lachowicz JE. Bioorg. Med. Chem. Lett.  2001,  11:  891 
  • 2r 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 
  • 2s 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 
  • Histamine H3 receptor antagonistic activity:
  • 2t 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 
  • Antiprotozoal activity:
  • 2u Langler RF. Paddock RL. Thompson DB. Crandall I. Ciach M. Kain KC. Aust. J. Chem.  2003,  56:  1127 
  • Binding to neuroblastoma cells:
  • 2v 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 
  • Binding to the human cannabinoid CB1 receptor:
  • 2w Lavey BJ. Kozlowski JA. Hipkin RW. Gonsiorek W. Lundell DJ. Piwinski JJ. Narula S. Lunn CA. Bioorg. Med. Chem.  Lett. 2005,  15:  783 
  • Inhibition of the main protease of the recombinant SARS coronavirus:
  • 2x 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 
  • 3a Glass HB. Reid EE. J. Am. Chem. Soc.  1929,  51:  3428 
  • 3b Dougherty G. Hammond PD. J. Am. Chem. Soc.  1935,  57:  117 
  • For the trifluoromethanesulfonic acid catalyzed sulfurization of cycloalkanes, see:
  • 3c Olah GA. Wang Q. Prakash GKS. J. Am. Chem. Soc.  1990,  112:  3697 
  • 3d Kemp DS. Carey RI. Dewan JC. Galakatos NG. Kerkman D. Leung S.-L. J. Org. Chem.  1989,  54:  1589 ; and references cited therein
  • 3e Chua M. Hoyer H. Z. Naturforsch. B  1965,  20:  416 
  • 3f Baxter I. Ben-Haida A. Colquhoun HM. Hodge P. Kohnke FH. Williams DJ. Chem. Eur. J.  2000,  6:  4285 ; and references cited therein
  • 3g Campbell JR. J. Org. Chem.  1964,  29:  1830 
  • 4a Taniguchi N. J. Org. Chem.  2007,  72:  1241 
  • 4b Fernández-Rodríguez MA. Shen Q. Hartwig JF. J. Am. Chem. Soc.  2006,  128:  2180 
  • 4c Murata M. Buchwald SL. Tetrahedron  2004,  60:  7397 
  • 4d Gendre F. Yang M. Diaz P. Org. Lett.  2005,  7:  2719 
  • 4e Bates CG. Gujadhur RK. Venkataraman D. Org. Lett.  2002,  4:  2803 
  • 4f Rábai J. Synthesis  1989,  523 
  • 5a Joseph JK. Jain SL. Sain B. Synth. Commun.  2006,  36:  2743 
  • 5b Chen D.-W. Kubiak RJ. Ashley JA. Janda KD. J. Chem. Soc., Perkin Trans. 1  2001,  21:  2796 
  • 5c Marquie J. Laporterie A. Dubac J. Roques N. Desmurs J.-R. J. Org. Chem.  2001,  66:  421 
  • 5d Repichet S. Roux CL. Dubac J. Tetrahedron Lett.  1999,  40:  9233 
  • 5e Hajipour AR. Zarei A. Khazdooz L. Pourmousavi SA. Mirjalili BBF. Ruoho AE. Phosphorus Sulfur Silicon Relat. Elem.  2005,  180:  2029 
  • 5f Woroshzow V. Kutschkarow V. Zh. Obshch. Khim.  1949,  19:  1943 ; Chem. Abstr. 1950, 1922
  • 6a Zhu W. Ma D. J. Org. Chem.  2005,  70:  2696 
  • 6b Bandgar BP. Bettigeri SV. Phopase J. Org. Lett.  2004,  6:  2105 
  • 6c Huang F. Batey RA. Tetrahedron  2007,  63:  7667 
  • 7a Hilt G. Lüers S. Synthesis  2003,  1784 
  • 7b Hilt G. Lüers S. Harms K. J. Org. Chem.  2004,  69:  624 
  • 8a Erian AW. Issac Y. Sherif SM. Mahmoud FF. J. Chem. Soc., Perkin Trans. 1  2000,  3686 
  • 8b Ogura K. Takeda M. Xie JR. Akazome M. Matsumoto S. Tetrahedron Lett.  2001,  42:  1923 
  • 8c Matsumoto S. Kumazawa K. Ogura K. Bull. Chem. Soc. Jpn.  2003,  76:  2179 
  • 8d Bianchi L. Dell’Erba C. Maccagno M. Mugnoli A. Novi M. Petrillo G. Sancassan F. Tavani C. J. Org. Chem.  2003,  68:  5254 
  • 8e Mutsuhiro Y. Watanabe M. Furukawa S. Chem. Pharm. Bull.  1990,  38:  902 
  • 8f Padwa A. Gareau Y. Harrison B. Rodriguez A. J. Org. Chem.  1992,  57:  3540 
  • 8g Hayakawa K. Nishiyama H. Kanematsu K. J. Org. Chem.  1985,  50:  512 
  • 8h Nakayama J. Hirashima A. J. Am. Chem. Soc.  1990,  112:  7648 
  • 8i Hu C.-M. Hong F. Jiang B. Xu Y. J. Fluorine Chem.  1994,  66:  215 
  • 8j Antelo B. Castedo L. Delamano J. Gomes A. Lopez C. Tojo G. J. Org. Chem.  1996,  61:  1188 
  • 8k Bull JR. Desmond-Smith NS. Heggie SJ. Hunter R. Tien F.-C. Synlett  1998,  900 
  • 9 Chan TH. Prasad CVC. J. Org. Chem.  1986,  51:  3012 
  • 10 Imran M. Iqbal I. Rasool N. Rashid MA. Langer P. Synlett  2008,  2708 
  • 11 Imran M. Iqbal I. Rasool N. Fischer C. Langer P. Tetrahedron  2009,  65:  8794 
  • 12 Iqbal I. Imran M. Langer P. Helv. Chim. Acta  2010,  in print
  • 13 Iqbal I. Imran M. Shkoor M. Fatunsin O. Riahi A. Villinger A. Fischer C. Langer P. Tetrahedron  2010,  submitted
  • 14 Iqbal I. Imran M. Villinger A. Langer P. Synthesis  2009,  297 
  • 15 Andersson C.-M. Hallberg A. J. Org. Chem.  1988,  53:  4257 
  • 16 Rashid MA. Rasool N. Iqbal I. Imran M. Langer P. Tetrahedron Lett.  2008,  49:  2466 
  • 17 Danishefsky SJ. Acc. Chem. Res.  1979,  66 
  • 18 Zefirov NS. Kozhushkov SI. Kuznetsova TS. Tetrahedron  1982,  38:  1693 
  • 19 Imran M. Iqbal I. Langer P. Synlett  2009,  1477 
  • 20 Iqbal I. Imran M. Langer P. Synthesis  2009,  2430 
  • 21 Iqbal I. Imran M. Fischer C. Langer P. Helv. Chim. Acta  2010,  93:  704 
  • 22a Prasad CVC. Chan TH. J. Org. Chem.  1987,  52:  110 
  • 22b Prasad CVC. Chan TH. J. Org. Chem.  1987,  52:  120 
  • 22c Prasad CVC. Chan TH. J. Org. Chem.  1989,  54:  3242 
  • 22d Schwerdtfeger AE. Chan TH.
    J. Org. Chem.  1993,  58:  6513 
  • 23a Chan T.-H. Brownbridge P. J. Am. Chem. Soc.  1980,  102:  3534 
  • 23b Brownbridge P. Chan T.-H. Brook MA. Kang GJ. Can. J. Chem.  1983,  61:  688 
  • 24 For a review on [3+3] cyclocondensations of 1,3-bis(silyl enol ethers) with 1,3-dielectrophiles, see: Feist H. Langer P. Synthesis  2007,  327 
  • 25 Rashid MA. Reinke H. Langer P. Tetrahedron Lett.  2007,  48:  2321 
  • 26 Rashid MA. Rasool N. Adeel M. Reinke H. Fischer C. Langer P. Tetrahedron  2008,  64:  3782 
  • 27 Shkoor M. Fatunsin O. Riahi A. Villinger A. Langer P. Tetrahedron Lett.  2009,  50:  5726 
  • 28 Fatunsin O. Shkoor M. Riahi A. Hussain M. Villinger A. Fischer C. Langer P. Helv. Chim. Acta  2010,  in print
  • 29 Riahi A. Shkoor M. Fatunsin O. Lubbe M. Reinke H. Langer P. Tetrahedron Lett.  2009,  50:  115 
  • 30 Shkoor M. Riahi A. Fatunsin O. Reinke H. Fischer C. Langer P. Synthesis  2009,  2223 
  • 31 Lubbe M. Klassen R. Trabhardt T. Villinger A. Langer P. Synlett  2008,  2331 
  • 32 Sher M. Ahmed Z. Rashid MA. Fischer C. Langer P. J. Org. Chem.  2007,  72:  6284 
  • 33 Appel B. Rotzoll S. Reinke H. Langer P. Eur. J. Org. Chem.  2006,  3638 
  • 34 Appel B. Saleh NNR. Langer P. Chem. Eur. J.  2006,  12:  1221