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 Nawaz; Muhammad Sher; Peter Langer

doi:10.1055/s-0030-1258559

ACCOUNT

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 Nawaz^a, Muhammad Sher^a,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

Abstract

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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

Key words

arenes - cyclizations - organosulfur compounds - silyl enol ethers

Full Text

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 H₃receptor 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