Synthesis of 1,3-Dihydrobenzo[c]thiophene-imines via Tandem
Reactions of o-(1-Alkynyl)benzamides
and Lawesson’s Reagent

Qiuping Ding; Xianjin Liu; Hongming Wang; Min Chen; Yiyuan Peng

doi:10.1055/s-0031-1289722

PAPER

Synthesis of 1,3-Dihydrobenzo[c]thiophene-imines via Tandem Reactions of o-(1-Alkynyl)benzamides and Lawesson’s Reagent

Qiuping Ding*^a, Xianjin Liu^a, Hongming Wang^b, Min Chen^a, Yiyuan Peng*^a
^a Key Laboratory of Functional Small Organic Molecules, Ministry of Education and College of Chemistry and Chemical Engineering, Jiangxi Normal University, 99 Ziyang Road, Nanchang 330022, P. R. of China
Fax: +86(791)88120396; e-Mail: dqpjxnu@gmail.com; e-Mail: yiyuanpeng@yahoo.com;
^b Institute for Advanced Study, Nanchang University, Nanchang, 330031, P. R. of China

Abstract

Alle Artikel dieser Rubrik

Abstract

Metal-free, one-pot tandem reactions of o-(1-alkynyl)benzamides proceed smoothly in the presence of Lawesson’s reagent leading to 1,3-dihydrobenzo[c]thiophene-imine derivatives in moderate to excellent yields under mild conditions. The method is highly regiospecific for the o-(1-alkynyl)benzothioamide, and only the five-membered-ring product is generated via a 5-exo-dig cyclization involving the sulfur atom.

Key words

o-(1-alkynyl)benzothioamides - tandem reaction - Lawesson’s reagent - metal-free - heterocycles

Volltext

Referenzen

References

1a Palkowitz AD. Glasebrook AL. Thrasher KJ. Hauser KL. Short LL. Phillips DL. Muehl BS. Sato M. Shetler PK. Cullinan GJ. Pell TR. Bryant HU. J. Med. Chem. 1997, 40: 1407

1b Cho CH. Neuenswander B. Lushington GH. Larock RC. J. Comb. Chem. 2009, 11: 900

1c Isloor AM. Kalluraya B. Pai KS. Eur. J. Med. Chem. 2010, 45: 825

1d Fakhr IMI. Radwan MAA. El-Batran S. Abd El-Salam OME. El-Shenawy SM. Eur. J. Med. Chem. 2009, 44: 1718

2a Ye B. Arnaiz DO. Chou Y. Griedel BD. Karranjawala R. Lee W. Morrissey MM. Sacchi KL. Sakata ST. Shaw KJ. Wu SC. Zhao Z. Alder M. Cheeseman S. Dole WP. Ewing J. Fitch R. Lentz D. Liang A. Light D. Morser J. Post J. Rumennik G. Subramanyam B. Sullivan ME. Vergona R. Walters J. Wang Y.-X. White KA. Whitlow M. Kochanny MJ. J. Med. Chem. 2007, 50: 2967

2b Rassu G. Zanardi F. Battistini L. Casiraghi G. Chem. Soc. Rev. 2000, 29: 109

2c Hafez HN. El-Gazzar ABA. Bioorg. Med. Chem. Lett. 2008, 18: 5222

2d Ye D. Zhang Y. Wang F. Zheng M. Zhang X. Luo X. Shen X. Jiang H. Liu H. Bioorg. Med. Chem. 2010, 18: 1773

2e Amr AEE. Sherif MH. Assy MG. Al-Omar MA. Ragab I. Eur. J. Med. Chem. 2010, 45: 5935

2f El-Kerdawy MM. El-Bendary ER. Abdel-Aziz AA.-M. El-wasseef DR. Abd El-Aziz NI. Eur. J. Med. Chem. 2010, 45: 1805

3a Anzini M. Chelini A. Mancini A. Capplli A. Frosini M. Ricci L. Valoti M. Magistretti J. Castelli L. Giordani A. Makovec F. Vomero S. J. Med. Chem. 2010, 53: 734

3b Aiello S. Wells G. Stone EL. Kadri H. Bazzi R. Bell DR. Stevens MFG. Matthews CS. Bradshaw TD. Westwell AD. J. Med. Chem. 2008, 51: 5135

3c Wang X. Sarris K. Kage K. Stewart AO. J. Med. Chem. 2009, 52: 170

3d Auria MD. Racioppi R. Viggiani L. Zanirato P. Eur. J. Org. Chem. 2009, 932

4a Plouvier B. Houssin R. Hecquet B. Colson P. Houssier C. Waring MJ. Henichart J.-P. Bailly C. Bioconjugate Chem. 1994, 5: 475

4b van Muijlwijk-Koezen JE. Timmerman H. Vollinga RC. von Drabbe Künzel JF. de Groote M. Visser S. IJzerman AP. J. Med. Chem. 2001, 44: 749

4c Mura P. Camalli M. Messori L. Piccioli F. Zanello P. Corsini M. Inorg. Chem. 2004, 43: 3863

5 Kitamura T. Takachi T. Miyaji M. Kawasato H. Taniguchi H. J. Chem. Soc., Perkin Trans. 1 1994, 1907

For recent reviews of tandem reactions, see:

6a Guo H. Ma J. Angew. Chem. Int. Ed. 2006, 45: 354

6b Tietze LF. Chem. Rev. 1996, 96: 115

6c Parsons PJ. Penkett CS. Shell AJ. Chem. Rev. 1996, 96: 195

6d Ikeda S.-I. Acc. Chem. Res. 2000, 33: 511

6e Hussain MM. Walsh PJ. Acc. Chem. Res. 2008, 41: 883

6f Sun XL. Tang Y. Acc. Chem. Res. 2008, 41: 937

7a Ding Q. He X. Wu J. J. Comb. Chem. 2009, 11: 587

7b Ding Q. Cao B. Zong Z. Peng Y. Green Chem. 2010, 12: 1607

7c Ding Q. Huang X. Wu J. J. Comb. Chem. 2009, 11: 1047

8 Liu G. Zhou Y. Ye D. Zhang D. Ding X. Jiang H. Liu H. Adv. Synth. Catal. 2009, 351: 2605

9a Ding Q. Wu J. Org. Lett. 2007, 9: 4959

9b Ding Q. Ye Y. Fan R. Wu J. J. Org. Chem. 2007, 72: 5439

9c Ding Q. Yu X. Wu J. Tetrahedron Lett. 2008, 49: 2752

9d Ding Q. Wang Z. Wu J. Tetrahedron Lett. 2009, 50: 198

9e Sun W. Ding Q. Sun X. Fan R. Wu J. J. Comb. Chem. 2007, 9: 690

10 Ding Q. Wu J. J. Comb. Chem. 2008, 10: 541

11a Koseki Y. Kusano S. Nagasaka T. Tetrahedron Lett. 1998, 39: 3517

11b Koseki Y. Omino K. Anzai S. Nagasaka T. Tetrahedron Lett. 2000, 41: 2377

11c Arcadi A. Di Giuseppe S. Marinelli F. Rossi E. Adv. Synth. Catal. 2001, 343: 443

11d van Esseveldt BCJ. Vervoort PWH. van Delft FL. Rutjes FPJT. J. Org. Chem. 2005, 70: 1791

11e Huang Q. Hunter JA. Larock RC. J. Org. Chem. 2002, 67: 3437

12a Marshall JA. Sehon CA. J. Org. Chem. 1995, 60: 5966

12b Dalla V. Pale P. New J. Chem. 1999, 23: 803

12c Oh CH. Yi HJ. Lee JH. New J. Chem. 2007, 31: 835

12d Pale P. Chuche J. Eur. J. Org. Chem. 2000, 1019

12e Yamada W. Sugawara Y. Cheng HM. Ikeno T. Yamada T. Eur. J. Org. Chem. 2007, 2604

12f Patil NT. Pahadi NK. Yamamoto Y. J. Org. Chem. 2005, 70: 10096

13 Peng A.-Y. Ding Y.-X. Org. Lett. 2005, 7: 3299

14a Clausen K. Lawesson S.-O. Bull. Soc. Chim. Belg. 1979, 88: 35

14b Clausen K. Lawesson S.-O. Nouv. J. Chem. 1980, 4: 43

Zusatzmaterial

Supporting Information