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

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Synthesis 2012(6): 920-926
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

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Publikationsverlauf

Received 8 November 2011
Publikationsdatum:
27. Februar 2012 (online)

Abstract
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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

Supporting Information

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

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

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

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

Suche in Google Scholar
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

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

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

Suche in Google Scholar
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

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

Suche in Google Scholar
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

Suche in Google Scholar
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

Suche in Google Scholar
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

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

Suche in Google Scholar
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

Suche in Google Scholar
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

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

Suche in Google Scholar
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

Suche in Google Scholar
6b Tietze LF. Chem. Rev. 1996, 96: 115

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

Suche in Google Scholar
6d Ikeda S.-I. Acc. Chem. Res. 2000, 33: 511

Suche in Google Scholar
6e Hussain MM. Walsh PJ. Acc. Chem. Res. 2008, 41: 883

Suche in Google Scholar
6f Sun XL. Tang Y. Acc. Chem. Res. 2008, 41: 937

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

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

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

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

Suche in Google Scholar
9a Ding Q. Wu J. Org. Lett. 2007, 9: 4959

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

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

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

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

Suche in Google Scholar
10 Ding Q. Wu J. J. Comb. Chem. 2008, 10: 541

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

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

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

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

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

Suche in Google Scholar
12a Marshall JA. Sehon CA. J. Org. Chem. 1995, 60: 5966

Suche in Google Scholar
12b Dalla V. Pale P. New J. Chem. 1999, 23: 803

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

Suche in Google Scholar
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

Suche in Google Scholar
13 Peng A.-Y. Ding Y.-X. Org. Lett. 2005, 7: 3299

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

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

Suche in Google Scholar

Zusatzmaterial

Supporting Information