Synthesis of 3-Arylthieno[2,3-b]-, -[2,3-c]- or -[3,2-c]pyridines Utilizing an Interrupted
Pummerer Reaction

Kazuhiro Kobayashi; Teruhiko Suzuki; Mai Horiuchi; Yasuhiko Shiroyama; Hisatoshi Konishi

doi:10.1055/s-0030-1260152

PAPER

Synthesis of 3-Arylthieno[2,3-b]-, -[2,3-c]- or -[3,2-c]pyridines Utilizing an Interrupted Pummerer Reaction

Kazuhiro Kobayashi*, Teruhiko Suzuki, Mai Horiuchi, Yasuhiko Shiroyama, Hisatoshi Konishi
Division of Applied Chemistry, Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, 4-101 Koyama-minami, Tottori 680-8552, Japan
Fax: +81(857)315263; e-Mail: kkoba@chem.tottori-u.ac.jp;

Abstract

Alle Artikel dieser Rubrik

Abstract

An efficient procedure for the synthesis of three types of thienopyridines has been developed. Thus, 3-(1-arylethenyl)-2-(ethylsulfinyl)pyridines, 4-(1-arylethenyl)-3-(ethylsulfinyl)pyridines, and 3-(1-arylethenyl)-4-(ethylsulfinyl)pyridines, which can be easily prepared from the respective aryl chloropyridinyl ketones in a three-step sequence, undergo an interrupted Pummerer reaction on treatment with excess acetic anhydride at temperatures ranging from 100 to 130 ˚C to give 3-arylthieno[2,3-b]pyridines, 3-arylthieno[2,3-c]pyridines, and 3-arylthieno[3,2-c]pyridines, respectively.

Key words

thieno[2,3-b]pyridines - thieno[2,3-c]pyridines - thieno[3,2-c]pyridines - interrupted Pummerer reaction - acetic anhydride

Volltext

Referenzen

References

For reports on the biological activity of thieno[2,3-b]pyridine derivatives:

1a Wu B. Boscelli DH. Lee J. Yang X. Chaudhary D. Bioorg. Med. Chem. Lett. 2009, 19: 766

1b Wu JP. Fleck R. Brickwood J. Capolino A. Catron K. Chen Z. Cywin C. Emeigh J. Foerst M. Ginn J. Hrapchak M. Hickey E. Hao M.-H. Kashem M. Li J. Liu W. Morwick T. Nelson R. Marshall D. Martin L. Nemoto P. Potocki I. Liuzzi M. Peet GW. Scouten E. Stefany D. Turner M. Weldon S. Zimmitti C. Spero D. Kelly TA. Bioorg. Med. Chem. Lett. 2009, 19: 5547

1c Gad-Elkareem MAM. El-Adasy A.-BAAM. Phosphorus, Sulfur Silicon Relat. Elem. 2010, 185: 411

1d Lockman JW. Reeder MD. Suzuki K. Orstanin K. Hoff R. Bhoite L. Austin H. Baichwal V. Willardsen JA. Bioorg. Med. Chem. Lett. 2010, 20: 2283

1e Zheng X.-X. Zheng R.-L. Zhou T. He H.-Y. Liu J.-Y. Zheng Y. Tong A.-P. Xiang M.-L. Song X.-R. Yang S.-Y. Yu L.-T. Wei Y.-Q. Zhao Y.-L. Bioorg. Med. Chem. Lett. 2010, 20: 6282

1f Taltavull J. Serrat J. Grácia J. Gavaldá A. Andrés M. Córdoba M. Miralpeix M. Viella D. Beleta J. Ryder H. Pagés L.
J. Med. Chem. 2010, 53: 6912

1g Pevet I. Brulé C. Tizot A. Gohier A. Cryzalegui F. Boutin JA. Bioorg. Med. Chem. 2011, 19: 2517

1h

See also pertinent references cited in ref. 11.

For reports on the biological activity of thieno[2,3-c]pyri-dine derivatives:

2a Zhu G.-D. Andersen DL. Gunawardana IW. Boyd SA. Stewart AO. Fry DG. Cool BL. Kifle L. Schaefer V. Meuth J. Marsh KC. Kempf-Grote AJ. Kilgannon P. Gallatin WM. Okasinski GF. J. Med. Chem. 2001, 44: 3469

2b Romagnoli R. Baraldi PG. Moorman AR. Iaconinoto MA. Carrion MD. Cara CL. Tabrizi MA. Preti D. Fruttarolo F. Baker SP. Varani K. Borea PA. Bioorg. Med. Chem. Lett. 2006, 16: 5530

2c George D. Friedman M. Allen H. Argiriadi M. Barberis C. Bischoff A. Clabbers A. Cusack K. Dixon R. Fix-Stenzel S. Gordon T. Janssen B. Jia Y. Moskey M. Quinn C. Salmeron J.-A. Wishart N. Woller K. Zu Z. Bioorg. Med. Chem. Lett. 2008, 18: 4952

2d Cusack K. Allen H. Bischoff A. Clabbers A. Dixon R. Fix-Stenzel S. Friedman M. Gaumont Y. George D. Gordon T. Grongsaard P. Janssen B. Jia Y. Moskey M. Quinn C. Salmeron A. Thomas C. Wallace G. Wishart N. Yu Z. Bioorg. Med. Chem. Lett. 2009, 19: 1722

2e Zhao L. Zhang Y. Dai C. Guzi T. Wiswell D. Seghezzi W. Parry D. Fischmann T. Siddiqui MA. Bioorg. Med. Chem. Lett. 2010, 20: 7216

2f