Synthesis 2014; 46(17): 2317-2326
DOI: 10.1055/s-0033-1339138
paper
© Georg Thieme Verlag Stuttgart · New York

A Novel Way to Tricyclic Heteroaromatics; Thiazolo[5,4-b]thieno[3,2-e]pyridine Derivatives

Authors

  • Liye Huang

    a   School of Chemistry and Chemical Engineering, Sun Yat-sen University, Guangzhou 510275, P. R. of China   Fax: +86(20)84113610   Email: ceswyq@mail.sysu.edu.cn
  • Ruina Yu

    a   School of Chemistry and Chemical Engineering, Sun Yat-sen University, Guangzhou 510275, P. R. of China   Fax: +86(20)84113610   Email: ceswyq@mail.sysu.edu.cn
  • Ling Leng

    b   Institute of Blood Transfusion, Department of Molecular Biology, Beijing 100850   P. R. of China
  • Feng Gong

    b   Institute of Blood Transfusion, Department of Molecular Biology, Beijing 100850   P. R. of China
  • Xinhai Zhu*

    a   School of Chemistry and Chemical Engineering, Sun Yat-sen University, Guangzhou 510275, P. R. of China   Fax: +86(20)84113610   Email: ceswyq@mail.sysu.edu.cn
  • Yiqian Wan*

    a   School of Chemistry and Chemical Engineering, Sun Yat-sen University, Guangzhou 510275, P. R. of China   Fax: +86(20)84113610   Email: ceswyq@mail.sysu.edu.cn
Further Information

Publication History

Received: 15 March 2014

Accepted after revision: 27 April 2014

Publication Date:
12 June 2014 (online)


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Abstract

Thiazolo[5,4-b]thieno[3,2-e]pyridine derivatives, novel tricyclic heteroaromatics, have been designed and synthesized by a one-pot reaction of diazepinethiones and aldehydes. This reaction is based on a novel rearrangement reaction of seven-membered 1,4-diazepine-2-thiones to six-membered 3-aminopyridine-2-thiols catalyzed by scandium(III) triflate.

Supporting Information