Annulated 1,2,4-Triazoles. A Convenient Synthesis of Thieno[2,3-f][1,2,4]triazolo[1,5-a]azepines: A Novel Triheterocyclic Ring System

Quanrui Wang; Zheng Li; Haiyan Yang; Feng Li; Zongbiao Ding; Fenggang Tao

doi:10.1055/s-2003-39392

PAPER

Annulated 1,2,4-Triazoles. A Convenient Synthesis of Thieno[2,3-f][1,2,4]triazolo[1,5-a]azepines: A Novel Triheterocyclic Ring System

Quanrui Wang*, Zheng Li, Haiyan Yang, Feng Li, Zongbiao Ding, Fenggang Tao
Department of Chemistry, Fudan University, 200433 Shanghai, P. R. China
Fax: +86(21)65641740; e-Mail: qrwangb@online.sh.cn;

Abstract

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Abstract

A synthetic approach to the previously unknown thieno[2,3-f][1,2,4]triazolo[1,5-a]azepine derivatives was efficiently accomplished by cycloaddition of the bicyclic 1-aza-2-azoniaallene salts 6, derived from 6,7-dihydrobenzo[b]thiophen-4(5H)-one hydrazones 4, to the triple bond of nitriles, followed by ring enlargement. The X-ray crystal diffraction analysis of the picrate 10a provided affirmative proof for the structural assignment made.

Key words

1-aza-2-azoniaallene cations - cycloaddition - nitriles - ring enlargement - thieno[2,3-f][1,2,4]triazolo[1,5-a]azepines

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References

1 Moriwaki M, Kawakami Y, Koga Y, Okamoto H, and Terasawa M. inventors; Jpn. Kokai Tokkyo Koho JP 05345785. ; Chem. Abstr. 1994, 121, 300897

2 Yamamoto Y, Shindo M, and Nakamura T. inventors; PCT Int. Appl. WO 9747622. ; Chem. Abstr. 1998, 128, 75427

3 Tanaka H, Kuroita T, Ishibuchi S, Ushio H, Futamura T, Ohasha Y, and Yano K. inventors; PCT Int. Appl. WO 9703986. ; Chem. Abstr. 1997, 126, 199585

4 Janssens FE, Lacrampe JFA, and Pilatte INC. inventors; PCT Int. Appl. WO 9413681. ; Chem. Abstr. 1994, 121, 205360

5 Tanaka H. Nakao T. J. Heterocycl. Chem. 1997, 34: 921

6 Gu ZQ. Wong G. Dominguez C. de-Costa BR. Rice KC. Skolnick P. J. Med. Chem. 1993, 36: 1001

7 Kawakami Y. Kitani H. Yuasa S. Abe M. Moriwaki M. Kagoshima M. Terasawa M. Tahara T. Eur. J. Med. Chem. 1996, 31: 683

8 Liu X. Liu Y. Wang Q. Zou J. Synth. Commun. 2000, 30: 119

9 Wang Q. Liu X. Li F. Ding Z. Tao F. Synth. Commun. 2002, 32: 1327

10 Liu X. Wang Q. Liu Y. Fan Y. Ding Z. Synthesis 2000, 435

11 Cho H. Matsuki S. Heterocycles 1996, 43: 127

12 Fieser LF. Kennelly RG. J. Am. Chem. Soc. 1935, 57: 1611

13 Napier RP. Chu C. Int. J. Sulfur Chem., Part A 1971, 1: 62

14 Kajigaeshi S. Kakinami T. Moriwaki M. Fujisaki S. Maeno K. Okamoto T. Synthesis 1989, 545

15 Gstach H. Seil P. Synthesis 1990, 803

16 Wang Q. Jochims JC. Köhlbrandt S. Dahlenburg L. Al-Talib M. Hamed A. Ismail AE. Synthesis 1992, 710

17 Allen FH. Kennard O. Watson DG. Brammer L. Orpen AG. Taylor R. J. Chem. Soc., Perkin Trans. 2 1987, 12: S1

18 Dewar MJS. Thiel W. J. Am. Chem. Soc. 1977, 99: 4907

19 Ding Z. Xia S. Ji X. Yang H. Tao F. Wang Q. Synthesis 2002, 349

20 Mintz MJ. Walling C. Org. Synth., Coll. Vol. V Wiley; New York: 1973. p.184