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Z. Naturforsch. 2014,
69b, 509 – 518
doi:10.5560/ZNB.2014-3320
Synthesis of Methyl 3-Azidothieno[2,3-b]pyridine-2-carboxylates and Application of the Huisgen Reaction
1 SRMSC (LIMBP), UMR 7565 Institut Jean Barriol, Université de Lorraine, 1 Boulevard Arago, 57070 Metz, France
2 Laboratoire de Chimie Bioorganique et Analytique (LCBA), FST-Mohammedia, BP 146, 20800 Mohammedia, Maroc
3 Actual address: Institut de Chimie, Faculté des Sciences, Université d'Annaba, 23000 Annaba, Algérie
Reprint requests to Prof Gilbert Kirsch. Fax: +33 387315801. E-mail:
gilbert.kirsch@univ-lorraine.fr
Received December 4, 2013 / published online May 7, 2014
Dedicated to Professor Willi Kantlehner on the occasion of his 70thbirthday for his longtime involvement and promotion of the chemistry of iminium salts
The preparation of new substituted methyl 3-azidothieno[2,3-b]pyridine carboxylates by azotization of methyl 3-aminothieno[2,3-b]pyridine and subsequent treatment with sodium azide is described. Via Huisgen's 1,3-dipolar cycloaddition between substituted alkynes and the prepared azides, methyl 1,2,3-triazolo-thieno[2,3-b]pyridine carboxylates have been obtained.
Key words: Vilsmeier-Haack-Arnold Reaction, 2-Chloro-3-cyano-pyridines, Thienopyridines, 1,2,3-Triazole