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One-pot Synthesis of 1,6-Naphthyridines, Pyranopyridines and Thiopyranopyridines

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One-pot Synthesis of 1,6-Naphthyridines, Pyranopyridines and Thiopyranopyridines

Fatma K. Abdel-Wadood, Maisa I. Abdel-Monem, Atiat M. Fahmy, and Ahmed A. Geies Chemistry Department, Faculty of Science, Assiut University, Assiut 71516, Egypt

Reprint requests to Prof. Dr. Ahmed Geies. Fax: 0020882342708. E-mail: geies@aun.edu.eg Z. Naturforsch.2008,63b,303 – 312; received August 19, 2007

A one-step synthesis of [1,6]naphthyridine-2(1H)-thione (3a), pyrano[3,4-b]pyridine-2(1H)- thione (3b), thiopyrano[3,4-b]pyridine-2(1H)-thione (3c) and 6-oxoquinoline-2(1H)-thione (3d) through the reaction of benzylidene-cyanothioacetamide (1) with cyclic ketones2a–dis described.

The reaction of3a–dwith organyl chlorides yielded the 2-alkylthio-3-cyanopyridines4a–pwhich upon refluxing in ethanolic sodium ethoxide afforded the thieno[2,3-b]pyridine derivatives5a–n.

Some of the synthesized compounds were screened for the activity against bacteria and fungi.

Key words:1,6-Naphthyridine, Thienonaphthyridine, Pyranopyridine, Thiopyranopyridine

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