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Novel intramolecular diels-alder reactions with alkynylthio derivatives of 1,2,4-triazines. New routes to thieno[2,3-b]pyridines and thieno[2,3-c]pyridines.

✍ Scribed by Edward C. Taylor; John E. Macor

Publisher: Elsevier Science
Year: 1985
Tongue: French
Weight: 191 KB
Volume: 26
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)94842-1

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✦ Synopsis

Alkylation of 1,2,4-triazine-6-thiones with 4-iodobutyne, followed by oxidation to the sulfoxide and intramolecular cycloaddition (at room temperature), gives 2,3-dihydrothieno[2,3-c]pyridines, which are readily dehydrated with acetic anhydride to thieno[2,3_c]pyridines.

The same series of reactions carried out on 1,2,4-triazine-3-thiones leads to thieno[2,3-blpyridines.

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