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A NOVEL ACCESS TO SOME 1,4-DICHLOROISOQUINOLINES FROM PHENACYL AZIDES

The Vilsmeier-Haack reaction initially used for the formylation of activated aromatic substrates' and carbonyl compounds2 has now evolved into a powerful synthetic tool for the construction of many heterocyclic compounds3 such as quinolines, indoles, quinazolines, pyridines, etc. In continuation of our previous work on exploring the use of bis(trichloromethy1) carbonate (BTC) in organic synthesis: we focused our research on the use of Vilsmeier salts derived from BTC and N,N-dimethylfomamide (DMF).5 Herein we describe a mild and efficient one-step synthesis of substituted 1,4-dichloroisoquinolines and 5-aryloxazole-4-carboxaldehydes from various phenacyl azides under Vilsmeier conditions.