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Communication | Regular issue | Vol 19, No. 11, 1982, pp.2071-2074
Published online, 1st January, 1970
DOI: 10.3987/R-1982-11-2071
Photolysis of Quinolyl and Isoquinolyl Azides in Alcohols Containing Sulfuric Acid

Hiroyuki Sawanishi, Toyoko Hirai, and Takashi Tsuchiya

*School of Pharmacy, Hokuriku University, 3-Ho, Kanagawa machi, Kanazawa 920-1181, Japan


Photolysis of 3-azidoquinoline, 4-azidoisoquinoline, and 4-azidoquinoline N-oxide in alcohols containing sulfuric acid gave the corresponding α-alkoxy amino compounds (2,3,5,7) via nitrenium ion intermediates. In contrast, 3-azidoquinoline N-oxide, 5-azido- and 8-azidoquinoline, and 5-azidoisoquinoline, upon irradiation under similar conditions, gave the different type of α-alkoxy amino compounds such as 9 and 13 via azirine or azacycloheptatetraene intermediates.