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Communication | Regular issue | Vol 19, No. 6, 1982, pp.1043-1046
Published online, 1st January, 1970
DOI: 10.3987/R-1982-06-1043
Photolysis of Pyridyl, Quinolyl, and Isoquinolyl Azides in Hydrohalogenoic Acids

Hiroyuki Sawanishi, Toyoko Hirai, and Takashi Tsuchiya

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


Photolysis of 4-azido-pyridine and -quinoline in hydrohalogenoic acids gave the 3-amino-4-halogeno compounds (2) via azirine or azacycloheptatetraene intermediates, whereas their N-oxides (4), under similar conditions, gave the 4-amino-3-halogeno compounds (5) presumably via nitrenium ion intermediates. In the 3-azidoquinoline and 4-azidoisoquinoline series, both free bases (6a, 8a) and N-oxides (6b, 8b) gave similar results to 4-azidopyridine and -quinoline N-oxides (4).