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Photolysis of 1,6-naphthyridine 1,6-dioxide and its theoretical consideration

✍ Scribed by Yoshiro Kobayashi; Itsumaro Kumadaki; Haruo Sato


Book ID
104249049
Publisher
Elsevier Science
Year
1970
Tongue
French
Weight
183 KB
Volume
11
Category
Article
ISSN
0040-4039

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✦ Synopsis


oxide type and the other is of isoquinoline Z-oxide type.

It was, therefore, attractive to examine which N-oxide group would be isomerized faster in the photolysis.

Photolysis of I in water by a high-pressure mercury lamp with a Pyrex filter afforded 1,2-dihydro-1,6-naphthyridin-Z(lH)one 6-oxide (III), mp 325' (decomp).

This experiment suggested I has photo-selectivity in a protic solvent and that the photomigration of l-oxide is faster than that of 6-oxide. Irradia-


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A regioselective alkylation of naphthyridines 4a-d, through the action of ethylchloroformate and benzylstannane 5, afforded the benzyl substituted dihydronaphthyridines 3a-d. These key intermediates 3a-d were transformed into the desired targets 2a-d in seven steps.