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Nitrogen bridgehead compounds. Part 60. Unusual amination with sodium azide.
Authors:István Bitter  Gábor Tóth  Áron Szöllősy  István Hermecz  Zoltán Mészáros
Affiliation:1. Technical University, Department of Organic Chemistry and Technology, H-1111 Budapest, Hungary;2. NMR Laboratory of the Institute of General and Analytical Chemistry, H-1111 Budapest, Hungary;3. CHINOIN Pharm. and Chem. Works, H-1325 Budapest, P.O. Box 110, Hungary.
Abstract:9-Bromo-6,7,8,9-tetrahydro-4H-pyrido [1,2-a]pyrimidin-4-ones react with sodium azide to afford 9-amino-6,7-dihydroanalogues. A mechanism involving a tricyclic tetrazine intermediate formed by neighbouring-group participation is suggested.
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