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Paper | Regular issue | Vol 36, No. 3, 1993, pp.519-528
Published online, 1st January, 1970
DOI: 10.3987/COM-92-6202
Selective and Simultaneous Deprotection of Amine and Lactam Functions in the Syntheses of Pyridazino[4,5-b]oxazinones and Pyridazino[4,5-b]thiazinones

Erzsébet Zára-Kaczián and Péter Mátyus*

*Institute for Drug Research Ltd., 47-49 Berlini st.1 H-1045 Budapest, Hungary


Benzyloxymethyl (BOM) and benzyl (Bz) groups were employed for protection of the amide- and amino-nitrogens in the title compounds. The BOM protective group could be removed selectively or simultaneously with the Bz group depending on the reaction conditions. By catalytic hydrogenation of the fully protected pyridazinooxazinone (1b), unexpectedly the 4-methyl derivative (1e) could also be prepared. The mechanism for the formation of 1e is also discussed.