The synthesis of methyl 2-(benzyloxycarbonyl)amino-3-dimethylaminopropenoate. The synthesis of trisubstituted pyrroles, 3-amino-2H-pyran-2-ones, fused 2H-pyran-2-ones and 4H-pyridin-4-ones

✍ Scribed by Renata Toplak; Jurij Svete; Branko Stanovnik; Simona GoliČ Grdadolnik

• Publisher: Journal of Heterocyclic Chemistry
• Year: 1999
• Tongue: English
• Weight: 636 KB
• Volume: 36
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570360135

✦ Synopsis

Methyl 2-(benzyloxycarbonyl)amino-3-dimethylaminopropenoate (2) was prepared from methyl (\mathrm{N})-(benzyloxycarbonyl)glycinate (1) and (t)-butoxybis(dimethylamino)methane, and used as a reagent for preparation of substituted 3-(benzyloxycarbonyl)amino-4 (\mathrm{H})-quinolizin-4-ones 5 and (6,-2 \mathrm{H})-pyran-2-ones 17-19, -2H-1benzopyran-2-ones 28-31, and -naphthopyrans 32-35, -2H-pyrano[3,2-c]pyridine-2,5-dione 46, -pyrano[4,3-b]pyran-2,5-dione 47, -pyrano[3,2-c]benzopyran-2,5-dione 48, -pyrano[2,3-c]pyrazol-6-ones 49 and 50, -pyrano[2,3-d] pyrimidin-7-ones 51 and 52 derivatives. In the reaction of (\mathbf{2}) with 1,3-diketones trisubstituted pyrroles 14-16 were formed. Selective removal of benzyloxycarbonyl group was achieved by catalytic transfer hydrogenation with (\mathrm{Pd} / \mathrm{C}) in the presence of cyclohexene to afford free 3-amino compounds (7,8,20,36-38) and (53-57) in yields better than (80 %).