Reaction of arylisocyanates 2 with methyl 2-oxo-2H-pyran-6-acetate 1 and with ylide 4 gave two classes of pyronylacetamides 3 and 5, respectively. Phosphoranes 5 were reduced to the corresponding acetamides 6 with zinc and acetic acid. Compounds 6 were alkylated under solid-liquid PTC conditions using anhydrous potassium carbonate as a base to give the Cα-alkyl derivatives 7 in good yields. Intramolecular cyclization with different bases and solvents of acetamides 3,5-7 to give the new 2,5,7-trioxo-pyrano[3,2-c]pyridines has been studied.
α-Pyrones. Part V. Structure effects on the intramolecular cyclization of functionalized 6-pyronylacetamides: synthesis of new 2,5,7-trioxo-pyrano[3,2-c]pyridines / F. Clerici, M.L. Gelmi, B. Galbiati, S. Mottadelli, M. Penso, D. Pocar. - In: TETRAHEDRON. - ISSN 0040-4020. - 51:11(1995), pp. 3279-3288.
α-Pyrones. Part V. Structure effects on the intramolecular cyclization of functionalized 6-pyronylacetamides: synthesis of new 2,5,7-trioxo-pyrano[3,2-c]pyridines
F. ClericiPrimo
;M.L. GelmiSecondo
;D. PocarUltimo
1995
Abstract
Reaction of arylisocyanates 2 with methyl 2-oxo-2H-pyran-6-acetate 1 and with ylide 4 gave two classes of pyronylacetamides 3 and 5, respectively. Phosphoranes 5 were reduced to the corresponding acetamides 6 with zinc and acetic acid. Compounds 6 were alkylated under solid-liquid PTC conditions using anhydrous potassium carbonate as a base to give the Cα-alkyl derivatives 7 in good yields. Intramolecular cyclization with different bases and solvents of acetamides 3,5-7 to give the new 2,5,7-trioxo-pyrano[3,2-c]pyridines has been studied.Pubblicazioni consigliate
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