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.
|Titolo:||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|
CLERICI, FRANCESCA (Primo)
GELMI, MARIA LUISA (Secondo)
POCAR, DONATO (Ultimo)
|Settore Scientifico Disciplinare:||Settore CHIM/06 - Chimica Organica|
|Data di pubblicazione:||1995|
|Digital Object Identifier (DOI):||http://dx.doi.org/10.1016/0040-4020(95)00050-I|
|Appare nelle tipologie:||01 - Articolo su periodico|