153705-03-4Relevant articles and documents
3-Hydroxypyrroles and 1H-Pyrrol-3(2H)-ones. Part 13. Reactions of Methoxymethylene Meldrum's Acids with 3-Hydroxypyrroles, with 3-Methoxypyrroles and with other Active Substrates, and Pyrolytic Heterocyclizations of the Products
Derbyshire, Paul A.,Hunter, Gordon A.,McNab, Hamish,Monahan, Lilian C.
, p. 2017 - 2026 (2007/10/02)
Methoxymethylene Meldrum's acid 2 in acetonitrile solution acts a useful C-electrophile for active substrates such as pyrrole, indole or tertiary enaminones to give substitution products (e.g. 5, 6 or 12, respectively).Primary enaminones react exlusively at the nitrogen atom under these conditions.The effect of the ring substituents on the regiochemistry of electrophilic substitution of 3-hydroxypyrroles and 3-methoxypyrroles was studied using methoxymethylene Meldrum's acid as the electrophile.Flash vacuum pyrolysis of the Meldrum's acid derivatives obtained in many of these reactions gave access to a range of heterocyclic systems, including the pyridone 48, quinolinedione 43, benzazepinedione 41 and fused pyrones 50, 52 and 54.