3-Hydroxypyrroles and 1H-pyrrol-3(2H)-ones. Part 13. Reactions of methoxymethylene Meldrum's acid with 3-hydroxypyrroles, with 3-methoxypyrroles and with other active substrates, and pyrolytic heterocyclisations of the products

Abstract

Methoxymethylene Meldrum's acid 2 in acetonitrile solution acts as 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 exclusively at the nitrogen atom under these conditions. The effect of 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, 52and 54.