Journal of the Chemical Society. Perkin transactions I p. 2017 - 2026 (1993)
Update date:2022-09-26
Topics:
Derbyshire, Paul A.
Hunter, Gordon A.
McNab, Hamish
Monahan, Lilian C.
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.
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