Journal of the Chemical Society. Perkin transactions I p. 419 - 424 (1989)
Update date:2022-08-04
Topics:
McNab, Hamish
Monahan, Lilian C.
Reaction of the pyrrolone (2) with N-, C-, and halogen-electrophiles takes place at the 4-position to give the azo compounds (3)-(5), the 'methylene Meldrum's' derivative (12) and the halogeno derivatives (16)-(18).Reductive cleavage of the azo compound (5) gives a convenient route to the 4-aminopyrrolone (7), which may be diazotized and coupled with 2-naphthol.Decomposition of the Meldrum's derivative (12) with base leads to the malonates (13) and (14) and acrylate (15).Deuterium exchange at the 5-position takes place when the halogeno compounds (16)-(18) are treated with <2H3>methoxide in <2H4>methanol: the 5-anion is thought to be an intermediate.Protodehalogenation of the 4-bromo- and 4-iodo-derivatives (17) and (18) occurs on treatment with triphenylphosphine.
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