Hd. Stachel et J. Schachtner, SYNTHESIS OF HETERO ANALOGS OF PENICILLIC ACID, Zeitschrift fur Naturforschung. B, A journal of chemical sciences, 51(9), 1996, pp. 1334-1338
Grignard reaction of maleic acid imides 2a and c with isopropenyl magn
esium bromide gives rise to 3a and, after deprotection, 4c, shown to b
e true analogues of penicillic acid 1. Contrastingly, the correspondin
g N-amino-imide 2b and the thioanhydride 2d react via ring enlargement
to afford the pyridazinone 3b and the thiepindione 3d, respectively.