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Abstract
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Five memberd ring lactams have successfully been used in routes to various alkaloides and are suitable precursors for unusual y-amino acids such as statine and its analogues. There are also many examples of pyrroline-containing natural products with pharmacological activities. Typical examples arc the antiturnor alkaloide Jatropham’ and the platelet aggregation inhibitor P1-091. As part of our current studies on the development of new routes to heterocyclic and carbocyclie systems. we report a simple, one-pot, and regioselective synthesis of highly functionalized 5- oxo-2,5-dihydro-1H-pyrroles 3. Thus, reaction of dialkyl acetylenedicarboxylates 1 with N -benzyl- N2-(4-nitrophenyl)-ethanediamide 2 in the presence of triphenyiphosphine leads to dialkyl 4-benzylamino- 1- (4-nitrophenyl)-5-oxo-2,5- dihydro 1 H-pyrrole-2,3-dicarboxylares 3a-3d in good yields.
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