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An Unexpected Result from a 1,3-Dipolar Cycloaddition: Synthesis of Pyrrolo[1,2,3-de]quinoxalines
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1  Chemistry Department, Loughborough University, Loughborough, Leics. LE11 3TU, UK

Abstract: As part of a programme to evaluate the imidazolinium ylides 2 in 1,3-dipolar cycloaddition reactions [1], we wished to explore intramolecular cycloaddition. The azomethine ylides 2 are prepared (Scheme 1) by alkylation of imidazolines 1 with an active halide such as an a-halo ester (X = CO2R) and addition of a base (DBU); in the presence of a dipolarophile, the dipole 2 undergoes regioselective and diasteroselective cycloaddition (e.g. Scheme 1). Thus in onepot, three of the five bonds of a new pyrrolidine ring are assembled
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