Events The 4th International Electronic Conference on Synthetic Organic Chemistry

Event submissions

Published

This submission belongs to the session a. General Organic Synthesis of the event The 4th International Electronic Conference on Synthetic Organic Chemistry

Published date

11 Sep, 2000

Citation

Pedro M. J. Lory, James N. Iley, Raymond C. F. Jones, An Unexpected Result from a 1,3-Dipolar Cycloaddition: Synthesis of Pyrrolo[1,2,3-de]quinoxalines, in Proceedings of The 4th International Electronic Conference on Synthetic Organic Chemistry, 1 November–30 November 2000, MDPI: Basel, Switzerland, doi: 10.3390/ecsoc-4-01823

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An Unexpected Result from a 1,3-Dipolar Cycloaddition: Synthesis of Pyrrolo[1,2,3-de]quinoxalines

Raymond C. F. Jones ¹

James N. Iley ¹

Pedro M. J. Lory ¹

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

Keywords

n/a

A general, high-yielding synthesis of b-diamides and b-amidoesters

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