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Synthesis of two novel pyridine annulated pyrrolidine nitroxides

Author:

V. C. Jayawardena

Queensland University of Technology, 2 George Street, Brisbane, QLD 4001, AU
About V. C.
ARC Centre of Excellence for Free Radical Chemistry and Biotechnology, Faculty of Science & Engineering
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Abstract

Two novel, unsubstituted, pyridine-annulated pyrrolidine nitroxides; 1,1,3,3-tetramethyl-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-2-yloxyl and 1,1,3,3-tetramethyl-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-5-oxide-2-yloxyl were synthesized in overall yield of ~15% (5 steps starting from pyridine-3,4-dicarboxyic acid) via a Grignard approach. Grignard methylation of N-benzylcinchomeronic imide that was derived from pyridine-3,4-dicarboxylic anhydride, furnished the tetramethylpyrrolidine precursor in an isolated yield of 18%. Hydrogenation of the tetramethyl pyrrolidine precursor followed by oxidation afforded, depending on the oxidation conditions, each of the two nitroxides.

How to Cite: Jayawardena, V. C. (2020). Synthesis of two novel pyridine annulated pyrrolidine nitroxides. Ceylon Journal of Science, 49(3), 253–259. DOI: http://doi.org/10.4038/cjs.v49i3.7776
Published on 25 Sep 2020.
Peer Reviewed

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