Cyclic nitrones. I. Reactions of α-keto nitrones at nitrone carbon

descriptionPublicationkeyboard_double_arrow_right Article 01 Feb 1967 English Publisher:CSIRO PublishingJournal:Australian Journal of Chemistry, volume 20, pages 339-347 (issn: 0004-9425, eissn: 1445-0038,

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Authors: RFC Brown; L Subrahmanyan; CP Whittle;

doi: 10.1071/ch9670339

Cyclic nitrones. I. Reactions of α-keto nitrones at nitrone carbon

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Abstract

The chemistry of 3,4,5,6-tetrahydro-3-oxopyridine 1-oxides has been studied with respect to: reaction with hydrazine-the 6,6-dimethyl compound (IV) gave a hydrazone (VII) by ring contraction following initial attack at C 2; (ii)(ii) 2-arylation with diazonium salts, e.g. conversion of (III) into (XIII); (iii) acid- and base-catalysed deuterium exchange at C 2, C 4, and C 6; (iv)(iv) oxidation of the 5,5-dimethyl compound (III) by chromate ion to a 2,2?-linked dimer (XV).

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