Unsymmetrical three-carbon condensations with dimedone

descriptionPublicationkeyboard_double_arrow_right Article 01 Jan 1967 English Publisher:Springer Science and Business Media LLCJournal:Chemistry of Heterocyclic Compounds, volume 2, pages 440-442 (issn: 0009-3122, eissn: 1573-8353,

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Authors: E. I. Stankevich; E. E. Grinshtein; G. Ya. Vanag;

doi: 10.1007/bf00509440

Unsymmetrical three-carbon condensations with dimedone

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Abstract

Condensing together equimolecular amounts of dimedone, an aldehyde, and s-aminocrotonic ester gives derivatives of 3-ethoxycarbonyl-2, 7, 7-trimethyl-5-keto-1, 4, 5, 6, 7, 8-hexahydroquinoline (IVa-c); of these, compounds IVb and IVc can be oxidized by chromic anhydride to 3-ethoxycarbonyl-2, 7, trimethyl-5-keto-5, 6, 7, 8-tetrahydroquinolines (Vb, c). The UV and IR spectra of compounds IVc and Vc are determined. Oxidation splits IVa to bisdimedonylmethane (VI).

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Institute of Organic Synthesis
Russian Federation

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