Alkyl 3-nitroacrylates: Synthesis and reactions with cyclohexane-1,3-diones and Meldrum’s acid

V. V. Pelipko; S. V. Makarenko; R. I. Baichurin; V. M. Berestovitskaya; K. S. Kovalenko

doi:10.1134/S107042801712003X

Alkyl 3-nitroacrylates: Synthesis and reactions with cyclohexane-1,3-diones and Meldrum’s acid

Autores: Pelipko V.V.¹, Makarenko S.V.¹, Baichurin R.I.¹, Berestovitskaya V.M.¹, Kovalenko K.S.²
Afiliações:
1. Herzen State Pedagogical University of Russia
2. Chemical and Food Fragrances Factory Ltd.
Edição: Volume 53, Nº 12 (2017)
Páginas: 1799-1808
Seção: Article
URL: https://journal-vniispk.ru/1070-4280/article/view/217014
DOI: https://doi.org/10.1134/S107042801712003X
ID: 217014

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A modified procedure was proposed for the synthesis of alkyl 3-nitroacrylates by nitroiodination of alkyl acrylates and subsequent dehydroiodination of iodonitropropanoates with triethylamine. Alkyl 3-nitroacrylates reacted with cyclohexane-1,3-dione, dimedone, and Meldrum’s acid in the presence of N,N,N-tri-methylanilinium hydroxide (Rodionov’s catalyst) in anhydrous methanol to give the corresponding Michael adducts.