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Alkyl 3-bromo-3-nitroacrylates – convenient building blocks for the construction of benzo-fused six-membered N,N-, N,O- and five-membered O,O-heterocycles

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Chemistry of Heterocyclic Compounds Aims and scope

The reactions of alkyl 3-bromo-3-nitroacrylates with N,N-, N,O-, and О,О-o-phenylene bisnucleophiles resulted in the formation of benzo-fused heterocycles: reactions with о-phenylenediamines and о-aminophenols gave six-membered N,N- and N,O-heterocycles – (Z)-3-nitromethylidene-3,4-dihydroquinoxalin-2(1Н)-ones and (Z)-3-nitromethylidene-3,4-dihydro-2Н-1,4-benzoxazin-2-ones, while the use of pyrocatechols led to the formation of a five-membered O,O-heterocyclic system, providing alkyl 2-(nitromethyl)-1,3-benzodioxole-2-carboxylates. The nitroenamine moiety of the obtained six-membered heterocycles was shown to undergo tautomeric transformations.

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The physicochemical studies were performed on the equipment of Collective Use Center at the Faculty of Chemistry, Herzen State Pedagogical University of Russia.

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Authors and Affiliations

  1. Herzen State Pedagogical University of Russia, 48 Moyka River Embankment, Saint Petersburg, 191186, Russia

    Sergey V. Makarenko, Kirill D. Sadykov & Ruslan I. Baichurin

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  1. Sergey V. Makarenko
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  2. Kirill D. Sadykov
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  3. Ruslan I. Baichurin
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Correspondence to Sergey V. Makarenko.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2018, 54(5), 502–507

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Makarenko, S.V., Sadykov, K.D. & Baichurin, R.I. Alkyl 3-bromo-3-nitroacrylates – convenient building blocks for the construction of benzo-fused six-membered N,N-, N,O- and five-membered O,O-heterocycles. Chem Heterocycl Comp 54, 502–507 (2018). https://doi.org/10.1007/s10593-018-2296-9

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