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Acid-mediated cyclotransformations of 4a-substituted 4H-4a,5-dihydroindeno[1,2-b]pyridines as a new route to 9a-substituted 1H-fluorenes

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

4a-Substituted dihydroindenopyridines undergo cleavage of the C(9b)=N bond in water-containing acidic medium, resulting in the formation of diastereomeric ethyl α-acetyl-β-(2,3-dihydro-1,3-dioxo-1H-inden-2-yl)-β-phenylpropionates and 9a-substituted 1,9a-dihydrofluore-none derivatives. The cyclization of α-acetyl-β-(2,3-dihydro-1,3-dioxo-1H-inden-2-yl)-β-phenyl-propionates with benzylammonium acetate affords 3-benzylamino-1,9a-dihydrofluorenones. The methanobenzo[a]azulene compound is also found among cyclization products.

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Authors and Affiliations

  1. Latvian Institute of Organic Synthesis, Riga, LV-1006, Latvia

    S. Stupnikova, Dz. Muceniece & V. Lūsis

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  1. S. Stupnikova
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  2. Dz. Muceniece
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  3. V. Lūsis
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Translated from Khimiya Geterotsiklicheskikh Soedinenii. No. 2, pp. 249–258, February, 2007.

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Stupnikova, S., Muceniece, D. & Lūsis, V. Acid-mediated cyclotransformations of 4a-substituted 4H-4a,5-dihydroindeno[1,2-b]pyridines as a new route to 9a-substituted 1H-fluorenes. Chem Heterocycl Compd 43, 197–206 (2007). https://doi.org/10.1007/s10593-007-0032-y

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  • DOI: https://doi.org/10.1007/s10593-007-0032-y

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