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Intramolecular [4+2] cycloaddition in N-allyl- and N-propargyl-α-furyl lactams

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Chemistry of Heterocyclic Compounds Aims and scope

The size of nitrogen heterocycle in N-allyl- and N-propargyl-α-furyl lactams, as well as the nature of the unsaturated substituent linked to the nitrogen atom affected the possibility of thermal intramolecular [4+2] cycloaddition between multiple bond and the furan ring. N-Allyl-γ-(α-furyl)butyrolactam was shown to be unreactive at temperatures from 140 to 230°С. Substituted δ-valero- and ε-caprolactams underwent partial Diels–Alder cyclization, forming tautomeric mixtures that contained both the initial open-chain form and the cyclic form (diastereomeric 3a,6-epoxyisoindoles fused with an aza ring) in ratios between 19:81 and 55:45. N-Propargyl-α-furyl lactams did not participate in thermal IMDAF reaction regardless of the ring size and the temperature of the synthesis.

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Synthesis of the starting compounds 2 and 3 was supported by the Russian Foundation for Basic Research (grant No. 17-53-45016). The synthesis and NMR spectroscopy of adducts 4 were performed with financial support from the RUDN University program ''5-100''.

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Authors and Affiliations

  1. RUDN University, 6 Miklukho-Maklaya St., Moscow, 117198, Russia

    Dmitry S. Poplevin, Eugeniya V. Nikitina, Vladimir P. Zaytsev, Alexey V. Varlamov & Fedor I. Zubkov

  2. Goa University, Taleigao Plateau, Goa, 403206, India

    Santosh G. Tilve

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  1. Dmitry S. Poplevin
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  2. Eugeniya V. Nikitina
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  3. Vladimir P. Zaytsev
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  4. Alexey V. Varlamov
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  5. Santosh G. Tilve
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  6. Fedor I. Zubkov
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Correspondence to Fedor I. Zubkov.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2018, 54(4), 451–457

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Poplevin, D.S., Nikitina, E.V., Zaytsev, V.P. et al. Intramolecular [4+2] cycloaddition in N-allyl- and N-propargyl-α-furyl lactams. Chem Heterocycl Comp 54, 451–457 (2018). https://doi.org/10.1007/s10593-018-2290-2

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  • DOI: https://doi.org/10.1007/s10593-018-2290-2

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