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Synthesis of bicyclic tetrahydropyridine enamides and enecarbamates by hetero-Cope rearrangement of nitroso cycloadducts

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Chemistry of Heterocyclic Compounds Aims and scope

The hetero-Cope rearrangement reactions of inverse carbamate and amide nitroso Diels–Alder cycloadducts with 1,2-dihydropyridines to give novel tetrahydropyridine enamides and enecarbamates have been studied in detail identifying optimal reaction conditions. The possibility to obtain tetrahydropyridine enamides and carbamates containing a free OH at the C-4 position is restricted to only particular substitution patterns when dealing with carbamate nitroso cycloadducts. On the other hand, starting from easily available amide nitroso cycloadducts and catalytic amounts of cuprous salts, it is now possible to obtain several substituted 4a,7,8a-tetrahydropyrido[4,3-e]-[1,4,2]dioxazines in moderate to good yields.

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Notes

  1. Here and below in Experimental, one asterisk (*) denotes a signal of minor rotamer.

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We gratefully acknowledge the financial support from P.R.A. 2016_27 by the University of Pisa.

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Authors and Affiliations

  1. Dipartimento di Farmacia, Sede di Chimica Bioorganica e Biofarmacia, Università di Pisa, 33 Via Bonanno, 56126, Pisa, Italy

    Francesco Berti, Andrea Menichetti, Valeria Di Bussolo, Lucilla Favero & Mauro Pineschi

  2. Dipartimento di Chimica e Chimica Industriale, Università di Pisa, 3 Via G. Moruzzi, 56124, Pisa, Italy

    Valeria Di Bussolo

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  1. Francesco Berti
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  2. Andrea Menichetti
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  3. Valeria Di Bussolo
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  4. Lucilla Favero
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  5. Mauro Pineschi
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Correspondence to Mauro Pineschi.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2018, 54(4), 458–468

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Berti, F., Menichetti, A., Di Bussolo, V. et al. Synthesis of bicyclic tetrahydropyridine enamides and enecarbamates by hetero-Cope rearrangement of nitroso cycloadducts. Chem Heterocycl Comp 54, 458–468 (2018). https://doi.org/10.1007/s10593-018-2289-8

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