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Photochemical synthesis of 6-substituted 12-oxo-6,12-dihydroazepino[2,1-b]quinazolines

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Chemistry of Heterocyclic Compounds Aims and scope

A method for the synthesis of 6-substituted 12-oxo-6,12-dihydroazepino[2,1-b]quinazolines via a photoinitiated reaction of orthosubstituted aryl azides with sodium 2-aminobenzoate is proposed. Stepwise annulation of the quinazoline system to the azepine ring occurs during nucleophilic addition of an amine to a cyclic keteneimine generated by photolysis of an aryl azide and subsequent intramolecular condensation of the intermediate product.

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Authors and Affiliations

  1. Lobachevsky State University of Nizhny Novgorod, 23/5 Gagarina Ave., Nizhny Novgorod, 603950, Russia

    Andrei V. Budruev & Daria Yu. Dzhons

  2. Chemistry Research Institute of Lobachevsky State University of Nizhny Novgorod, 23/5 Gagarina Ave., Nizhny Novgorod, 603950, Russia

    Vladimir I. Faerman

  3. G. A. Razuvaev Institute of Organometallic Chemistry of Russian Academy of Sciences, 49 Tropinina St., Nizhny Novgorod, 603950, Russia

    Georgy K. Fukin & Andrey S. Shavyrin

Authors
  1. Andrei V. Budruev
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  2. Daria Yu. Dzhons
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  3. Vladimir I. Faerman
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  4. Georgy K. Fukin
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  5. Andrey S. Shavyrin
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Correspondence to Andrei V. Budruev.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2016, 52(9), 694–699

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Budruev, A.V., Dzhons, D.Y., Faerman, V.I. et al. Photochemical synthesis of 6-substituted 12-oxo-6,12-dihydroazepino[2,1-b]quinazolines. Chem Heterocycl Comp 52, 694–699 (2016). https://doi.org/10.1007/s10593-016-1951-2

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  • DOI: https://doi.org/10.1007/s10593-016-1951-2

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