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Synthesis, crystal structure, and photophysical properties of dimethyl 7-oxa-2a1-azabenzo[b]cyclopenta[pq]pleiadene-1,2-dicarboxylate – novel fused oxazapolycyclic skeleton

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Chemistry of Heterocyclic Compounds Aims and scope

Dimethyl 3-(2-bromophenyl)dibenzo[b,f]pyrrolo[1,2-d][1, 4]oxazepine-1,2-dicarboxylate and its 3,13b-dihydro and 1,2,3,13b-tetrahydro analogs undergo intramolecular cyclization under free radical conditions with the formation of dimethyl 7-oxa-2a1-azabenzo[b]-cyclopenta[pq]pleiadene-1,2-dicarboxylate, the unique representative of pyrrole-fused dibenzo[b,f][1, 4]oxazepines, consisting of six fused rings. This nonplanar oxazapolyheterocycle shows a strong blue emission in dichloromethane.

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We gratefully acknowledge the financial support of the Russian Science Foundation (grant No. 16-13-10036). This research was carried out using resources of the Center for Magnetic Resonance, the Computer Center, and the Center for Chemical Analysis and Materials, the Center for Optical and Laser Materials Research of Saint Petersburg State University.

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Authors and Affiliations

  1. Institute of Chemistry, Saint Petersburg State University, 7/9 Universitetskaya Embankment, Saint Petersburg, 199034, Russia

    Petr P. Petrovskii, Olesya A. Tomashenko, Mikhail S. Novikov & Alexander F. Khlebnikov

  2. Institute of Physics, University of Neuchâtel, rue Emile-Argand 11, CH-2000, Neuchâtel, Switzerland

    Helen Stoeckli-Evans

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  1. Petr P. Petrovskii
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  2. Olesya A. Tomashenko
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  3. Mikhail S. Novikov
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  4. Alexander F. Khlebnikov
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  5. Helen Stoeckli-Evans
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Correspondence to Alexander F. Khlebnikov.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(8), 909–912

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Petrovskii, P.P., Tomashenko, O.A., Novikov, M.S. et al. Synthesis, crystal structure, and photophysical properties of dimethyl 7-oxa-2a1-azabenzo[b]cyclopenta[pq]pleiadene-1,2-dicarboxylate – novel fused oxazapolycyclic skeleton. Chem Heterocycl Comp 53, 909–912 (2017). https://doi.org/10.1007/s10593-017-2144-3

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  • DOI: https://doi.org/10.1007/s10593-017-2144-3

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