SYNTHESIS, CRYSTAL STRUCTURE, AND PHOTOPHYSICAL PROPERTIES OF DIMETHYL 7-OXA-2a<sup>1</sup>-AZABENZO[<i>b</i>]CYCLOPENTA[<i>pq</i>]PLEIADENE- 1,2-DICARBOXYLATE – NOVEL FUSED OXAZAPOLYCYCLIC SKELETON

Authors

  • Petr P. Petrovskii Institute of Chemistry, Saint Petersburg State University, 7/9 Universitetskaya Embankment, Saint Petersburg 199034
  • Olesya A. Tomashenko Institute of Chemistry, Saint Petersburg State University, 7/9 Universitetskaya Embankment, Saint Petersburg 199034
  • Mikhail S. Novikov Institute of Chemistry, Saint Petersburg State University, 7/9 Universitetskaya Embankment, Saint Petersburg 199034
  • Alexander F. Khlebnikov Institute of Chemistry, Saint Petersburg State University, 7/9 Universitetskaya Embankment, Saint Petersburg 199034
  • Helen Stoeckli-Evans Institute of Physics, University of Neuchâtel, rue Emile-Argand 11, Neuchâtel CH-2000

DOI:

https://doi.org/10.1007/4212

Keywords:

oxazaheterocycle, crystal structure, fluorescence, radical arylation

Abstract

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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Published

2017-10-04

Issue

Vol. 53 No. 8 (2017)

Section

Original Papers