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Synthesis of Tetracyclic 2,3-Dihydro-1,3-diazepines from a Dinitrodibenzothiophene derivative

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journal contribution
posted on 2018-10-09, 08:00 authored by Stephanie Montanaro, Iain Wright, Andrei S. Batsanov, Martin R. Bryce
Triply fused 1,3-diazepine derivatives have been obtained by acidic reduction of rotationally locked and sterically hindered nitro groups in the presence of an aldehyde or ketone. The nitro groups are sited on adjacent rings of a dicyanodibenzothiophene-5,5-dioxide, which also displays fully reversible two-electron-accepting behavior. The synthesis, crystallographically determined molecular structures, and aspects of the electronic properties of these new molecules are presented.

Funding

M.R.B. and I.A.W. thank EPRSC for funding (EP/K016164/1). I.A.W. thanks Loughborough University and the Royal Society of Chemistry Research Fund (RF18-5353) for funding.

History

School

  • Science

Department

  • Chemistry

Citation

MONTANARO, S. ... et al., 2018. Synthesis of Tetracyclic 2,3-Dihydro-1,3-diazepines from a Dinitrodibenzothiophene derivative. Journal of Organic Chemistry, 83(19), pp. 12320–12326.

Publisher

© American Chemical Society

Version

  • AM (Accepted Manuscript)

Publisher statement

This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of Organic Chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://pubs.acs.org/doi/10.1021/acs.joc.8b02029.

Publication date

2018-09-24

ISSN

0022-3263

eISSN

1520-6904

Language

  • en

Location

United States

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