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

Montanaro, Stephanie; Wright, Iain A.; Batsanov, Andrei S.; Bryce, Martin R.

doi:10.1021/acs.joc.8b02029

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

Montanaro, Stephanie; Wright, Iain A.; Batsanov, Andrei S.; Bryce, Martin R.

Authors

Stephanie Montanaro

Iain A. Wright

Dr Andrei Batsanov a.s.batsanov@durham.ac.uk
Academic Visitor

Professor Martin Bryce m.r.bryce@durham.ac.uk
Professor

Abstract

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.

Citation

Montanaro, S., Wright, I. A., Batsanov, A. S., & Bryce, M. R. (2018). Synthesis of Tetracyclic 2,3-Dihydro-1,3-diazepines from a Dinitrodibenzothiophene Derivative. Journal of Organic Chemistry, 83(19), 12320-12326. https://doi.org/10.1021/acs.joc.8b02029

Journal Article Type	Article
Online Publication Date	Sep 24, 2018
Publication Date	Oct 5, 2018
Deposit Date	Sep 26, 2018
Publicly Available Date	Sep 24, 2019
Journal	Journal of Organic Chemistry
Print ISSN	0022-3263
Electronic ISSN	1520-6904
Publisher	American Chemical Society
Peer Reviewed	Peer Reviewed
Volume	83
Issue	19
Pages	12320-12326
DOI	https://doi.org/10.1021/acs.joc.8b02029
Public URL	https://durham-repository.worktribe.com/output/1317968

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Copyright 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://doi.org/10.1021/acs.joc.8b02029.