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

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

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


Authors

Stephanie Montanaro

Iain A. Wright



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

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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.





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