Synthesis and Chemistry of Benzo[ e][1,2,6]thiadiazino[3,4- b][1,4]diazepin-10(11 H)-ones and Related Ring Transformations

Andreas S Kalogirou; Andreas Kourtellaris; Panayiotis A Koutentis

doi:10.1021/acs.joc.1c00206

Synthesis and Chemistry of Benzo[ e][1,2,6]thiadiazino[3,4- b][1,4]diazepin-10(11 H)-ones and Related Ring Transformations

J Org Chem. 2021 Apr 16;86(8):5702-5713. doi: 10.1021/acs.joc.1c00206. Epub 2021 Apr 5.

Authors

Andreas S Kalogirou¹, Andreas Kourtellaris², Panayiotis A Koutentis²

Affiliations

¹ Department of Life Sciences, School of Sciences, European University Cyprus, 6 Diogenis Str., Engomi, P.O. Box 22006, 1516 Nicosia, Cyprus.
² Department of Chemistry, University of Cyprus, P.O. Box 20537, 1678 Nicosia, Cyprus.

PMID: 33818096
DOI: 10.1021/acs.joc.1c00206

Abstract

2-[(3,5-Dichloro-4H-1,2,6-thiadiazin-4-ylidene)amino]benzamides are cyclized to benzo[e][1,2,6]thiadiazino[3,4-b][1,4]diazepin-10(11H)-ones via (i) treatment with NaH and via (ii) Pd-catalyzed C-N coupling. The behavior of the latter toward nucleophiles and thermal, oxidative, and reductive conditions revealed unexpected transformations to 3,5-dioxo-4,5-dihydro-3H-benzo[e][1,4]diazepine-2-carbonitrile and 2-(4-substituted-1,2,5-thiadiazol-3-yl)quinazolin-4(3H)-ones.

Publication types

Research Support, Non-U.S. Gov't