2-[(3,5-Dichloro-4-1,2,6-thiadiazin-4-ylidene)amino]benzamides are cyclized to benzo[][1,2,6]thiadiazino[3,4-][1,4]diazepin-10(11)-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-3-benzo[][1,4]diazepine-2-carbonitrile and 2-(4-substituted-1,2,5-thiadiazol-3-yl)quinazolin-4(3)-ones.
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