20054-73-3Relevant academic research and scientific papers
One - Pot synthesis of novel sulfur and selenium heterocycles by directed ortho-lithiation
Wright
, p. 723 - 726 (2007/10/03)
A procedure for the synthesis of benzo[e][1,3]thiazine-2,4-diones from benzamides by directed lithiation and sequential treatment with sulfur and phosgene is reported. Use of thiophosgene afforded 2-thioxo-2,3-dihydro-benzo[e][1,3]thiazin-4-ones. Application of this methodology to benzenesulfonamides afforded the previously unknown 1,1-dioxo-1,2-dihydro-1,4-dithia-2-aza-naphthalen-3-one ring system with phosgene and the 1,2-dioxo-2-phenyl-2,3-dihydrobenzo[e][1,4,2]dithiazine-3-one ring system with thiophosgene. Use of selenium in place of sulfur afforded the novel analogous selenium heterocycles, however in the case of benzamides the use of selenium and phosgene afforded benzo[d]isoselenazol-3-ones unexpectedly.
