223763-38-0Relevant academic research and scientific papers
Heterocyclic synthesis containing bridgehead nitrogen atom: Synthesis of 3-[(2H)- 2-oxobenzo[b]pyran-3-yl]-s-triazolo[3,4-b]-1,3,4-thiadiazine and thiazole derivatives
Raslan
, p. 114 - 120 (2007/10/03)
The reaction of 2H-2-oxobenzo[b]-pyran-3-hydrazide (2) with carbon disulfide in basic DMF afforded potassium thiocarbamate 3, which readily underwent heterocyclization upon its reaction with hydrazine and/or phenacyl bromide to yield 1,2,4-tiazole (4) and thiazole 7 derivatives, respectively. Condensation of 4 with substituted phenacyl bromide and/or chloranil gave 1,2,4-triazole[3,4-b]thiadiazine (5a,b) and 3,10-bis-[2H-2-oxobenzo[b]pyran-3-yl]-6,13-dichloro-bis-[2H-2-oxobenzo[b]pyran-3 -yl]- 6,13-dichloro-bis-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazino [5′,6′-b:5′,6′-e]cyclohexa-1,4-diene (6), respectively. Cyclization of thiosemicarbazide 10 by refluxing it in sodium hydroxide and/or phosphoryl chloride afforded triazole 13 and thiadiazole 15 derivatives, respectively. Also, 10 reacted with phenacyl bromide in the presence of anhydrous sodium acetate to give the oxothiazolidine derivative 17. The structure of the synthesized compounds were confirmed by elemental analyses, IR, 1H NMR, and mass spectra.
