Palladium(0)-catalysed regioselective cyclisations of 2-amino(tosyl) benzamides/sulphonamides: the stereoselective synthesis of 3-ylidene-[1,4]benzodiazepin-5-ones/benzo[f][1,2,5]thiadiazepine-1,1-dioxides

The Pd(0) catalysed cyclisation reactions between tert-butyl propargyl carbonates and 2-aminotosyl benzamides or sulphonamides deliver 1,4-benzodiazepin-5-ones or sultam derivatives, key components of many biologically active compounds. But 2-amino benzamides/sulphonamides require propargyl carbonates substituted at acetylenic carbon to undergo the reaction resulting in the stereoselective formation of the said products.

Automated summary

The cyclisation reactions between tert-butyl propargyl carbonates and 2-aminotosyl benzamides or sulphonamides catalysed by Pd(0) deliver key components of biologically active compounds, 1,4-benzodiazepin-5-ones or sultam derivatives. However, propargyl carbonates substituted at acetylenic carbon are required for the stereoselective formation of the products with 2-amino benzamides/sulphonamides.