The first divergent cyclization reactions of benzo[c][1,2]dithiol-3-ones to assemble six- and eight-membered N-containing heterocycles is displayed herein. This unprecedented formal [4+4]/[4+2] cycloadditions of 3H-benzo[c][1,2]dithiol-3-ones and hexahydro-1,3,5-triazines was controlled by the N-substituent group of hexahydro-1,3,5-triazines. This newly discovered tactic features as transition-metal-free, no inert gas protection, easily to operate, mild conditions, decent yields, broad substrate scope and accessible scalability.

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