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  • Copper-catalyzed cascade syntheses of 2H-benzo[b][1,4]thiazin-3(4H)-ones and quinoxalin-2(1H)-ones through capturing S and N atom respectively from AcSH and TsNH(2).

Copper-catalyzed cascade syntheses of 2H-benzo[b][1,4]thiazin-3(4H)-ones and quinoxalin-2(1H)-ones through capturing S and N atom respectively from AcSH and TsNH(2).

The Journal of organic chemistry (2010-07-30)
Dingben Chen, Zhi-Jing Wang, Weiliang Bao
ABSTRACT

A copper-catalyzed cascade method has been developed to synthesize the 2H-benzo[b][1,4]thiazin-3(4H)-ones from 2-halo-N-(2-halophenyl)-acetamides 1 and AcSH via the S(N)2/deacetylation/coupling process, and to synthesize the quinoxalin-2(1H)-ones from 1 and TsNH(2) via the S(N)2/coupling/desulfonation process. The target products were obtained with diversity at three positions on their scaffolds.

MATERIALS
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Sigma-Aldrich
p-Toluenesulfonamide, ReagentPlus®, ≥99%
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Sigma-Aldrich
p-Toluenesulfonamide, reagent grade, 97%
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Availability
Price
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