摘要/Abstract

报道了一种在四丁基碘化铵(TBAI)和过氧硫酸氢钾复合盐(oxone)存在下, 磺酰自由基诱导N-羟乙基-N-芳基丙炔酰胺的螺-三环化串联反应, 并合成了系列1-芳基-2-对甲苯磺酰基-5,6-二氢苯并[b]吡咯并[2,1-c][1,4]噁嗪-3(7aH)-酮. 螺-三环化串联包括磺酰自由基对炔烃的α-加成、ipso-环化和螺环中间体的邻位俘获.
关键词: 螺-三环化反应, 芳基磺酰化, 自由基, 邻位捕获
A facile procedure is reported for the synthesis of various 1-aryl-2-tosyl-5,6-dihydrobenzo[b]pyrrolo[2,1-c][1,4]- oxazin-3(7aH)-one via a radical arylsulfonylation-induced ipso-cyclization-ortho-cyclization sequence of N-hydroxylethyl-N- arylpropiolamides in the presence of tetra-n-butylammonium iodide (TBAI) and oxone. The radical cyclization sequence involves a sulfonyl radical α-addition into the alkyne, ipso-cyclization, and ortho-trapping of the spirocyclic intermediate.
Key words: spiro-tricyclization, arylsulfonylation, radical, ortho-capture


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