A Ring Expansion Route to Benzofused N-Heterocycles Through Aryne Insertion into 1,3-Diaza-heterocycles
A Ring Expansion Route to Benzofused N-Heterocycles Through Aryne Insertion into 1,3-Diaza-heterocycles
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DOI：
10.1002/ejoc.201900570
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发表时间：
2019-09
影响因子：
2.8
通讯作者：
Yun-Chin Yang;Yue Xu;C. Jones
中科院分区：
文献类型：
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作者：
Yun-Chin Yang;Yue Xu;C. Jones
第一次发现了芳炔在C（sp3）-N键中进行了形式的σ键插入。该转化用于1，3-二氮杂-杂环的扩环，以在单个步骤中得到苯并稠合的中环N-杂环。这代表了直接从容易获得的咪唑烷制备生物相关的2，3，4，5-四氢-1H-苯并[e][1，4]二氮杂卓的新途径。还报道了1，3-二氮杂环丁烷的扩环的实例，其提供相应的1，2，3，4-四氢喹唑啉。
Arynes have been found to undergo formal σ‐bond insertion into a C(sp3)–N bond for the first time. This transformation is utilized in the ring expansion of 1,3‐diaza‐heterocycles to afford benzofused medium‐ring N‐heterocycles in a single step. This represents a novel route to biologically relevant 2,3,4,5‐tetrahydro‐1H‐benzo[e][1,4]diazepines, prepared directly from easily accessible imidazolidines. An example of the ring expansion of a 1,3‐diazetidine is also reported, which affords the corresponding 1,2,3,4‐tetrahydroquinazoline.