Visible-light-induced metal-free cascade cyclization of N-arylpropiolamides to 3-phosphorylated, trifluoromethylated and thiocyanated azaspiro[4.5]trienones,Organic Chemistry Frontiers

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Visible-light-induced metal-free cascade cyclization of N-arylpropiolamides to 3-phosphorylated, trifluoromethylated and thiocyanated azaspiro[4.5]trienones
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2020-12-21 , DOI: 10.1039/d0qo01410a
Fan-Lin Zeng _{1,

2,

3,

4,

5} , Xiao-Lan Chen _{1,

2,

3,

4,

5} , Kai Sun _{1,

2,

3,

4,

5} , Hu-Lin Zhu _{1,

2,

3,

4,

5} , Xiao-Ya Yuan _{1,

2,

3,

4,

5} , Yan Liu _{1,

2,

3,

4,

5} , Ling-Bo Qu _{1,

2,

3,

4,

5} , Yu-Fen Zhao _{1,

2,

3,

4,

5} , Bing Yu _{1,

2,

3,

4,

5}

Affiliation

Photocatalytic strategies for the preparation of 3-phosphoryl/trifluoromethyl/thiocyanato azaspiro[4.5]trienones via a radical-initiated cascade annulation reaction of N-arylpropiolamides with phosphorus reagents, 1-trifluoromethyl-1,2-benziodoxol-3(1H)-one (Togni's reagent II) or NH₄SCN have been developed under blue LED irradiation at room temperature. The novel synthetic methodologies constitute the first application of 2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile (4CzIPN) as a photocatalyst for the synthesis of spiro-γ-lactam derivatives, in which the use of transition metals and a high reaction temperature could be avoided. The reactions are operationally simple, easy to scale up, and metal-free with wide reaction scope and good functional group tolerance.

中文翻译：

N-芳基丙酰胺的可见光诱导的无金属级联环化成3-磷酸化，三氟甲基化和硫氰酸化的氮杂螺并[4.5]三烯酮

通过自由基引发的N-芳基丙酰胺与磷试剂1-三氟甲基-1,2-苯并恶多酚-3（1 H）-的级联环化反应制备3-磷酰基/三氟甲基/硫氰酸根氮杂螺并[4.5]三烯酮的光催化策略在室温下在蓝色LED照射下已经开发出一种（Togni试剂II）或NH ₄ SCN。新颖的合成方法构成了2,4,5,6-tetra（9 H-咔唑-9-基）间苯二甲腈（4CzIPN）作为合成螺-γ-内酰胺衍生物的光催化剂，可避免使用过渡金属和高反应温度。反应操作简单，易于规模化，并且不含金属，反应范围广，官能团耐受性好。

更新日期：2021-01-05

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