钯催化氰醇吲哚一锅法合成吲哚氮杂环酮及性质

Palladium-catalyzed Synthesis of Indole Azacyclones From Cyanohydrins and Indoles by One-pot Method and Its Properties

探讨钯活化分子内氰醇吲哚碳(C_(sp2))氢键对氰基(—CN)的加成环化反应,一步合成吲哚咔唑类化合物的可行性。用C_(3)、C_(2)、N_(1)吲哚位氰醇作原料对氰基的加成环化反应,经Pd活化分子内C—H键在温和(120℃)回流(24 h)的反应条件下,一锅法合成了14个吲哚衍生物(如四氢咔唑、吡啶吲哚、吲哚咔唑、2-氨基咔唑以及5-氨基咔唑),产率达67%~98%。所有产物用熔点、^(1)H NMR、^(13)C NMR、MS和IR等仪器进行了结构表征,用福井函数及信息熵关联了24个衍生物的亲电(核)活性与药物半致死量(LD50)之间的函数关系,找到了2个相关性好的(R^(2)=0.8~0.9)线性方程式。

The feasibility of one-pot synthesis of indole carbazole compounds by palladium-catalyzed addition cyclization of cyano group(—CN)by intramolecular cyanohydrin indole hydrocarbon bond(C_(sp2))was investigated.A series of functionalized[1,2-a]indole,tetrahydrocarbazole and indolo-7,8-membered carbazole compounds and 2,3,4-tetrahydro-carbazole were synthesized by palladium-catalyzed cycloaddition of cyano groups to indole at C_(3),C_(2),N_(1) sites under mild reflux conditions.Fourteen compounds were synthesized with yields of 67%~98%.All the products were characterized by melting point,^(1)H NMR,^(13)C NMR,MS and IR.Finally,the active sites of reactants were predicted by Fukui function with Materials Studio 8.0 packs and Gaussion 09 W.Two linear equations with good correlation were found.