[4 + 2] Annulation Reaction of In Situ Generated Azoalkenes with Azlactones: Access to 4,5-Dihydropyridazin-3(2H)-Ones
[4 + 2] Annulation Reaction of In Situ Generated Azoalkenes with Azlactones: Access to 4,5-Dihydropyridazin-3(2H)-Ones
复制标题
[4 2] 原位生成的偶氮烯烃与二氢唑酮的成环反应：获得 4,5-二氢哒嗪-3(2H)-Ones
DOI：
10.1021/acs.joc.0c01592
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发表时间：
2020
影响因子：
3.6
通讯作者：
Ming-Qiang Zhou
中科院分区：
文献类型：
--
作者：
Wei-Cheng Yuan;Bao-Xue Quan;Jian-Qiang Zhao;Yong You;Zhen-Hua Wang;Ming-Qiang Zhou
本文报道了一种新颖的偶氮烯烃与吖内酯的[4 + 2]成环反应。该反应提供了一种简便的获得4，5-二氢哒嗪-3（2 H）-酮衍生物的方法，这些衍生物作为潜在的生物活性候选物在医学应用中非常有前途。值得注意的是，这些二氢哒嗪酮也可以通过由N-酰基氨基酸原位生成的氮杂内酯和由α-卤代腙原位生成的偶氮烯烃通过一锅反应方案合成。该方法的潜在应用也通过克级实验和产物转化为其他含氮化合物的多功能转化来证明。
An unprecedented [4 + 2] annulation reaction betweenin situformed azoalkenes and azlactones has been developed. This reaction provides a facile access to an array of 4,5-dihydropyridazin-3(2H)-one derivatives, which are very promising in medicinal applications as potential biologically active candidates. Notably, these dihydropyridazinones could also be synthesizedviaa one-pot reaction protocol by using thein situformed azlactones fromN-acyl amino acids andin situgenerated azoalkenes from α-halogeno hydrazones. The potential applications of the methodology were also demonstrated by gram-scale experiments and the versatile conversions of the products into other nitrogen-containing compounds.