Development of Triazinone-Based Condensing Reagents for Amide Formation
Development of Triazinone-Based Condensing Reagents for Amide Formation
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DOI：
10.1021/acs.joc.9b01261
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发表时间：
2019-12-06
影响因子：
3.6
通讯作者：
Kunishima，Munetaka
中科院分区：
文献类型：
--
作者：
Yamada，Kohei;Kota，Mika;Kunishima，Munetaka
已经开发出新型三嗪酮缩合试剂。钯催化的 2-(烯丙氧基)-4,6-二氯-1,3,5-三嗪发生 O-N 烯丙基重排，随后使用醇和胺进行区域选择性取代，得到氯三嗪酮，可以使用 N-甲基吗啉轻松将其转化为相应的缩合试剂。使用这些试剂进行羧酸和胺的缩合，以良好的产率提供所需的酰胺。与4-(4,6-二甲氧基-1,3,5-三嗪-2-基)-4-甲基吗啉氯化物相比，新合成的三嗪酮基缩合试剂表现出更高的反应活性。
Novel triazinone-based condensing reagents have been developed. The palladium-catalyzed O–N allylic rearrangement of 2-(allyloxy)-4,6-dichloro-1,3,5-triazine and subsequent regioselective substitution using alcohols and an amine afforded chlorotriazinones, which can be readily converted usingN-methylmorpholine into the corresponding condensing reagents. The condensation of carboxylic acids and amines using these reagents proceeded to afford the desired amides in good yields. In comparison with 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride, the newly synthesized triazinone-based condensing reagents exhibited higher reactivity.