Synthesis of [1,2,3]-Triazolo[5,1-a]-isoquinolines through TBAF-Promoted Cascade Reactions

Synthesis of [1,2,3]-Triazolo[5,1-a]-isoquinolines through TBAF-Promoted Cascade Reactions
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通过 TBAF 促进的级联反应合成[1,2,3]-三唑并[5,1-a]-异喹啉

DOI:
10.1002/ajoc.202000618
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发表时间:
2020-12-14
影响因子:
2.7
通讯作者:
Li, Chuan-Ying
Li, Chuan-Ying
中科院分区:
化学3区
文献类型:
--
作者:
Duan, Shengguo;Chen, Yidian;Li, Chuan-Ying

文献摘要

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采用四丁基氟化铵(TBAF)催化脱甲基环化级联反应合成了[1,2,3]-三唑[5,1- A]-异喹啉类化合物。大多数产物在温和条件下以优异的收率得到。通过稍微改变反应条件,也可以合成有价卤素取代的[1,2,3]-三唑[5,1-a]-异喹啉。通过脱氮反应可顺利得到功能化异喹啉类化合物。对照实验表明,TBAF和市售试剂中所含的水促进了这种转化。氘标记产物也容易得到,收率高。
A tetrabutylammonium fluoride (TBAF)-promoted detosylation cyclization cascade was developed for the synthesis of [1,2,3]-triazolo[5,1-a]-isoquinolines. Most of the products were obtained in excellent yields under mild conditions. Valuable halogen-substituted [1,2,3]-triazolo[5,1-a]-isoquinolines could also be synthesized with a slight modification of the reaction conditions. Functionalized isoquinolines were obtained smoothly by denitrogenative reactions. The control experiments showed that this transformation was facilitated by TBAF and the water contained in the commercially obtained reagent. Deuterium labeling products could also be obtained easily in high yield.