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Palladium-catalyzed regio- and stereoselective synthesis of aryl and 3-indolyl-substituted 4-methylene-3,4-dihydroisoquinolin-1(2H)-ones.
Beilstein Journal of Organic Chemistry ( IF 2.2 ) Pub Date : 2020-05-20 , DOI: 10.3762/bjoc.16.95
Valeria Nori 1 , Antonio Arcadi 1 , Armando Carlone 1 , Fabio Marinelli 1 , Marco Chiarini 2
Affiliation  

Cascade cyclocarbopalladation of the readily available aryl/alkyl-substituted propargylic amides containing an aryl iodide moiety, followed by Suzuki–Miyaura coupling with arylboronic acids, allowed an efficient regio- and stereoselective synthesis of tetrasubstituted 4-methylene-3,4-dihydroisoquinolin-1(2H)-ones. Moreover, cascade cyclocarbopalladation, followed by the reaction with 2-alkynyltrifluoroacetanilides, accomplished a double cyclization to afford challenging 4-methylene-3,4-dihydroisoquinolin-1(2H)-ones bearing a 3-indolyl substituent through aminopalladation/reductive elimination.

中文翻译:

钯催化的芳基和3-吲哚基取代的4-亚甲基-3,4-二氢异喹啉-1(2H)-的区域和立体选择性合成。

容易获得的含芳基碘基团的芳基/烷基取代的炔丙基酰胺的级联环碳缩合反应,然后将Suzuki-Miyaura与芳基硼酸偶合,可实现区域和立体选择性合成四取代的4-亚甲基-3,4-二氢异喹啉-1 (2 H)-个。此外,级联环羰缩钯反应,然后与2-炔基三氟乙酰苯胺反应,完成了双环化反应,从而通过氨基palpalation /还原消除作用,使带有3-吲哚基取代基的4-亚甲基-3,4-二氢异喹啉-1(2 H)-具有挑战性。
更新日期:2020-05-20
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