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Synthetic approaches to N- and 4-substituted 1,4-dihydro-3(2H)-isoquinolinone derivatives
Tetrahedron ( IF 2.1 ) Pub Date : 2021-09-22 , DOI: 10.1016/j.tet.2021.132455
Michael J. O’ Sullivan 1 , Richard J.D. Hatley 2 , Christopher R. Wellaway 2 , Sean P. Bew 1 , Christopher J. Richards 1
Affiliation  

Reaction of methyl-2-(2-formylphenyl)acetate with primary amines in a reductive amination/cyclisation process resulted in N-substituted 1,4-dihydro-3(2H)-isoquinolinones. With H2NCH2R sodium borohyride is a suitable reductant (11 examples), but H2NCHR1R2 required a transfer hydrogenation using ammonium formate catalysed by palladium on carbon (9 examples). 4-Substituted-1,4-dihydro-3(2H)-isoquinolinones were synthesised by deprotonation (n-butyllithium) and addition of R3CH2Br (12 examples with R3 = alkyl, Ar, CHdouble bondCH2, Ctriple bondCH). Modest diastereoselectivity was achieved with 1,4-dihydro-3(2H)-isoquinolinones derived from H2NCHMeR2 [R2 = (η5-C5H4)Co(η4-C4Ph4) - max. dr = 1.9 : 1], but use of H2NCHMeFc (Fc = ferrocenyl) provided a new method of 1,4-dihydro-3(2H)-isoquinolinone N-deprotection with formic acid.



中文翻译:

N-和4-取代的1,4-二氢-3(2H)-异喹啉酮衍生物的合成方法

在还原胺化/环化过程中,2-(2-甲酰基苯基)乙酸甲酯与伯胺的反应产生N-取代的 1,4-二氢-3(2H)-异喹啉酮。H 2 NCH 2 R 硼氢化钠是合适的还原剂(11 个实施例),但 H 2 NCHR 1 R 2需要使用由披钯碳催化的甲酸铵进行转移氢化(9 个实施例)。通过去质子化(丁基锂)和添加 R 3 CH 2 Br(12 个实例,其中 R 3  = 烷基、Ar、CH 双键CH 2、C )合成了 4-取代的-1,4-二氢-3(2H)-异喹啉酮三键CH)。使用衍生自 H 2 NCHMeR 2 [R 2  = (η 5 -C 5 H 4 )Co(η 4 -C 4 Ph 4 ) - max. 的1,4-二氢-3(2H)-异喹啉酮获得适度的非对映选择性。dr = 1.9 : 1],但使用 H 2 NCHMeFc(Fc = 二茂铁)提供了一种用甲酸进行 1,4-二氢-3(2H)-异喹啉酮N-脱保护的新方法。

更新日期:2021-10-29
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