Chemodivergent synthesis of functionalized methanodibenzo[b,f][1,5]diazocin-13-ylmethanones and tetrahydroquinolines via solvent-dependent AB2 and A2B2 multicomponent annulation reactions,Organic Chemistry Frontiers

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Chemodivergent synthesis of functionalized methanodibenzo[b,f][1,5]diazocin-13-ylmethanones and tetrahydroquinolines via solvent-dependent AB2 and A2B2 multicomponent annulation reactions
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2020-05-19 , DOI: 10.1039/d0qo00449a
Isravel Muthukrishnan _{1,

2,

3,

4,

5} , Muthu Karuppasamy _{1,

2,

3,

4,

5} , B. S. Vachan _{1,

2,

3,

4,

5} , Diksha Rajput _{5,

6,

7,

8} , Nagarajan Subbiah _{1,

5,

9,

10} , C. Uma Maheswari _{1,

2,

3,

4,

5} , Vellaisamy Sridharan _{1,

2,

3,

4,

5}

Affiliation

A solvent-dependent chemodivergent approach was established for the synthesis of 6,12-methanodibenzo[b,f][1,5]diazocin-13-ylmethanones and 2,3,4-trisubstituted 1,2,3,4-tetrahydroquinolines involving two distinct multicomponent processes under basic conditions. The AB₂ three-component and A₂B₂ four-component reactions between 2-aminoarylaldehydes and aryl methyl ketones under basic conditions afforded 6,12-methanodibenzo[b,f][1,5]diazocin-13-ylmethanones (up to 95% yield) and trisubstituted tetrahydroquinolines (up to 84% yield), respectively, based on the nature of the solvent employed. The skeletal diversity and complexity were attained in these high atom- and step-economical processes by creating four new bonds in a single synthetic operation from readily available simple starting materials.

中文翻译：

通过溶剂依赖性AB2和A2B2多组分环化反应化学合成功能化的甲烷二苯并[b，f] [1,5]二唑-13-基甲烷酮和四氢喹啉

建立了一种溶剂依赖性化学发散方法，用于合成6,12-甲二苯并[ b，f ] [1,5]重氮素-13-基甲酮和2,3,4-三取代的1,2,3,4-四氢喹啉在基本条件下有两个不同的多组分过程。在碱性条件下，2-氨基芳基醛与芳基甲基酮之间的AB ₂三组分和A ₂ B ₂四组分反应得到6,12-甲二苯并[ b，f基于所用溶剂的性质，分别具有] [1,5]重氮素-13-基甲烷酮（产率高达95％）和三取代四氢喹啉（产率高达84％）。在这些高原子和分步经济的方法中，骨骼的多样性和复杂性是通过使用容易获得的简单起始原料在单个合成操作中创建四个新键来实现的。

更新日期：2020-06-30

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