Sequential amino-claisen rearrangement/intramolecular 1,3-dipolar cycloaddition/reductive cleavage approach to the stereoselective synthesis of cis-4-hydroxy-2-aryl-2,3,4,5-tetrahydro-1(1H)-benzazepines

被引：42

作者：

Ayala, Sandra Liliana Gomez

Stashenko, Elena

Palma, Alirio ^{[1
]}

Bahsas, Ali

Amaro-Luis, Juan Manuel

机构：

[1] Univ Ind Santander, Escuela Quim, Ctr Invest Biomol, Lab Sintesis Organ, Bucaramanga AA 678, Colombia

[2] Univ Los Andes, Dept Quim, Grp Prod Nat, Lab RMN, Merida 5101, Venezuela

来源：

SYNLETT | 2006年 / 14期

关键词：

amino-Claisen rearrangement; intramolecular 1,3-dipolar cycloaddition; tetrahydro-1-benzazepines; ortho-allylanilines; reductive cleavage;

D O I：

10.1055/s-2006-949654

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel stereoselective synthesis of cis-2-aryl-4-hydroxy-2,3,4,5-tetrahydro-1-benzazepines from N-allylanilines utilizing aromatic amino-Claisen rearrangement and intramolecular 1,3-dipolar cycloaddition methodologies is described. This sequence involves N-allylation of corresponding N-benzylanilines followed by amino-Claisen rearrangement, subsequent oxidation with in situ 1,3-dipolar cycloaddition affording isoxazolidines, and finally reductive cleavage of the isoxazolidinic N-O bond.

引用

页码：2275 / 2277

页数：3

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