Reaction of 5-aryloxazolidines with arylmagnesium bromides as a new route to N-benzyl-β-hydroxyphenethylamines as starting materials for the preparation of 4-aryl-1,2,3,4-tetrahydroisoquinolines

TETRAHEDRON LETTERS

卷:54

Article

Moshkin, Vladimir S.¹  Sosnovskikh, Vyacheslav Ya.¹ 

[1] Ural Fed Univ, Dept Chem, Ekaterinburg 620000, Russia

关键词: 4-Aryl-1,2,3,4-tetrahydroisoquinolines;    5-Aryloxazolidines;    Non-stabilized azomethine ylide;    [3+2] Cycloaddition;    Cyclization reaction;   

DOI  :  10.1016/j.tetlet.2013.03.076

来源: Elsevier

【 摘 要 】

Benzaldehydes react smoothly with the non-stabilized azomethine ylide derived from sarcosine and formaldehyde to form 5-aryloxazolidines as intermediates, which undergo ring-opening to give N-benzyl-beta-hydroxyphenethylamines in good yields by the action of arylmagnesium bromides. Their subsequent acid-catalyzed cyclization into 4-aryl-1,2,3,4-tetrahydroisoquinolines was performed in moderate to good yields. (c) 2013 Elsevier Ltd. All rights reserved.

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