Tetrahedron

Synthesis of stable azomethine ylides by the rearrangement of 1, 3-dipolar cycloadducts of 3, 4-dihydroisoquinoline-2-oxides with DMAD

N Coşkun, S Tunçman

Index: Coskun, Necdet; Tuncman, Selen Tetrahedron, 2006 , vol. 62, # 7 p. 1345 - 1350

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Citation Number: 26

Abstract

1-Aryl-6, 7-dimethoxy-1, 2, 3, 4-tetrahydroisoquinolines were prepared according to a one- pot procedure involving the reaction of 2-(3, 4-dimethoxyphenyl)-ethylamine with aromatic aldehydes in TFA at reflux. The tetrahydroisoquinolines were treated with H2O2–WO42− in methanol at room temperature to give the corresponding 3, 4-dihydroisoquinoline-2-oxides. Treatment of these cyclic nitrones with DMAD in toluene at room temperature gave the ...