Palladium-catalyzed coupling of N-tosylhydrazones with ortho substituted aryl halides: synthesis of 4-arylchromenes and related heterocycles

TETRAHEDRON LETTERS

卷:52

Article

Rasolofonjatovo, Evelia¹  Treguier, Bret¹  Provot, Olivier¹  Hamze, Abdallah¹  Morvan, Estelle¹  Brion, Jean-Daniel¹  Alami, Mouad¹ 

[1] Univ Paris Sud, Fac Pharm, Chim Therapeut Lab, BioCIS,UMR 8076, F-92296 Chatenay Malabry, France

关键词: Palladium;    N-Tosylhydrazone;    Alkyne hydration;    Trisubstituted olefin;    Cyclization;    p-Toluenesulfonic acid;    Chromene;    Thiochromene;    Dihydrobenzo-oxepine;   

DOI  :  10.1016/j.tetlet.2010.12.093

来源: Elsevier

【 摘 要 】

A convenient and efficient procedure for the synthesis of 4-arylchromenes, thiochromenes, and related heterocycles via a four step-sequence has been developed. The first three steps, which involve hydration of alkynes, hydrazones formation, and their Pd-coupling with ortho substituted aryl halides, furnished stereoselectively Z-trisubstituted olefins without any purification of the intermediates generated in each stage. These latter proved to be suitable precursors, in the last step, for the synthesis of the desired heterocycles of biological interest. (C) 2011 Elsevier Ltd. All rights reserved.

【 授权许可】

Free