Synthesis of tetrahydrobenzoisoquinolinols, tetrahydropyrindines, and hexahydroquinolines from 4-aryltetrahydropyridines
摘要:
A straightforward synthesis of tetrahydrobenzoisoquinolinols 2, tetrahydropyrindines 3, and hexahydroquinolines 4 from versatile intermediate 6 is reported. Two key transformations were carried out by intramolecular Friedel-Crafts cyclization and ring-closing metathesis in moderate yields. Skeleton 6 was easily prepared from the known starting material 4-aryl-4-methoxypiperidin-3-ones 7 via Wittig olefination with Ph3P=CHCO2Et, deconjugation with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), and boron trifluoride etherate (BF3-OEt2)-catalyzed addition of the corresponding iminium ion with allyltrimethylsilane. (C) 2011 Elsevier Ltd. All rights reserved.
DOI:
10.1016/j.tet.2011.04.089
作为产物:
描述:
在
Jones reagent 作用下,
以
丙酮 为溶剂,
以89%的产率得到4-methoxy-4-phenyl-1-(phenylsulfonyl)piperidin-3-one
参考文献:
名称:
Selenium dioxide-mediated methoxyhydroxylation of cyclic arylolefin
摘要:
Selenium dioxide-mediated methoxyhydroxylation of cyclic arylolefin with the modest yields is described. This facile strategy was also used to synthesize several 4-arylpyridines, 3-hydroxy-4-arylpyridines, and 3,4-diarylpyridines. Crown Copyright (C) 2010 Published by Elsevier Ltd. All rights reserved.