Synthesis of 2-Aryl-3-sulfonylchromans via Knoevenagel Condensation and Reduction Protocol

The Journal of Organic Chemistry
Meng-Yang ChangYu-Hsin Chen

Abstract

In this article, a concise, easy-operational, and high-yield method for the synthesis of 2-aryl-3-sulfonylchromans is described by two-step routes: (i) NH4OAc mediated Knoevenagel condensation of β-ketosulfones and o-hydroxybenzaldehydes in a cosolvent of toluene and THF at reflux for 10 h, and (ii) NaBH4 promoted regio- and stereocontrolled reduction of the resulting 2-arylchromen-2-ols in a cosolvent of MeOH and THF at rt for 1 h. This protocol provides a highly effective (4+2) annulation via one carbon-oxygen and one carbon-carbon bond formations.

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Mar 13, 2003·Chemical Reviews·Douglas A HortonMark L Smythe
Oct 6, 2006·Organic Letters·Kelin LiJon A Tunge
Feb 4, 2011·Proceedings of the National Academy of Sciences of the United States of America·Darlene Q TanJared T Shaw
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Apr 14, 2015·The Journal of Organic Chemistry·Jan KumpfUwe H F Bunz

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Citations

Jan 23, 2021·The Journal of Organic Chemistry·Jun XuXiaogang Liu
Apr 23, 2021·Organic & Biomolecular Chemistry·Raju Jannapu ReddyJangam Jagadesh Kumar
Mar 15, 2018·Organic Letters·Meng-Yang ChangHan-Yu Chen
May 24, 2018·The Journal of Organic Chemistry·Meng-Yang Chang, Yu-Lin Tsai

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