Prev. Article Next Article Table of Contents

Article

Condensation of α-Aroylketene Dithioacetals and 2-Hydroxyarylaldehydes Results in Facile Synthesis of a Combinatorial Library of 3-Aroylcoumarins^#

Supporting Info

H. Surya Prakash Rao* and S. Sivakumar

Department of Chemistry, Pondicherry University, Pondicherry 605 014, India

J. Org. Chem., 2006, 71 (23), pp 8715–8723

DOI: 10.1021/jo061372e

Publication Date (Web): October 11, 2006

Ketene Acetal Chemistry: Part 4; see ref 12c.

To whom correspondence should be addressed. E-mail: hspr@yahoo.com. Fax: +91 413 2655987.

, hspr@yahoo.com

Abstract

A facile, convenient, efficient, and high yielding synthesis of a combinatorial library of 3-aroylcoumarins has been developed by the condensation of easily available α-aroylketene dithioacetals (AKDTAs) and 2-hydroxybenzaldehydes (salicylaldehydes)/2-hydroxy-1-naphthaldehyde in the presence of catalytic amount of piperidine in THF reflux. The condensation of ferrocene derived α-aroylketene dithioacetal and 2-hydroxybenzaldehyde furnished coumarin installed on a ferrocene platform.

View: Full Text HTML | Hi-Res PDF

Tools

SciFinder Links

History

Published In Issue November 10, 2006
Received July 2, 2006

Recommend & Share

Related Content

Palladium-Catalyzed Carbonylative Annulation of Internal Alkynes: Synthesis of 3,4-Disubstituted CoumarinsThe Journal of Organic Chemistry
- Palladium-Catalyzed Carbonylative Annulation of Internal Alkynes: Synthesis of 3,4-Disubstituted Coumarins
  Dmitry V. Kadnikov and Richard C. Larock
  The Journal of Organic Chemistry 2003 68 (24), pp 9423–9432
  Abstract: The palladium-catalyzed annulation of internal alkynes by o-iodophenols in the presence of CO results in exclusive formation of coumarins. No isomeric chromones have been observed. The best reaction conditions utilize the 2-iodophenol, 5 equiv of alkyne, ...
  Abstract | Full Text HTML | Hi-Res PDF
[5 + 1] Annulation: A Synthetic Strategy for Highly Substituted Phenols and CyclohexenonesJournal of the American Chemical Society
- [5 + 1] Annulation: A Synthetic Strategy for Highly Substituted Phenols and Cyclohexenones
  Xihe Bi, Dewen Dong, Qun Liu, Wei Pan, Lei Zhao, and Bing Li
  Journal of the American Chemical Society 2005 127 (13), pp 4578–4579
  Abstract: A novel [5 + 1] annulation strategy is developed for the synthesis of highly substituted phenols and cyclohexenones from α-alkenoyl ketenedithioacetals and nitroalkanes.
  Abstract | Full Text HTML | Hi-Res PDF

Article

Condensation of α-Aroylketene Dithioacetals and 2-Hydroxyarylaldehydes Results in Facile Synthesis of a Combinatorial Library of 3-Aroylcoumarins^#