Full Paper

Multicomponent Reactions of 1,3-Cyclohexanediones and Formaldehyde in Glycerol: Stabilization of Paraformaldehyde in Glycerol Resulted from using Dimedone as Substrate

  1. Minghao Li1,
  2. Chang Chen1,
  3. Fei He1,
  4. Yanlong Gu1,2

Article first published online: 9 FEB 2010

DOI: 10.1002/adsc.200900770

Issue

Advanced Synthesis & Catalysis

Advanced Synthesis & Catalysis

Volume 352, Issue 2-3, pages 519–530, February 15, 2010

Additional Information

How to Cite

Li, M., Chen, C., He, F. and Gu, Y. (2010), Multicomponent Reactions of 1,3-Cyclohexanediones and Formaldehyde in Glycerol: Stabilization of Paraformaldehyde in Glycerol Resulted from using Dimedone as Substrate. Adv. Synth. Catal., 352: 519–530. doi: 10.1002/adsc.200900770

Author Information

  1. 1

    Institute of Physical Chemistry and Industrial Catalysis, School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology (HUST), 1037 Luoyu road, Hongshan District, Wuhan 430074, People's Republic of China, Fax: (+86)-(0)27-8754-4532

  2. 2

    Hubei Key Laboratory of Material Chemistry and Service Failure, Huazhong University of Science and Technology, Wuhan 430074, People's Republic of China

Publication History

  1. Issue published online: 17 FEB 2010
  2. Article first published online: 9 FEB 2010
  3. Manuscript Received: 5 NOV 2009

Funded by

  • National Natural Science Fundation of China. Grant Number: 20903042
  • Program for new Centzry Excellent Talents in the University of China
  • Chutian Scholar Program of Hubei Provincial Government

SEARCH

SEARCH BY CITATION

ARTICLE TOOLS

View Full Article with Supporting Information (HTML) Get PDF (326K)

Keywords:

  • 1,3-cyclohexandione derivatives;
  • formaldehyde;
  • glycerol;
  • multicomponent reaction;
  • tandem Knoevenagel/hetero-Diels–Alder reaction

Abstract

Glycerol has proved to be an effective promoting medium for many multicomponent reactions of 1,3-cyclohexanediones and formaldehyde. Styrenes, amines, 2-naphthol, 4-hydroxy-6-methyl-2-pyrone and 4-hydroxy-1-methyl-2-quinolone could easily react with 1,3-cyclohexanediones and paraformaldehyde in glycerol under catalyst-free conditions to afford a variety of complex skeletons in fair to excellent yields. In these reactions, glycerol not only showed a significant promoting effect on the reaction yields but also endowed the reaction system with many typical properties of green chemistry, such as cheap, renewable, recyclable and biodegradable solvent, good safety and easy separation of product. The promoting effect of glycerol for the three-component reaction of styrene, dimedone and paraformaldehyde could be attributed to a restricted formation of the methylene intermediate in glycerol. During the reaction, a physical shell, which is mainly composed of a by-product generated in the beginning of the reaction, might be formed in the surface of paraformaldehyde and plays a key role in controlling the formation of the intermediate by means of restricting the decomposition of paraformaldehyde.

View Full Article with Supporting Information (HTML) Get PDF (326K)