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Comparing the Traditional with the Modern: A Greener, Solvent-Free Dihydropyrimidone Synthesis

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Evangelos Aktoudianakis , Elton Chan , Amanda R. Edward , Isabel Jarosz , Vicki Lee , Leo Mui , Sonya S. Thatipamala and Andrew P. Dicks

Department of Chemistry, University of Toronto, Toronto, ON M5S 3H6, Canada

J. Chem. Educ., 2009, 86 (6), p 730

DOI: 10.1021/ed086p730

Publication Date (Web): June 1, 2009

Section:

History, Education, and Documentation

Abstract

A microscale organic synthesis experiment is outlined where students undertake both a "traditional" and "modern" Biginelli preparation of a dihydropyrimidone, within the same three-hour session. Each method is straightforward, appropriate as part of a mid-level undergraduate laboratory, and performed individually or between a pair of students. Emphasis is placed on comparing approaches from a green chemistry perspective. The class probes concepts of catalytic reactivity, solvent-free synthesis, atom economy, and energy consumption to assess green improvements made by employing the modern strategy.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Laboratory Instruction

Keywords (Feature):

Green Chemistry

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Catalysis

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This article has been cited by 2 ACS Journal articles (2 most recent appear below).

Metal−Acetylacetonate Synthesis Experiments: Which Is Greener?
M. Gabriela T. C. Ribeiro and Adélio A. S. C. Machado
Journal of Chemical Education2011 Article ASAP
- Metal−Acetylacetonate Synthesis Experiments: Which Is Greener?
  M. Gabriela T. C. Ribeiro and Adélio A. S. C. Machado
  Journal of Chemical Education2011 Article ASAP
  A procedure for teaching green chemistry through laboratory experiments is presented in which students are challenged to use the 12 principles of green chemistry to review and modify synthesis protocols to improve greenness. A global metric, green star, ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Molecular Models from a Greener, Solvent-Free Synthesis. Biginelli Product, Ethyl Acetoacetate, Monastrol, and Nifedipine
William F. Coleman
Journal of Chemical Education2009 86 (6), 768
- Molecular Models from a Greener, Solvent-Free Synthesis. Biginelli Product, Ethyl Acetoacetate, Monastrol, and Nifedipine
  William F. Coleman
  Journal of Chemical Education2009 86 (6), 768
  Models added to JCE's Featured Molecules collection include monastrol, ethyl 1,2,3,4-tetrahydro-6-methyl-2-oxo-4-phenylpyrimidine-5-carboxylate (Biginelli product), and nifedipine.
  Abstract | Hi-Res PDF | PDF w/ Links

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Received: August 03, 2009

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Comparing the Traditional with the Modern: A Greener, Solvent-Free Dihydropyrimidone Synthesis