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The Biginelli Reaction
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Abstract
The utilization of the Biginelli reaction, a one-pot condensation of an aldehyde, a β-keto ester, and urea, is described. This reaction involves a number of individual steps, each of which is accessible to first-year organic students. The product, a 3,4-dihydropyrimidinone, is a member of a medicinally useful class of compounds. The reaction is simple to perform and the product precipitates from solution in an extremely pure form.
Keywords (Audience):
Second-Year UndergraduateKeywords (Domain):
Laboratory InstructionKeywords (Feature):
The Microscale LaboratoryKeywords (Pedagogy):
Hands-On Learning / ManipulativesKeywords (Subject):
Microscale LabCiting Articles
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This article has been cited by 6 ACS Journal articles (5 most recent appear below).
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Desiree E. Mendes and Allen M. SchoffstallJournal of Chemical Education2011 88 (11), 1582-1585Citrus Peel Additives for One-Pot Triazole Formation by Decarboxylation, Nucleophilic Substitution, and Azide–Alkyne Cycloaddition Reactions
Desiree E. Mendes and Allen M. SchoffstallJournal of Chemical Education2011 88 (11), 1582-1585This undergraduate organic laboratory experiment consists of three different reactions occurring in the same flask: a cycloaddition reaction, preceded by decarboxylation and nucleophilic substitution reactions. The decarboxylation and cycloaddition ...
Rapid and Convenient Synthesis of the 1,4-Dihydropyridine Privileged Structure
Lawrence L. W. Cheung, Sarah A. Styler and Andrew P. DicksJournal of Chemical Education2010 87 (6), 628-630Rapid and Convenient Synthesis of the 1,4-Dihydropyridine Privileged Structure
Lawrence L. W. Cheung, Sarah A. Styler and Andrew P. DicksJournal of Chemical Education2010 87 (6), 628-630A short, semi-microscale synthesis of two 1,4-dihydropyridine drug analogues via a Hantzsch reaction is described, which is appropriate for a second-year undergraduate organic laboratory. Products are specifically chosen to highlight the biological ...
Comparing the Traditional with the Modern: A Greener, Solvent-Free Dihydropyrimidone Synthesis
Evangelos Aktoudianakis , Elton Chan , Amanda R. Edward , Isabel Jarosz , Vicki Lee , Leo Mui , Sonya S. Thatipamala and Andrew P. DicksJournal of Chemical Education2009 86 (6), 730Comparing the Traditional with the Modern: A Greener, Solvent-Free Dihydropyrimidone Synthesis
Evangelos Aktoudianakis , Elton Chan , Amanda R. Edward , Isabel Jarosz , Vicki Lee , Leo Mui , Sonya S. Thatipamala and Andrew P. DicksJournal of Chemical Education2009 86 (6), 730A 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-...
Incorporating Guided-Inquiry Learning into the Organic Chemistry Laboratory
Allen M. Schoffstall , Barbara A. GaddisJournal of Chemical Education2007 84 (5), 848Incorporating Guided-Inquiry Learning into the Organic Chemistry Laboratory
Allen M. Schoffstall , Barbara A. GaddisJournal of Chemical Education2007 84 (5), 848Informed science educators who are responsible for undergraduate laboratory programs strive to improve the effectiveness of learning in the laboratory. Guided-inquiry learning in the laboratory is one reasonable alternative (among others described here) ...
The State of Organic Teaching Laboratories
Gail HorowitzJournal of Chemical Education2007 84 (2), 346The State of Organic Teaching Laboratories
Gail HorowitzJournal of Chemical Education2007 84 (2), 346This review explores the dramatic changes that have taken place in the organic chemistry laboratory course over the last two to three decades. The most significant changes have been in the areas of pedagogy and technology. Significant inroads have been ...
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- Received: August 03, 2009
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