ERIC Number: EJ918275
Record Type: Journal
Publication Date: 2010-Jun
Pages: 3
Abstractor: As Provided
ISBN: N/A
ISSN: ISSN-0021-9584
EISSN: N/A
Rapid and Convenient Synthesis of the 1,4-Dihydropyridine Privileged Structure
Cheung, Lawrence L. W.; Styler, Sarah A.; Dicks, Andrew P.
Journal of Chemical Education, v87 n6 p628-630 Jun 2010
A 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 relevance of this compound type while introducing the notion of a privileged structure. 1,4-Dihydropyridines are bioactive as calcium channel blockers and antioxidants and are lead candidates in the treatment of various medical conditions. Students generate one substituted 1,4-dihydropyridine by an operationally simple process and characterize it by melting point measurements, IR spectroscopy, and [superscript 1]H and [superscript 13]C NMR spectroscopy. This provides a springboard to discuss concepts of green chemistry, structure-activity relationships, conformational analysis, and related synthetic approaches. (Contains 1 figure, 1 scheme and 5 notes.)
Descriptors: Spectroscopy, Chemistry, Science Instruction, Scientific Principles, Biology, Molecular Structure, Organic Chemistry, College Science, Science Experiments, Science Laboratories, Undergraduate Study
Division of Chemical Education, Inc and ACS Publications Division of the American Chemical Society. 1155 Sixteenth Street NW, Washington, DC 20036. Tel: 800-227-5558; Tel: 202-872-4600; e-mail: eic@jce.acs.org; Web site: http://pubs.acs.org/jchemeduc
Publication Type: Journal Articles; Reports - Descriptive
Education Level: Higher Education
Audience: N/A
Language: English
Sponsor: N/A
Authoring Institution: N/A
Grant or Contract Numbers: N/A