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ERIC Number: EJ918275
Record Type: Journal
Publication Date: 2010-Jun
Pages: 3
Abstractor: As Provided
Reference Count: 19
ISBN: N/A
ISSN: ISSN-0021-9584
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.)
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