1,4-Dihydropyridine

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1,4-Dihydropyridine
1,4-Dihydropyridine.png
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Names
Preferred IUPAC name
1,4-Dihydropyridine [1]
Identifiers
3D model (JSmol)
ChemSpider
MeSH 1,4-dihydropyridine
PubChem CID
UNII
  • InChI=1S/C5H7N/c1-2-4-6-5-3-1/h2-6H,1H2 Yes check.svgY
    Key: YNGDWRXWKFWCJY-UHFFFAOYSA-N Yes check.svgY
  • C1C=CNC=C1
Properties
C
5H
7N
Molar mass 81.1158 g mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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1,4-Dihydropyridine (DHP) is an organic compound with the formula CH2(CH=CH)2NH. The parent compound is uncommon, [2] but derivatives of 1,4-dihydropyridine are important commercially and biologically. The pervasive cofactors NADH and NADPH are derivatives of 1,4-dihydropyridine. Dihydropyridine calcium channel blockers are a class of L-type calcium channel blockers used in the treatment of hypertension. 1,2-Dihydropyridines are also known. [3] [4]

Contents

Properties and reactions

A recurring feature of 1,4-dihydropyridines is the presence of substituents at the 2- and 6-positions. Dihydropyridines are enamines, which otherwise tend to tautomerize or hydrolyze.[ citation needed ]

The dominant reaction of dihydropyridines is their ease of oxidation. In the case of dihydropyridines with hydrogen as the substituent on nitrogen, oxidation yields pyridines:

CH2(CH=CR)2NH → C5H3R2N + H2

The naturally occurring dihydropyridines NADH and NADPH contain N-alkyl groups. Therefore, their oxidation does not yield pyridine, but N-alkylpyridinium cations:

CH2(CH=CR)2NR' → C5H3R2NR' + H−

Hantzsch ester

Chemical structure of Hantzsch's ethyl ester, a well-known dihydropyridine. HantzschEster.svg
Chemical structure of Hantzsch's ethyl ester, a well-known dihydropyridine.

Hantzsch ester [5]

See also

References

  1. ↑ "1,4-dihydropyridine - Compound Summary". Pubchem Compound. US: National Center for Biotechnology Information. 27 March 2005. Identification and Related Records. Retrieved 1 November 2011.
  2. ↑ Duburs, Gunãrs; Sausins, Alvils (1988). "Synthesis of 1,4-Dihydropyridines by Cyclocondensation Reactions". Heterocycles. 27: 269. doi: 10.3987/REV-87-370 .
  3. ↑ Stout, David M.; Meyers, A. I. (1982). "Recent advances in the chemistry of dihydropyridines". Chemical Reviews. 82 (2): 223–243. doi:10.1021/cr00048a004.
  4. ↑ Lavilla, Rodolfo (2002). "Recent developments in the chemistry of dihydropyridines". Journal of the Chemical Society, Perkin Transactions 1 (9): 1141–1156. doi:10.1039/B101371H.
  5. ↑ Cheung, Lawrence L. W.; Styler, Sarah A.; Dicks, Andrew P. (2010). "Rapid and Convenient Synthesis of the 1,4-Dihydropyridine Privileged Structure". Journal of Chemical Education. 87 (6): 628–630. Bibcode:2010JChEd..87..628C. doi:10.1021/ed100171g.
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