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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 22, 1992 - Issue 1
66
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Original Articles

Nucleophilic Substitution in the Azomethine Series: An Improved Synthesis of 1,4-Dihydropyridines

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Pages 47-61 | Received 01 Jul 1991, Published online: 23 Sep 2006

References

  • Bossert , F. and Veter , W. U.S. Pat. 3 485 847 . 1969 Dec 23 . In the Hantzsch synthesis of Nifedipine one mol of an aldehyde is made to react with two moles of an alkyl acetoacetate in the presence of excess ammonia to obtain 1,4-dihydropyridines
  • Hantzsch . 1882 . Liebigs Ann. Chem. , 1 : 215 This patent specification also includes the appreciation of the pharmaceutical importance of this compound
  • Teller , Werner . B.R.D. Pat. Offenlegungs-schrift DE 33 12216 A1 C 07 D 211/90 . 1985 Apr 5 . The reaction where the ylidene is reacted with the alkyl 3-aminocrotonate can be found in the literature under very different names; Knoevenagel, Knoevenagel - Ruschaupt, Hantasch - Beyer, “Mixed Hantzsch Synthesis”, et. al. See
  • Knoevenagel . 1898 . Ber. Dtsch. Chem. Ges. , 31 : 743
  • Torre , K. 1964 . J. Org. Chem. , 29 : 3102
  • Meyer , H. Bossert , F. 1981 . Arzneim.-Forsch/Drug Res. , 31 ( I ) : 407 Nr. 3. In our opinion the most favourable name will be “The Knoevenagel synthesis” because of the confused authors situation. However, the mechanism of this reaction is a classical Michael addition's mechanism. See above under 2. b)
  • Benkó , P. , Bózsing , D. Lévai , L. B.R.D. Pat. Offenlegungsschrift DE 3 907 508 A1 C 07 119/10, C 07 D 211/90, C 07 D 251/04 . 1988 Marc 8, 1988 Aug 2 . Our patent specification relating to Nifedipine contains also the description of the preparing of these new starting compounds
  • Lyubomir , D. 1989 . C. Raev… etc., Arch. Pharm. (Weinheim) , : 253 The same amino adduct is mentined in the paper

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