Categories: Synthesis of N-Heterocycles >
Synthesis of dihydropyridines
Name Reactions
Hantzsch Dihydropyridine Synthesis
Recent Literature
Treatment of 6-alkoxy-1,4,5,6-tetrahydropyridines with neutral alumina (activity
grade I) suspended in refluxing acetonitrile, afforded 1,4-dihydropyridines in
excellent yields. This method allowed an efficient synthesis of
5,6-unsubstituted dihydropyridines, which are difficult to prepare by
traditional methods, from acyclic and readily available precursors.
S. Maiti, J. C. Menéndez, Synlett, 2009,
2249-2252.
Metal perchlorates act as Lewis acid catalysts for the synthesis of
1,2,3,4-tetrasubstituted 1,4-dihydropyridines from enamino or carbonylic
derivatives in moderate yields.
G. Bartoli, K. Babiuch, M. Bosco, A. Carlone, P. Galzerano, P. Melchiorre, L.
Sambri, Synlett, 2007,
2897-2901.
HCl, generated in situ from 2,4,6-trichloro[1,3,5]triazine (TCT, cyanuric
chloride), catalyzed a solvent free Hantzsch reaction at room temperature
with enhanced reaction rates. The reaction conditions allow facile
preparation of glycoconjugates of dihydropyridines under mild reaction
conditions in high yields.
G. V. M. Sharma, K. L. Reddy, P. S. Lakshmi, P. R. Krishna, Synthesis, 2006, 55-58.
Covalently Anchored Sulfonic Acid on Silica Gel as an Efficient and Reusable
Heterogeneous Catalyst for the One-Pot Synthesis of Hantzsch
1,4-Dihydropyridines under Solvent-Free Conditions
R. Gupta, R. Gupta, S. Paul, A. Loupy, Synthesis, 2007,
2835-2838.
Manganese mediates a direct functionalization of Hantzsch esters with readily
accessible alkyl iodides through an aromatization–dearomatization strategy to
provide valuable 4-alkyl-1,4-dihydropyridines in good yields under visible-light
irradiation at room temperature. The reacton displays high functional-group
compatibility and is applicable for gram-scale synthesis and late-stage
functionalization.
X.-G. Liu, C.-S. Dong, F. Li, B. Zhang, Org. Lett., 2021, 23,
4002-4007.
An aluminum chloride promoted Hantzsch reaction of a wide range of N-tosylhydrazones
provides a series of 1,4-dihydropyridines (1,4-DHPs) in good yields.
H. Wang, M. Tang, Synthesis, 2017,
49, 4893-4898.
Hantzsch 1,4-dihydropyridine and polyhydroquinoline derivatives were synthesized
in excellent yields in aqueous micelles. The reaction is catalyzed by PTSA and
strongly accelerated by ultrasonic irradiation.
A. Kumar, R. A. Maurya, Synlett, 2008,
883-885.
Facile Yb(OTf)3 promoted one-pot synthesis of polyhydroquinoline derivatives
through Hantzsch reaction
L.-M. Wang, J. Sheng, L. Zhang, J.-W. Han, Z.-Y. Fan, H. Tian, C.-T. Qian, Tetrahedron, 2005,
61, 1539-1543.