1165-06-6Relevant articles and documents
Accelerated Hantzsch electrospray synthesis with temporal control of reaction intermediates
Bain, Ryan M.,Pulliam, Christopher J.,Cooks, R. Graham
, p. 397 - 401 (2015)
Complex chemical reactions can occur in electrosprayed droplets on the millisecond time scale. The Hantzsch synthesis of 1,4-dihydropyridines was studied in this way using on-line mass spectral analysis to optimize conditions and characterize the product
An efficient and solvent-free one-pot synthesis of 1,4-dihydropyridines under microwave irradiation
Kuraitheerthakumaran,Pazhamalai,Gopalakrishnan
, p. 1199 - 1202 (2011)
An efficient synthesis of 1,4-dihydropyridines using lanthanum oxide as a catalyst from aldehydes, β-ketoester and ammonium acetate without solvent under the irradiation of microwave is described. Compared with the classical Hantzsch reaction, this new me
The multicomponent Hantzsch reaction: Comprehensive mass spectrometry monitoring using charge-tagged reagents
Santos, Vanessa G.,Godoi, Marla N.,Regiani, Thaís,Gama, Fernando H. S.,Coelho, Mirela B.,De Souza, Rodrigo O. M. A.,Eberlin, Marcos N.,Garden, Simon J.
, p. 12808 - 12816 (2014)
A novel strategy for the ESI-MS monitoring of reaction solutions involving the alternate use of permanently charge-tagged reagents has been used for comprehensive mass spectrometry monitoring of the multicomponent Hantzsch 1,4-dihydropyridine reaction. By placing a charge tag on either, or both, of the two key reactants, ion suppression effects for ESI were eliminated or minimized, and comprehensive detection of charge-tagged intermediates was achieved. The strategy allowed the trapping and characterization of the important intermediates in the mechanism for 1,4-dihydropyridine formation.
Photoinduced umpolung addition of carbonyl compounds with α,β-unsaturated esters enables the polysubstituted γ-lactone formation
Gu, Jia-Yi,Zhang, Wei,Jackson, Seth R.,He, Yan-Hong,Guan, Zhi
, p. 13441 - 13444 (2020)
We herein report the photoinduced intermolecular umpolung addition of aromatic ketones/aldehydes with α,β-unsaturated esters via ketyl radical intermediates. Following an intramolecular transesterification, a variety of γ-lactone derivatives are readily accessed. Mechanistic investigations demonstrate the significant role of Hantzsch ester, which serves both as the electron and proton donor. This journal is
Research on heterocyclic compounds. XLIII. Synthetic studies on 1,4-dihydropyridine derivatives
Rimoli, Maria Grazia,Avallone, Lucia,Zanarone, Serena,Abignente, Enrico,Mangoni, Alfonso
, p. 1117 - 1122 (2002)
In order to obtain N-benzyl-3,5-dicarbethoxy-2,6-dimethyl-4-phenyl-1,4-dihydropyridine 1 as a lead compound of pharmacological interest, the classical Hantzsch synthetic method and the modified Collie procedure were used. However, only a very low yield of
Unprecedented synthesis of hantzsch 1,4-dihydropyridines under biginelli reaction conditions
Yadav,Subba Reddy,Reddy
, p. 425 - 430 (2001)
Hantzsch 1,4-dihydropyridines are synthesized in high yields by a one-pot cyclocondensation of aldehyde, β-ketoester, and urea on the surface of silica gel under microwave irradiation in solvent-free conditions.
Silica (NPs) supported Fe (III) as a reusable heterogeneous catalyst for the one-pot synthesis of 1, 4-dihydropyridines under mild conditions
Safaei-Ghomi, Javad,Ziarati, Abolfazl,Zahedi, Safura
, p. 933 - 939,7 (2012)
A cheap and recyclable silica (NPs) supported Fe (III) was prepared as heterogeneous catalyst for the synthesis of various substituted 1,4-dihydropyridines via condensation of aldehydes with ethyl acetoacetate and ammonium acetate in ethanol. The products
Boosting the catalytic performance of manganese (III)-porphyrin complex MnTSPP for facile one-pot green synthesis of 1,4-dihydropyridine derivatives under mild conditions
Ali El-Remaily, Mahmoud Abd El Aleem Ali,Hamad, Hesham A.,Soliman, Ahmed M. M.,Elhady, Omar M.
, (2021/03/26)
In this study, the metal complex (5,10,15,20-tetrakis-(4-sulfonatophenyl)-porphyrin manganese (III) chloride; denoted as MnTSPP) represents a promising efficient and reusable heterogeneous solid catalyst for facile and highly efficient one-pot synthesis of 1,4 dihydropyridine derivatives via three-component condensation reaction of aromatic aldehyde, ethyl acetoacetate, and ammonium acetate under green and mild reaction conditions. The simple operation, short reaction time (15 min), and the high efficiency (99%) are the special advantage of this protocol. Furthermore, the green aspects of this synthetic protocol were more studied by examination of the reusability of MnTSPP for four consecutive cycles without a significant loss of catalytic activity. Remarkably, the new synthesis presented advantages in terms of safety, commercially available catalyst, simplicity, stability, mild conditions, short reaction time, and excellent yields, using a mixture of H2O and C2H5OH environmental-friendly solvent, operationally facile, wide tolerance of starting materials, and excellent recoverable of the catalyst.
Urea as an ammonia surrogate in the hantzsch’s synthesis of polyhydro-quinolines / 1,4-dihydropyridines under green reaction conditions
Anna, Venkateswara Rao,Dhananjaya, G.,Mahesh Kumar, P.,Narayana Murthy, V.,Pal, Manojit,Pulla Reddy, S.,Raghunadh, Akula
supporting information, p. 226 - 232 (2021/03/19)
Synthesis of polyhydroquinolines via Hantzsch’s multicomponent reaction (MCR) involves the use of a hygroscopic and moderately toxic ammonium salt as one of the key reactants. In our effort, we have found urea as an effective ammonia surrogate when the MC