1165-06-6Relevant academic research and scientific papers
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
A highly efficient magnetic solid acid nanocatalyst for the synthesis of new bulky heterocyclic compounds
Nasr-Esfahani, Masoud,Rafiee, Zahra,Montazerozohori, Morteza,Kashi, Hassan
, p. 47298 - 47313 (2016)
Fe3O4 nanoparticles were prepared and coated with 3-aminopropyltriethoxysilane (APTES). The formed amine-surfaced Fe3O4@APTES NPs were further chemically modified with maleic anhydride (MAH) to generate Fe3O4@APTES·MAH NPs. This catalyst was characterized by FT-IR, X-ray diffraction (XRD), scanning electron microscopy (SEM), transmission electron microscopy (TEM), thermogravimetric analysis (TG), energy dispersive X-ray analyzer (EDAX), vibrating sample magnetometry (VSM) and the dynamic light scattering (DLS) measurement technique. The catalyst showed high thermal stability and good reusability. Some new bulky heterocyclic compounds such as bis(2,4,5-triarylimidazole), bis(1,4-dihydropyridine), bis(1,8-dioxooctahydroxanthene) and bis(1,8-dioxo-decahydroacridine) derivatives were synthesized using 4,4′-(alkylazanediyl)dibenzaldehyde as substrate and Fe3O4@APTES or Fe3O4@APTES·MAH as catalyst. The high purity products were isolated and the catalyst was easily separated with a simple work-up with magnetic field and was recycled several times without noticeable loss of reactivity under the described reaction conditions.
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 SBA-15/SO3H nanoreactor as a highly efficient and reusable catalyst for diketene-based, four-component synthesis of polyhydroquinolines and dihydropyridines under neat conditions
Rostamnia, Sadegh,Pourhassan, Fatemeh
, p. 401 - 403 (2013)
An efficient diketene ring-opening synthesis of polyhydroquinoline derivatives using SBA-15 sulfonic acid modified mesoporous substrates a green and reusable catalyst in a single-pot four-component coupling reaction of diketene, alcohol, enamine, and alde
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.
Diketene-based neat four-component synthesis of the dihydropyrimidinones and dihydropyridine backbones using silica sulfuric acid (SSA)
Rostamnia, Sadegh,Lamei, Kamran
, p. 930 - 932 (2012)
Heterocyclic skeleton building blocks to afford dihydropyrimidinones and dihydropyridines based on neat adducts of diketene, alcohols and aldehydes via silica sulfuric acid (SSA) catalyzed ring opening of diketene in four-component Biginelli-type and Hant
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
SnCl4-functionalized nano-Fe3O4 encapsulated-silica particles as a novel heterogeneous solid acid for the synthesis of 1,4-dihydropyridine derivatives
Bamoniri, Abdolhamid,Fouladgar, Sara
, p. 78483 - 78490 (2015)
A novel type of green heterogeneous solid acid was prepared by the immobilization of SnCl4 on the surface of Fe3O4@SiO2 (Fe3O4@SiO2-SnCl4) and characterized by Fourier
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
N-Propyl-4-aza-1-azoniabicyclo[2.2.2]octane chloride-SBA-15 (SBA-DABCO) as basic mesoporous catalyst for the synthesis of 1,4-dihydropyridine hetrocyclic compounds
Kiasat, Ali Reza,Davarpanah, Jamal
, p. 179 - 182 (2015)
Regarding the green chemistry's goals, the development of mesoporous silica materials as attractive candidates in the search for supporting of catalysts is currently a subject of increasing interest. Therefore, in the present research n-propyl-4-aza-1-azo
