132-75-2Relevant articles and documents
Mechanistic Insight Facilitates Discovery of a Mild and Efficient Copper-Catalyzed Dehydration of Primary Amides to Nitriles Using Hydrosilanes
Liu, Richard Y.,Bae, Minwoo,Buchwald, Stephen L.
, p. 1627 - 1631 (2018)
Metal-catalyzed silylative dehydration of primary amides is an economical approach to the synthesis of nitriles. We report a copper-hydride(CuH)-catalyzed process that avoids a typically challenging 1,2-siloxane elimination step, thereby dramatically increasing the rate of the overall transformation relative to alternative metal-catalyzed systems. This new reaction proceeds at ambient temperature, tolerates a variety of metal-, acid-, or base-sensitive functional groups, and can be performed using a simple ligand, inexpensive siloxanes, and low catalyst loading.
Synthesis, characterisation, optical properties and theoretical calculations of a new fluorescent heterocyclic system: 3H-benzo[a]pyrazolo[3,4-j]acridine
Alipoor, Hamideh,Pordel, Mehdi,Morsali, Ali
, p. 371 - 375 (2017)
Four new fluorescent dyes derived from the 3H-benzo[a]pyrazolo[3,4-j]acridine system were synthesised and fully characterised by 1H NMR, 13C NMR, mass and analytical data. These new fluorophores were prepared from the reaction of 1-alkyl-5-nitro-1H-indazoles with 1-naphthylacetonitrile via nucleophilic substitution of hydrogen, in high yields. The optical properties of the dyes were also investigated and the results revealed that, in some cases, they have higher quantum yields compared with well-known fluorescent dyes such as fluorescein. Solvent effects on the fluorescence characteristics of the four compounds indicated that the emission wavelength is red-shifted with increasing solvent polarity. Furthermore, density functional theory calculations using the B3LYP hybrid functional and the 6-311++G(d,p) basis set provided the optimised geometries and relevant frontier orbitals of the compounds. Calculated electronic absorption spectra were also obtained using the time-dependent density functional theory method.
Straightforward conversion of alcohols into nitriles
Tarrade-Matha, Aurelie,Pillon, Florence,Doris, Eric
, p. 1646 - 1649 (2010)
The reaction of various alcohols with cyanogen bromide, triphenylphosphine, and a base afforded the corresponding nitrile in satisfactory yields. Copyright
Mild and reversible dehydration of primary amides with PdCl2 in aqueous acetonitrile
Maffioli, Sonia I.,Marzorati, Ettore,Marazzi, Alessandra
, p. 5237 - 5239 (2005)
(Chemical Equation Presented) A new, mild, and reversible method to convert primary amides to nitriles in good yields using PdCl2 in aqueous acetonitrile is described.
Preparation method of naphthalene ring C marked α .
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, (2021/10/05)
The invention discloses C labeled α - naphthalene acetic acid preparation method and belongs to the field of radioisotope C labeled compounds. C-labeled α - naphthylacetic acid preparation method, C radioisotope labeling is introduced on a naphthalene ring structure α -naphthol acid, C labeling site is in α-position. The method has the advantages that the reaction raw materials are easily available, the synthesis steps are high in yield, the total yield is more 60%, C marker isotopes are less in use amount, and waste is generated. The marker site α-position on the naphthalene ring is less likely to be metabolized compared to C-labeled branched acetic acid, and the synthesized C-labeled compound provides a better study of α -naphthoic acid in the environment.
Facile dehydration of primary amides to nitriles catalyzed by lead salts: The anionic ligand matters
Ruan, Shixiang,Ruan, Jiancheng,Chen, Xinzhi,Zhou, Shaodong
, (2020/12/09)
The synthesis of nitrile under mild conditions was achieved via dehydration of primary amide using lead salts as catalyst. The reaction processes were intensified by not only adding surfactant but also continuously removing the only by-product, water from the system. Both aliphatic and aromatic nitriles can be prepared in this manner with moderate to excellent yields. The reaction mechanisms were obtained with high-level quantum chemical calculations, and the crucial role the anionic ligand plays in the transformations were revealed.
Method for dehydrating primary amide into nitriles under catalysis of cobalt
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Paragraph 0078-0080, (2021/06/21)
The invention provides a method for dehydrating primary amide into nitrile. The method comprises the following steps: mixing primary amide (II), silane, sodium triethylborohydride, aminopyridine imine tridentate nitrogen ligand cobalt complex (I) and a reaction solvent under the protection of inert gas, carrying out reacting at 60-100 DEG C for 6-24 hours, and post-treating reaction liquid to obtain a nitrile compound (III). According to the invention, an effective method for preparing nitrile compounds by cobalt-catalyzed primary amide dehydration reaction by using the novel aminopyridine imine tridentate nitrogen ligand cobalt complex catalyst is provided; and compared with existing methods, the method has the advantages of simple operation, mild reaction conditions, wide application range of reaction substrates, high selectivity, stable catalyst, high efficiency, and relatively high practical application value in synthesis.
Assembly of α-(Hetero)aryl Nitriles via Copper-Catalyzed Coupling Reactions with (Hetero)aryl Chlorides and Bromides
Chen, Ying,Xu, Lanting,Jiang, Yongwen,Ma, Dawei
supporting information, p. 7082 - 7086 (2021/02/26)
α-(Hetero)aryl nitriles are important structural motifs for pharmaceutical design. The known methods for direct synthesis of these compounds via coupling with (hetero)aryl halides suffer from narrow reaction scope. Herein, we report that the combination of copper salts and oxalic diamides enables the coupling of a variety of (hetero)aryl halides (Cl, Br) and ethyl cyanoacetate under mild conditions, affording α-(hetero)arylacetonitriles via one-pot decarboxylation. Additionally, the CuBr/oxalic diamide catalyzed coupling of (hetero)aryl bromides with α-alkyl-substituted ethyl cyanoacetates proceeds smoothly at 60 °C, leading to the formation of α-alkyl (hetero)arylacetonitriles after decarboxylation. The method features a general substrate scope and is compatible with various functionalities and heteroaryls.
Naphthylacetic acid preparation method
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Paragraph 0037; 0039; 0040; 0047; 0049; 0050; 0057; 0059, (2020/03/12)
The invention discloses a naphthylacetic acid preparation method, which comprises: naphthylacetic acid is prepared by using 1-chloromethylnaphthalene as a starting raw material, using cuprous iodide as a catalyst, using potassium ferrocyanide as a cyanide source and adding triethyl benzyl ammonium chloride as a phase transfer catalyst into a reaction system. According to the invention, traditionalpotassium cyanide or sodium cyanide is replaced with potassium ferrocyanide as the cyanide source, so the safety threat of potassium cyanide or sodium cyanide to operators in a production process isavoided, and environment pollution caused by highly toxic substances is reduced; and the preparation method has advantages of simple post-treatment, low energy consumption and few three-waste.
One-pot method for the synthesis of 1-aryl-2-aminoalkanol derivatives from the corresponding amides or nitriles
Bobal, Pavel,Otevrel, Jan,Svestka, David
, p. 25029 - 25045 (2020/07/14)
We have identified a novel one-pot method for the synthesis of β-amino alcohols, which is based on C-H bond hydroxylation at the benzylic α-carbon atom with a subsequent nitrile or amide functional group reduction. This cascade process uses molecular oxygen as an oxidant and sodium bis(2-methoxyethoxy)aluminum hydride as a reductant. The substrate scope was examined on 30 entries and, although the respective products were provided in moderate yields only, the above simple protocol may serve as a direct and powerful entry to the sterically congested 1,2-amino alcohols that are difficult to prepare by other routes. The plausible mechanistic rationale for the observed results is given and the reaction was applied to a synthesis of a potentially bioactive target. This journal is
