6320-63-4Relevant articles and documents
N -Alkylation of organonitrogen compounds catalyzed by methylene-linked bis-NHC half-sandwich ruthenium complexes
Botubol-Ares, José Manuel,Collado, Isidro G.,Jiménez-Tenorio, Manuel,Moutaoukil, Zakaria,Serrano-Díez, Emmanuel
supporting information, p. 831 - 839 (2022/02/03)
An efficient ruthenium-catalyzed N-alkylation of amines, amides and sulfonamides has been developed employing novel pentamethylcyclopentadienylruthenium(ii) complexes bearing the methylene linked bis(NHC) ligand bis(3-methylimidazol-2-ylidene)methane. The
AMINE-BORANES AS BIFUNCTIONAL REAGENTS FOR DIRECT AMIDATION OF CARBOXYLIC ACIDS
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Paragraph 0008-0009; 0063-0064, (2022/03/04)
The present invention generally relates to a process for selective and direct activation and subsequent amidation of aliphatic and aromatic carboxylic acids to afford an amide R3CONR1R2. That the process is capable of delivering gaseous or low-boiling point amines provides a major advantage over existing methodologies, which involves an intermediate of triacyloxyborane-amine complex [(R3CO2)3—B—NHR1R2]. This procedure readily produces primary, secondary, and tertiary amides, and is compatible with the chirality of the acid and amine involved. The preparation of known pharmaceutical molecules and intermediates has also been demonstrated.
CuO-decorated magnetite-reduced graphene oxide: a robust and promising heterogeneous catalyst for the oxidative amidation of methylarenes in waterviabenzylic sp3C-H activation
Ebrahimi, Edris,Khalafi-Nezhad, Ali,Khalili, Dariush,Rousta, Marzieh
, p. 20007 - 20020 (2021/11/12)
A magnetite-reduced graphene oxide-supported CuO nanocomposite (rGO/Fe3O4-CuO) was preparedviaa facile chemical method and characterized by Fourier-transform infrared spectroscopy (FTIR), X-ray diffraction (XRD), UV-vis spectroscopy, scanning electron microscopy (SEM), transmission electron microscopy (TEM), energy dispersive spectroscopy (EDS), Brunauer-Emmett-Teller (BET) analysis, vibrating-sample magnetometry (VSM), and thermogravimetric (TG) analysis. The catalytic activity of the rGO/Fe3O4-CuO nanocomposite was probed in the direct oxidative amidation reaction of methylarenes with free amines. Various aromatic and aliphatic amides were prepared efficiently at room temperature from cheap raw chemicals usingtert-butyl hydroperoxide (TBHP) as a “green” oxidant and low-toxicity TBAI in water. This method combines the oxidation of methylarenes and amide bond formation into a single operation. Moreover, the synthesized nanocomposites can be separated from the reaction mixtures using an external magnet and reused in six consecutive runs without a noticeable decrease in the catalytic activity.
Amine-boranes as Dual-Purpose Reagents for Direct Amidation of Carboxylic Acids
Choudhary, Shivani,Hamann, Henry J.,Ramachandran, P. Veeraraghavan
, (2020/11/13)
Amine-boranes serve as dual-purpose reagents for direct amidation, activating aliphatic and aromatic carboxylic acids and, subsequently, delivering amines to provide the corresponding amides in up to 99% yields. Delivery of gaseous or low-boiling amines as their borane complexes provides a major advantage over existing methodologies. Utilizing amine-boranes containing borane incompatible functionalities allows for the preparation of functionalized amides. An intermolecular mechanism proceeding through a triacyloxyborane-amine complex is proposed.
Discovery and synthesis of 6,7,8,9-tetrahydro-5H-pyrido[4,3-c]azepin-5-one-based novel chemotype CCR2 antagonists via scaffold hopping strategy
Qin, Li-Huai,Wang, Zhi-Long,Xie, Xin,Long, Ya-Qiu
, p. 3559 - 3572 (2018/05/28)
The chemokine CC receptor subtype 2 (CCR2) has attracted intensive interest for drug development in diverse therapeutic areas, including chronic inflammatory diseases, diabetes, neuropathic pain, atherogenesis and cancer. By employing a cut-and-sew scaffold hopping strategy, we identified an active scaffold of 3,4-dihydro-2,6-naphthyridin-1(2H)-one as the central pharmacophore to derive novel CCR2 antagonists. Systematic structure–activity relationship study with respect to the ring size and the substitution on the naphthyridinone ring gave birth to 1-arylamino-6-alkylheterocycle-6,7,8,9-tetrahydro-5H-pyrido[4,3-c]azepin-5-ones as a brand new chemotype of CCR2 antagonists with nanomolar inhibitory activity. The best antagonism activity in this series was exemplified by compound 13a, which combined the optimal substitutions of 3,4-dichlorophenylamino at C-1 and 3-(4-(N-methylmethylsulfonamido)piperidin-1-yl)propyl at N-6 position, leading to an IC50 value of 61 nM and 10-fold selectivity for CCR2 over CCR5. Efficient and general synthesis was established to construct the innovative core structure and derive the compound collections. This is the first report on our designed 6,7,8,9-tetrahydro-5H-pyrido[4,3-c]azepin-5-one as novel CCR2 antagonist scaffold and its synthesis.
Synthesis of acyl fluorides via photocatalytic fluorination of aldehydic C-H bonds
Meanwell, Michael,Lehmann, Johannes,Eichenberger, Marc,Martin, Rainer E.,Britton, Robert
, p. 9985 - 9988 (2018/09/11)
Acyl fluorides are versatile acylating agents owing to their unique stability. Their synthesis, however, can present challenges and is typically accomplished through deoxyfluorination of carboxylic acids. Here, we demonstrate that acyl fluorides can be prepared directly from aldehydes via a C(sp2)-H fluorination reaction involving the inexpensive photocatalyst sodium decatungstate and electrophilic fluorinating agent N-fluorobenzenesulfonimide. This convenient fluorination strategy enables direct conversion of aliphatic and aromatic aldehydes into acylating agents.
A rare earth/sodium heteroatoms double-metal complex and its preparation and use
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Paragraph 0061; 0062, (2017/11/16)
The invention discloses a rare earth/sodium heterobimetallic complex as well as a preparation method and application thereof. The molecular formula of the rare earth/sodium heterobimetallic complex is Ln2Na8(OCH2CF3)14(THF)6, wherein Ln represents rare earth metal. The rare earth/sodium heterobimetallic complex disclosed by the invention can be applied to catalysis of the amide exchange reaction to synthesize an amide compound, the reaction conditions are mild, the catalyst dosage is relatively small, and the substrate application range is relatively wide.
An Efficient Heterobimetallic Lanthanide Alkoxide Catalyst for Transamidation of Amides under Solvent-Free Conditions
Sheng, Hongting,Zeng, Ruijie,Wang, Wenjuan,Luo, Shuwen,Feng, Yan,Liu, Jing,Chen, Weijian,Zhu, Manzhou,Guo, Qingxiang
, p. 302 - 313 (2017/02/05)
A practical heterobimetallic lanthanide-catalyzed transamidation of primary, secondary and tertiary amides with aliphatic and aromatic amines has been developed. The methodology was also applied to the weakly reactive thioamides to demonstrate its versatility and wide substrate scope. The heterobimetallic lanthanide catalysts showed high catalytic activity and a wide scope of substrates with good to excellent yields under solvent-free conditions. Efficient activation of the transamidation can be realized by the above complexes acting as cooperative acid–base bifunctional catalysts, which are proposed to be responsible for the higher reactivity in comparison with simple monometallic catalysts. (Figure presented.).
Clean synthesis of primary to tertiary carboxamides by CsOH-catalyzed aminolysis of nitriles in water
Li, Yang,Chen, Haonan,Liu, Jianping,Wan, Xujun,Xu, Qing
supporting information, p. 4865 - 4870 (2016/10/06)
Using CsOH as the only catalyst and utilizing its "cesium effect", a clean synthesis of a wide range of primary, secondary, and tertiary carboxamides was achieved by aminolysis reactions of nitriles with ammonia, primary, or secondary amines in water. Studies on the control reactions revealed that the reactions with ammonia most probably proceed via an aminolysis path by the initial addition of ammonia to Cs-activated nitriles to form unsubstituted amidine intermediates, while the reactions with primary or secondary amines may proceed via a hydration/transamidation path by the initial hydration of the Cs-activated nitriles to form primary carboxamide intermediates followed by their transamidation with amines through the formation of substituted amidine intermediates.
C-N Coupling of Amides with Alcohols Catalyzed by N-Heterocyclic Carbene-Phosphine Iridium Complexes
Kerdphon, Sutthichat,Quan, Xu,Parihar, Vijay Singh,Andersson, Pher G.
, p. 11529 - 11537 (2015/12/04)
N-Heterocyclic carbene-phosphine iridium complexes (NHC-Ir) were developed/found to be a highly reactive catalyst for N-monoalkylation of amides with alcohols via hydrogen transfer. The reaction produced the desired product in high isolated yields using a wide range of substrates with low catalyst loading and short reaction times.
