Amidation of carboxylic acids via the mixed carbonic carboxylic anhydrides and its application to synthesis of antidepressant (1 S ,2 R )-tranylcypromine

Ezawa, Tetsuya; Kawashima, Yuya; Noguchi, Takuya; Jung, Seunghee; Imai, Nobuyuki

doi:10.1016/j.tetasy.2017.10.015

Cited by 9 publications

(5 citation statements)

References 64 publications

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“…1 H-NMR was carried out to confirm the chemical structure of the synthesized cocrystal supporting the data from single crystal X-ray diffraction (SCD) analysis. The chemical structures of NIC and COU were confirmed by comparing the 1 H-NMR signals with previous researchers [63][64]. The 1 H-NMR signals of the NIC:COU (1:1) cocrystal are consistent with the signals of NIC and COU with a slight difference or no difference in terms of the chemical shift.…”

Section: Nuclear Magnetic Resonance (Nmr)supporting

confidence: 75%

Synthesis, Characterization and Morphological Study of Nicotinamide and <i>p</i>-Coumaric Acid Cocrystal

et al. 2020

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Cocrystallization is one of the potent methods used to modify the physicochemical properties of drugs. Cocrystal of nicotinamide (NIC):p-coumaric acid (COU) was synthesized by a slow evaporation method using acetonitrile. The cocrystals with different feed molar ratios (NIC:COU : 1:1, 1:2, and 2:1) were characterized using DSC, PXRD, and FTIR, which revealed the formation of different polymorphs for each feed molar ratio. A single crystal of the NIC:COU (1:1) cocrystal was analyzed using single crystal X-ray diffraction (SCD), and 1H-NMR revealed a greater cocrystal structure stability compared to the previously published cocrystal. The intermolecular hydrogen bonds, N-H···O, and O-H···O interactions played a major role in stabilizing the cocrystal structure. A molecular modeling technique was used for prediction and surface chemistry assessment of the morphology showed an elongated (along y-axis) octagonal crystal shape which was in a reasonable agreement with the experimental crystal morphology. The reduction in values of the cocrystal solubility in ethanol was supported by the DSC data and simulation of crystal facets where most the crystal facets exposed to polar functional groups. At the concentration of 31.3 µM, NIC:COU (1:1) cocrystal showed more effective DPPH scavenging with 77.06% increased activity compared to NIC at the same concentration.

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Section: Nuclear Magnetic Resonance (Nmr)supporting

confidence: 75%

Synthesis, Characterization and Morphological Study of Nicotinamide and <i>p</i>-Coumaric Acid Cocrystal

et al. 2020

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“…The ammonia and gaseous materials can be used to afford primary amides but harsh reaction conditions were usually necessary, such as high temperature and pressure. Classical synthetic methods are based on the amidation reaction of carbonyl compounds, such as carboxylic acids, acylchloride, anhydrides, alcohols or esters with amines (Scheme , a). However, significant drawbacks exist, such as low atom efficiency and the generation of large amounts of waste products.…”

Section: Introductionmentioning

confidence: 99%

An Efficient Protocol for the Synthesis of Primary Amides via Rh‐Catalyzed Rearrangement of Aldoximes

Song

et al. 2018

ChemistrySelect

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A system consisting of catalytic amounts of [Rh(CH 2 = CH 2 )Cl] 2 / PPh 2 Cy, and PhCl as the solvent efficiently catalyzes selective rearrangement of aldoximes to furnish various primary amides in moderate to good yields. Replacing the [Rh(CH 2 = CH 2 )Cl] 2 with Rh(NBD) 2 OTf enables the superior transformation to afford the amides with up to 99% yields. Attractive synthetic features associated with this methodology include absence of cocatalysts, broad functional group tolerance, good to excellent yields, low metal loadings, and operational convenience.[a] Dr.

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“…A series of amine were introduced to the ZnCl 2 electrolyte. These molecules show the characteristics of safety, [ 28 ] environmental‐benignity (precursors are ethanol, ammonia, and hydrogen chloride), inexpensiveness, high solubility [ 29 ] in water, and distinctive Lewis base strength difference. Compared with NH 4 Cl, the (ethyl‐, diethyl‐, triethyl‐) amine hydrochlorides show steady electron‐donating ability increment.…”

Section: Resultsmentioning

confidence: 99%

Cations Coordination‐Regulated Reversibility Enhancement for Aqueous Zn‐Ion Battery

Qian

Yao

et al. 2021

Adv Funct Materials

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Aqueous Zn‐ion batteries are emerging as a promising candidate for large‐scale energy storage, while the short lifetime and poor reversibility of Zn anodes limit their further development. When attempting to enhance reversibility, most reported methods involve toxic and pollutive substances and decreased water content, which inevitably sacrificed safety level, rate performance, and environmentally benign characteristics. Herein, a series of low‐cost and “green” molecules are introduced into the aqueous (ZnCl2, ZnSO4) electrolytes, featured with cations coordination capability, which can significantly inhibit the hydration step of Zn2+ and delay the formation of the key by‐products (Zn5(OH)8Cl2·H2O, 3Zn(OH)3·ZnSO4·5H2O) in aqueous electrolytes via regulating the coordination status of Zn2+. In the optimized electrolyte system, a highly reversible Zn metal anode presents excellent electrochemical performance, featured with a long lifespan over 1185 h at 1 mA cm−2 and smooth deposition morphology. Furthermore, Zn–MnO2 batteries based on the electrolyte deliver high capacity retention of 82.9% after 200 cycles. These breakthroughs suggest that this method offers a versatile toolbox toward developing future advanced multivalent metal batteries for large‐scale energy storage.

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Amidation of carboxylic acids via the mixed carbonic carboxylic anhydrides and its application to synthesis of antidepressant (1 S ,2 R )-tranylcypromine

Cited by 9 publications

References 64 publications

Synthesis, Characterization and Morphological Study of Nicotinamide and <i>p</i>-Coumaric Acid Cocrystal

Synthesis, Characterization and Morphological Study of Nicotinamide and <i>p</i>-Coumaric Acid Cocrystal

An Efficient Protocol for the Synthesis of Primary Amides via Rh‐Catalyzed Rearrangement of Aldoximes

Cations Coordination‐Regulated Reversibility Enhancement for Aqueous Zn‐Ion Battery

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