- Synthesis, cyrstal structure, fungicidal activity and molecular docking of nicotinic acyl urea derivatives
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A series of nicotinic acyl urea derivatives were designed using boscalid as a lead compound. They were synthesized via four steps. Their structures were confirmed by 1H NMR, HRMS and X-ray diffraction. Some of these new nicotinic acyl urea derivatives(4d, 4g, 4h and 4k) had moderate fungicidal activity against Gibberella zeae, Sclerotinia sclerotiorum, Rhizoctonia solani, Botrytis cinerea and Physalospora piricola at 50 mg/L, which is a little weaker than the commercial fungicide fluxapyroxad. The SAR was studied by using molecular docking.
- Zhang, Pei-Pei,Wang, Qiao,Min, Li-Jing,Wu, Hong-Ke,Weng, Jian-Quan,Tan, Cheng-Xia,Zhang, Yong-Gang,Liu, Xing-Hai
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- Mild and efficient conversion of nitriles to amides with basic urea- hydrogen peroxide adduct
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The urea-hydrogen peroxide adduct, an inexpensive, stable and easily handled reagent has shown utility for mild and efficient transformation of nitriles into the corresponding aliphatic or aromatic amides. Reaction proceeds in aqueous acetone, within 0.5-2. 5h, in the presence of catalytic amount of K2CO3, at room temperature.
- Balicki,Kaczmarek
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Read Online
- Regioselective synthesis of 2-chloro 3-pyridinecarboxylates
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2-Chlorocyanoacetate was found to undergo base-catalyzed Michael addition to α,β-unsaturated ketones or aldehydes to afford 5-oxopentenenitrile derivatives. In the presence of anhydrous HCl, these compounds cyclize to yield 2-chloro-3-pyridinecarboxylates. The process is highly regiospecific and useful in the synthesis of 2,3-disubstituted pyridines.
- Zhang,Stout,Keay,Scriven,Toomey,Goe
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- Visible-light-driven catalytic oxidation of aldehydes and alcohols to nitriles by 4-acetamido-tempo using ammonium carbamate as a nitrogen source
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A mild and efficient route to prepare nitriles from aldehydes by combining photoredox catalysis with oxoammonium cations is reported. The reaction is performed using ammonium carbamate as the nitrogen source. The practicality of the method is increased by the extension of the dual catalytic system to one-pot two-step conversion of alcohols to nitriles.
- Nandi, Jyoti,Leadbeater, Nicholas E.
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- Fluorine-containing nicotinyl urea compounds and preparation method and application thereof
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The invention discloses a fluorine-containing nicotinyl urea compound. The structural formula of the fluorine-containing nicotinyl urea compound is as shown in the specification. In a formula (I), H on a benzene ring is monosubstituted or polysubstituted by substituent groups R, wherein n is an integer from 1 to 5 and represents the number of the substituent groups R on the benzene ring; when n is1, H on the benzene ring is monosubstituted by the substituent group R; when n is from 2 to 5, H on the benzene ring is polysubstituted by the substituent groups R; and the substituent groups R on different substituent positions are same or different. The invention also provides a preparation method and application of the fluorine-containing nicotinyl urea compound. As a bactericide, the fluorine-containing nicotinyl urea compound is used for inhibiting botrytis cinerea, gibberella zeae, sclerotinia sclerotiorum or physalospora piricola.
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Paragraph 0040; 0046; 0049
(2019/02/21)
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- 2-chloro-N-(phenyl formamyl) nicotinamide compound, preparation method thereof and application of compound
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The invention discloses a 2-chloro-N-(phenyl formamyl) nicotinamide compound, a preparation method thereof and an application of the compound. The structural formula of the compound is as shown in a formula (I), H on a benzene ring is monosubstituted or polysubstituted by substituent groups R, n is an integer of 1-5 and indicates the number of the substituent groups R on the benzene ring, the H onthe benzene ring is monosubstituted by the substituent groups R when n=1, the H on the benzene ring is polysubstituted by the substituent groups R when n=2-5, the substituent groups R at different substituent positions are the same or different, and the substituent groups R are halogen, C1-C5 alkyl, C1-C5 alkoxy, phenoxy, nitryl, C1-C3 halogenated alkyl, C1-C3 halogenated alkoxy, phenyl or methoxycarbonyl. The compound is a novel compound with bactericidal activity and has a certain inhibiting effect on cucumber botrytis cinerea, sclerotinia sclerotiorum, fusarium graminearum and physalosporapiricola.
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Paragraph 0030; 0033
(2019/04/06)
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- Synthesis, crystal structure, fungicidal activity, molecular docking, and density functional theory study of 2-chloro-N-(p-tolylcarbamoyl)nicotinamide
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A new nicotine acylurea, 2-chloro-N-(p-tolylcarbamoyl)nicotinamide (4) was synthesized and its structure was confirmed by proton nuclear magnetic resonance, high resolution mass spectrometry analyses, and X-ray diffraction. The preliminary activity results demonstrated that the compound 4 exhibits moderate inhibitory activity against Sclerotinia sclerotiorum and Physalospora piricola. Further, docking results indicated that the key active group is amide group and pyridine moiety. The density functional theory calculation results showed that direct of electron transfer is from benzene ring to pyridine ring. The energy gap between the highest occupied molecular orbital and lowest unoccupied molecular orbital was calculated.
- Chen, Wei-Ting,Wang, Qiao,Min, Li-Jing,Wu, Hong-Ke,Weng, Jian-Quan,Tan, Cheng-Xia,Zhang, Yong-Gang,Hu, Bei-Zhen,Liu, Xing-Hai
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p. 429 - 435
(2020/01/03)
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- Nitrile Hydration Reaction Using Copper Iodide/Cesium Carbonate/DBU in Nitromethane-Water
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The catalytic nitrile hydration (amide formation) in a copper iodide/cesium carbonate/1,8-diazabicyclo[5.4.0]undec-7-ene/nitromethane-water system is described. The protocol is robust and reliable; it can be applied to a broad range of substrates with high chemoselectivity.
- Kuwabara, Jun,Sawada, Yoshiharu,Yoshimatsu, Mitsuhiro
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supporting information
p. 2061 - 2065
(2018/09/14)
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- A synthesis method of midanping
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The invention discloses a method for synthesizing mirtazapine. According to the method, 2-halogenated nicotinonitrile is used as an initial compound, and 2-chloronicotinamide, 2-(4-methyl-2phenyl-1-piperazinyl)nicotinamide, 2-(4-methyl-2phenyl-1-piperazinyl)nicotinic acid, 1-(3-hydroxymethylpyridyl-2-)-4-methyl-2-phenylpiperazine and other intermediate products are sequentially synthesized to prepare the mirtazapine. Against the defects in a current mirtazapine synthesizing method, the process is improved, a new synthesizing route is designed, and a preparation method which is economical and is easy for practical operation is provided to mirtazapine synthesis. The method is suitable for large-scale industrial production.
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Paragraph 0014; 0037; 0038
(2017/12/27)
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- 3H-1,2,4-Dithiazol-3-one compounds as novel potential affordable antitubercular agents
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Small molecules with oxathiazol-2-one moiety were recently reported as potent inhibitors of Mycobacterium bovis var. bacilli Calmette-Guérin (BCG), among which HT1171 was the most potent and selective proteasome inhibitor. Herein we synthesized a series of novel compounds by bioisosteric replacement of the oxathiazol-2-one ring with 3H-1,2,4-dithiazol-3-one, and also fifteen 1,3,4-oxathiazol-2-one molecules in order for potency comparison and structure-activity relationship elucidation since their antibacterial effects on the virulent strains were not evaluated before. All the compounds were assessed for antitubercular activities on the virulent H37Rv strain by a serial dilution method. Among the tested compounds, 3H-1,2,4-dithiazol-3-one compound 4n was found to be the most active with a lowest MIC90 value of 1 μg/mL. Furthermore, the cytotoxicities of all the compounds against normal human liver cell line L02 were determined by an MTT method. Compound 4n displayed a lower inhibitory ratio than HT1171 at the concentration of 100 μM, indicating its better safety profile.
- Yang, Jianzhong,Pi, Weiyi,Xiong, Li,Ang, Wei,Yang, Tao,He, Jun,Liu, Yuanyuan,Chang, Ying,Ye, Weiwei,Wang, Zhenling,Luo, Youfu,Wei, Yuquan
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supporting information
p. 1424 - 1427
(2013/03/14)
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- Synthesis, characterization, structures and antioxidant activity of nicotinoyl based organoselenium compounds
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A series of nicotinoyl based organoselenium compounds, [2-NC 5H3(3-COOH)Se]2 (1), [2-NC5H 3(3-CO)Se-Se] (2), [2-NC5H3(3-CONH 2)Se]2 (3), [2-NC5H3(3-CONHPh)Se] 2 (4), [2-NC5H3(3-CONHpyrimidine)Se] 2 (5), [2-NC5H3(3-CONHPh)SeBr] (6) and [2-NC5H3(3-CONHPh)SeI] (7) have been synthesized and characterized by absorption, IR, NMR (1H, 13C{ 1H}, 77Se{1H}) and mass spectrometry. The crystal structures of [2-NC5H3(3-CO)Se-Se] (2) and [2-NC5H3(3-CONHPh)Se]2 (4) have been determined. The structure of (4) revealed the existence of two intra-molecular Se?X (X = O and N) interactions, as a result of this, C-Se-Se-C torsion angle is unusually large (180°). The GPx mimicking activity of these compounds has been evaluated using methods based on 1H NMR spectroscopy and HPLC. Free radical scavenging ability of the compounds was examined by DPPH and deoxyribose assay. All these studies indicated that the compound (3) not only showed highest GPx activity but also has a very good free radical scavenging ability thus making it a novel structure for development of nicotine based antioxidants.
- Parashiva Prabhu,Phadnis, Prasad P.,Wadawale, Amey P.,Indira Priyadarsini,Jain, Vimal K.
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scheme or table
p. 42 - 50
(2012/09/05)
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- Copper(II)-catalyzed hydration of nitriles with the aid of acetaldoxime
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An efficient method for the selective hydration of nitrile to amide by employing inexpensive copper salt catalyst and commercially available acetaldoxime in environmentally friendly water is described. Under this protocol, nitriles including aromatic nitriles, heterocyclic nitriles and aliphatic nitriles were converted into the corresponding amides in good to excellent yields.
- Ma, Xiao-Yun,He, Ying,Hu, Yu-Lin,Lu, Ming
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supporting information; experimental part
p. 449 - 452
(2012/02/01)
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- An improved method for the conversion of nitriles to amides using N,N-disubstituted hydroxylamine
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An improved method for the selective hydration of nitriles to amides employing N,N-disubstituted hydroxylamine is described leading to a reduction in reaction time and improved yield. Amides having electron-donating groups, which were not reported using the original method, were obtained in excellent yields. The amount of N,N-disubstituted hydroxylamine was reduced from three equivalents to one equivalent and the use of water as the reaction medium is environmentally friendly.
- Ma, Xiao-Yun,Lu, Ming
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experimental part
p. 480 - 483
(2011/10/18)
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- HYDROXYAPATITE WITH SILVER SUPPORTED ON THE SURFACE THEREOF
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An object of the present invention is to provide a hydroxyapatite with silver supported on the surface thereof, a new compound useful as a catalyst for the reaction of producing an amide compound by hydration of the corresponding nitrile compound. The hydroxyapatite with silver supported on the surface thereof according to the present invention is obtained by supporting zero-valent Ag on the surface of a hydroxyapatite. Also provided are a hydroxyapatite with silver supported on the surface thereof used as a catalyst, and a method for producing an amide compound, comprising producing the amide compound by hydration of the corresponding nitrile compound in the presence of a hydroxyapatite with silver supported on the surface thereof having zero-valent Ag supported on the surface of the hydroxyapatite.
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Page/Page column 5; 6
(2011/01/11)
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- Ceric ammonium nitrate (CAN) promoted efficient solid phase synthesis of amide derivatives: A green approach
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Ceric ammonium nitrate (CAN) has been found to be an efficient catalyst for the solid phase synthesis of amide derivatives of a wide range of substituted carboxylic acids and urea in excellent yields under microwave irradiation conditions. High yields are achieved even on a gram scale, while reaction times are considerably shortened. This method displays both economic and environmental advantages.
- Reddy, Ch. Sanjeeva,Raghu,Nagaraj
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p. 315 - 318
(2008/09/20)
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- Processes for producing 2-Halo-nicotinic acid derivatives and precursors thereto
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Disclosed are preferred processes for the preparation of 2-halo-nicotinic acid derivatives of formula (IV): STR1 by cyclocondensation of a 4-halo-4-cyanocarbonyl compound of formula (III): STR2 wherein X is Cl or Br; Y is a carbonyl group and R1, R2 and R3 are each, independently, H, Cl, Br or an organic radical. Further preferred aspects include the preparation of the above-noted 4-halo-4-cyanocarbonyl compound via Michael addition of a 2-halonitrile with an α,β-unsaturated aldehyde or ketone, and the preparation of the 2-halonitrile by redistribution of halogen between a 2,2-dihalonitrile and a parent nitrile.
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- A MILD EFFICIENT PROCEDURE FOR THE CONVERSION OF CARBOXYLIC ACID ESTERS TO PRIMARY AMIDES USING FORMAMIDE/METHANOLIC SODIUM METHOXIDE
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An improved method for the preparation of primary carboxylic acid amides from the corresponding esters is described.This reaction was easily followed by GLC and was usually complete in less than one hour.
- Jagdmann, G. Erik,Munson, H. Randall,Gero, Thomas W.
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p. 1203 - 1208
(2007/10/02)
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