- 1,1-Difluoro-3-aryl(heteroaryl)-1: H -pyrido[1,2- c] [1,3,5,2]oxadiazaborinin-9-ium-1-uides: Synthesis; Structure; and photophysical, electrochemical, and BSA-binding studies
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This paper presents a series of six examples of 1,1-difluoro-3-aryl(heteroaryl)-1H-pyrido[1,2-c][1,3,5,2]oxadiazaborinin-9-ium-1-uides (2) - in which aryl(heteroaryl) = phenyl, 4-MeC6H4, 4-N(CH3)2C6H
- Bonacorso, Helio G.,Calheiro, Tainara P.,Iglesias, Bernardo A.,Acunha, Thiago V.,Franceschini, Steffany Z.,Ketzer, Alex,Meyer, Alexandre R.,Rodrigues, Letícia V.,Nogara, Pablo A.,Rocha, Jo?o B. T.,Zanatta, Nilo,Martins, Marcos A. P.
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- Singlet oxygen mediated one pot synthesis of N-pyridinylamides via oxidative amidation of aryl alkyl ketones
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An environmental friendly, efficient protocol has been realized for the synthesis of N-pyridinylamides via copper catalyzed oxidative amidation of aryl alkyl ketones with 2-aminopyridines. This one pot protocol involves chemo selective cleavage of C (O)–C bond in the presence of singlet oxygen. The reaction conditions are simple, tolerates wide range of substrates and the products were formed in good to excellent yields. This method offers a moderate improvement over the earlier successful attempts in generating N-pyridinylamides.
- Sofi, Firdoos Ahmad,Sharma, Rohit,Kavyasree,Salim, Sumi Aisha,Wanjari, Pravin J.,Bharatam, Prasad V.
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- Copper(I)-catalysed aerobic oxidative selective cleavage of C[sbnd]C bond with DMAP: Facile access to N-substituted benzamides
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A base/DMAP system for efficient oxidative cleavage of C(CO)–C(alkyl) bond to generate N-substituted benzamides has been developed in the presence of copper(I) chloride. The usage of inexpensive copper catalyst, broad substrate scope, mild conditions make
- Ma, Haojie,Lu, Guoqiang,Han, Bo,Huang, Guosheng,Zhang, Yuqi,Wang, Ji-Jiang
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- CuI incorporated cobalt ferrite nanoparticles as a magnetically separable catalyst for oxidative amidation reaction
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A Cu-incorporated magnetic nanocatalyst (CoFe2O4?SiO2-SH-CuI) has been developed by immobilizing CuI on the modified surface of CoFe2O4 magnetic nanoparticles. The surface of the silica coated cobalt
- Dutta, Mintu Maan,Talukdar, Hrishikesh,Phukan, Prodeep
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- N-pyridinylbenzamides: an isosteric approach towards new antimycobacterial compounds
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A series of N-pyridinylbenzamides was designed and prepared to investigate the influence of isosterism and positional isomerism on antimycobacterial activity. Comparison to previously published isosteric N-pyrazinylbenzamides was made as an attempt to draw structure–activity relationships in such type of compounds. In total, we prepared 44 different compounds, out of which fourteen had minimum inhibitory concentration (MIC) values against Mycobacterium tuberculosis H37Ra below 31.25?μg/ml, most promising being N-(5-chloropyridin-2-yl)-3-(trifluoromethyl)benzamide (23) and N-(6-chloropyridin-2-yl)-3-(trifluoromethyl)benzamide (24) with MIC?=?7.81?μg/ml (26?μm). Five compounds showed broad-spectrum antimycobacterial activity against M. tuberculosis H37Ra, M. smegmatis and M. aurum. N-(pyridin-2-yl)benzamides were generally more active than N-(pyridin-3-yl)benzamides, indicating that N-1 in the parental structure of N-pyrazinylbenzamides might be more important for antimycobacterial activity than N-4. Marginal antibacterial and antifungal activity was observed for title compounds. The hepatotoxicity of title compounds was assessed in vitro on hepatocellular carcinoma cell line HepG2, and they may be considered non-toxic (22 compounds with IC50 over 200?μm).
- Nawrot, Daria,Suchánková, Eli?ka,Jan?ourek, Ond?ej,Kone?ná, Klára,Bárta, Pavel,Dole?al, Martin,Zitko, Jan
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p. 686 - 700
(2020/11/30)
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- Traceless selenocarboxylates for the one-pot synthesis of amides and derivatives
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We have recently reported a one-pot procedure for glycosyl amides synthesis using selenocarboxylate as traceless reagent. Herein, we present a further application of selenocarboxylate-azide reaction for amide bond formation on a broader range of substrates, including heterocyclic systems and fatty acid. This method proved to be highly efficient for the synthesis of primary and secondary amides, sulfonamides, imides, phosphoramide and also carbamate.
- Silva, Luana,Rosário, Alisson R.,Machado, Bianca M.,Lüdtke, Diogo S.
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supporting information
(2020/12/25)
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- Cu-catalyzed cross-coupling of methyl ketones and pyridin-2-amines for the synthesis of N-(2-pyridyl)-α-ketoamides
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An efficient copper-catalyzed strategy for the synthesis of α-ketoamides via cross-coupling of methyl ketones and pyridin-2-amines is described. This transformation has provided a simple process for the formation of C?N and C=O bonds to prepare α-ketoamid
- Chen, Ali,Guo, Pengfeng,Lin, Haoming,Liu, Xiang,Rao, Chuixiong,Yang, Daji,Yu, Yue
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p. 417 - 421
(2020/11/30)
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- Singlet oxygen mediated dual C-C and C-N bond cleavage in visible light
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A tandem cleavage of carbon-carbon and carbon-nitrogen bonds in imidazo[1,2-a]pyridines and imidazo[1,2-a]quinolines is reported in the presence of eosin Y and visible light. The ring opening occurs under ambient conditions through singlet oxygen insertio
- Jain, Nidhi,Kumar, Sharvan,Ritu,Sharma, Charu
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p. 2921 - 2928
(2020/04/28)
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- Direct Transformation of Alkylarenes into N-(Pyridine-2-yl)amides by C(sp3)–C(sp3) Bond Cleavage
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C(sp3)–H bond functionalization and C(sp3)–C(sp3) bond cleavage are very challenging transformations in chemistry. Herein, we report a mild and green methodology for the construction of N-(pyridine-2-yl)amides via tandem C(sp3)–H activation/C–C bond cleavage of alkylarenes. Various N-heterocyclic amides were directly synthesized from alkylarenes in water in moderate to good yields.
- Zhou, Haipin,Liu, Yanpeng,Xia, Haidong,Xu, Jinyi,Wang, Tingfang,Xu, Shengtao
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p. 6468 - 6473
(2020/10/02)
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- Copper Catalyzed Oxidative C-C Bond Cleavage of 1,2-Diketones: A Divergent Approach to 1,8-Naphthalimides, Biphenyl-2,2′-dicarboxamides, and N-Heterocyclic Amides
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We report here a simple and efficient copper catalyzed oxidative C-C bond cleavage of stable aromatic cyclic-fused and acyclic 1,2-diketones to deliver amides and imides in high yields. This newly developed protocol provides an excellent tool to transform structurally different 1,2-diketones into different products under the same reaction conditions. The key synthetic features of this methodology are the formation of 1,8-naphthalimides and biphenyl-2,2′-dicarboxamide motifs in high yields. The fluorescent studies of 1,8-naphthalimide derivatives were also carried out in order to show the potential application of these scaffolds.
- Sakhare, Priyanka R.,Subramanian, Parthasarathi,Kaliappan, Krishna P.
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p. 2112 - 2125
(2019/02/14)
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- Multicomponent Synthesis of Isoindolinones by RhIII Relay Catalysis: Synthesis of Pagoclone and Pazinaclone from Benzaldehyde
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A practical one-pot isoindolinone synthesis enabled by RhIII catalysis was developed. The advantage of this protocol is that it does not require pre-preparation of amide substrates, because RhIII participates in two reactions independently. This mild, operationally multicomponent process transforms a wide variety of commercially available aldehydes into the corresponding γ-lactams in good yields, thereby demonstrating that N-pyridin-2-yl benzamide is an effective directing group. Notably, the anxiolytic drugs pagoclone and pazinaclone can be directly prepared by this methodology.
- Zhang, Yan,Zhu, Haiqian,Huang, Yuting,Hu, Qi,He, Yu,Wen, Yihang,Zhu, Gangguo
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supporting information
p. 1273 - 1277
(2019/02/26)
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- Chemodivergent synthesis of: N -(pyridin-2-yl)amides and 3-bromoimidazo[1,2- a] pyridines from α-bromoketones and 2-aminopyridines
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N-(Pyridin-2-yl)amides and 3-bromoimidazo[1,2-a]pyridines were synthesized respectively from α-bromoketones and 2-aminopyridine under different reaction conditions. N-(Pyridin-2-yl)amides were formed in toluene via C-C bond cleavage promoted by I2/s
- Liu, Yanpeng,Lu, Lixue,Zhou, Haipin,Xu, Feijie,Ma, Cong,Huang, Zhangjian,Xu, Jinyi,Xu, Shengtao
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p. 34671 - 34676
(2019/11/13)
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- Diverse Oxidative C(sp2)-N Bond Cleavages of Aromatic Fused Imidazoles for Synthesis of α-Ketoamides and N-(pyridin-2-yl)arylamides
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An efficient and chemoselective C(sp2)-N bond cleavage of aromatic imidazo[1,2-a]pyridine molecules is developed. A broad scope of amide compounds such as α-ketoamides and N-(pyridin-2-yl)arylamides are afforded as the final products in up to quantitative yields. Diverse C-N bond cleavages are controlled by the oxidative species used in this transformation, with various amide products afforded in a chemoselective fashion. A preliminary study indicated that some α-ketoamides exhibit anti-Tobacco Mosaic Virus activity for potential use in plant protection.
- Xu, Fangzhou,Wang, Yanyan,Xun, Xiwei,Huang, Yun,Jin, Zhichao,Song, Baoan,Wu, Jian
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p. 8411 - 8422
(2019/05/17)
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- Synthesis method of N-heterocyclic acylamide derivative
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The invention discloses a synthesis method of an N-heterocyclic acylamide derivative. A reaction general formula is as shown in the specification. According to the synthesis method, an imidazo heterocyclic amine compound I is taken as a raw material; unde
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Paragraph 0048; 0049; 0050
(2019/01/14)
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- Metal-Free Synthesis of N-(Pyridine-2-yl)amides from Ketones via Selective Oxidative Cleavage of C(O)-C(Alkyl) Bond in Water
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The TBHP/TBAI-mediated synthesis of N-(pyridine-2-yl)amides in water from ketones and 2-aminopyridine via direct oxidative C-C bond cleavage has been developed. A series of ketones, including more challenging inactive aromatic ketones substituted with div
- Liu, Yanpeng,Sun, Honghao,Huang, Zhangjian,Ma, Cong,Lin, Aijun,Yao, Hequan,Xu, Jinyi,Xu, Shengtao
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p. 14307 - 14313
(2019/01/03)
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- Copper(II)-mediated, carbon degradation-based amidation of phenylacetic acids toward N -substituted benzamides
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The unprecedented synthesis of N-aryl substituted benzamides via the assembly of primary amines and phenylacetic acids has been developed in the presence of copper(ii) acetate. This tandem transformation involving carbon-carbon bond cleavage provides a complementary tool with particular application in the synthesis of secondary benzamides.
- Deng, Leiling,Huang, Bin,Liu, Yunyun
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supporting information
p. 1552 - 1556
(2018/03/08)
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- Ce(III)-catalyzed highly efficient synthesis of pyridyl benzamides from aminopyridines and nitroolefins without external oxidants
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An efficient synthesis of a variety of pyridyl benzamides from 2-aminopyridines and nitroolefins is described. This rare-earth-metal-catalyzed reaction provides the corresponding products with broad substrate scope in moderate to excellent yields, in the absence of additives and external oxidants. Water is used as the source of the carbonyl oxygen atom in pyridyl benzamides. Furthermore, 2-substituted oxazolo[4,5-b]pyridines are formed in good yields under the standard conditions when 2-aminopyridin-3-ols are used as the substrates.
- Chen, Zhengwang,Wen, Xiaowei,Qian, Yiping,Liang, Pei,Liu, Botao,Ye, Min
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supporting information
p. 1247 - 1251
(2018/03/06)
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- A Cross-Coupling Approach to Amide Bond Formation from Esters
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A palladium-catalyzed cross-coupling between aryl esters and anilines is reported, enabling access to diverse amides. The reaction takes place via activation of the C-O bond by oxidative addition with a Pd-NHC complex, which enables the use of relatively non-nucleophilic anilines that otherwise require stoichiometric activation with strong bases in order to react. High yields of aromatic, aliphatic, and heterocyclic products are obtained. A range of activated esters are evaluated in the presence and absence of catalyst, demonstrating that the catalytic methodology substantially increases the types of electrophiles that can be utilized for amide bond formation in the absence of harsh bases.
- Ben Halima, Taoufik,Vandavasi, Jaya Kishore,Shkoor, Mohanad,Newman, Stephen G.
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p. 2176 - 2180
(2017/08/09)
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- Transformation of aldehydes or alcohols to amides at room temperature under aqueous conditions
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A novel and efficient method for the synthesis of amide has been developed. The reactions proceeded smoothly under aqueous conditions at room temperature and generated the corresponding products in good to excellent yields. It is worth noting that alkyl amines which did not react in known approaches are well tolerated in our system.
- Dong, Dao-Qing,Hao, Shuang-Hong,Zhang, Hui,Wang, Zu-Li
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p. 1597 - 1599
(2017/07/17)
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- Microwave-assisted heteropolyanion-based ionic liquid promoted sustainable protocol to N-heteroaryl amides via N-directing dual catalyzed oxidative amidation of aldehydes
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A sustainable procedure for the synthesis of N-heteroaryl amides directly from oxidative amidation of aldehydes catalyzed by heteropolyanion-based ionic liquids under microwave-promoted conditions has been reported. The transformation has proven to tolerate a wide range of aldehydes and amino heterocycles with different functional groups. Moderate to excellent yields, solvent-free media, operational simplicity and reusability of catalysts are the main highlights. Furthermore, the proposed N-directing dual-catalysis mechanistic pathway was briefly investigated in this report.
- Fu, Renzhong,Yang, Yang,Jin, Weihua,Gu, Hui,Zeng, Xiaojun,Chai, Wen,Ma, Yunsheng,Wang, Quan,Yi, Jun,Yuan, Rongxin
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p. 107699 - 107707
(2016/11/29)
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- Metal-free oxidative amidation of aldehydes with aminopyridines employing aqueous hydrogen peroxide
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The first metal free report on the amidation of aldehydes with aminopyridines was accomplished using simple aqueous hydrogen peroxide (aq. H2O2) as the oxidant. No catalysts or additives were needed for this transformation and the reaction proceeded in water, an environmentally benign reaction medium. Green oxidant and reaction conditions, and the ability to construct diverse N-(pyridin-2-yl)benzamide by this elegant method render it a practical alternative for the synthesis of these amides.
- Sankari Devi,Alanthadka, Anitha,Tamilselvi,Nagarajan, Subbiah,Sridharan, Vellaisamy,Maheswari, C. Uma
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supporting information
p. 8228 - 8231
(2016/09/09)
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- Metal-free TBHP-mediated oxidative ring openings of 2-arylimidazopyridines via regioselective cleavage of C-C and C-N bonds
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A highly regioselective TBHP-mediated ring opening of imidazopyridines via cleavage of C-C and C-N bonds has been achieved for the first time to afford N-(pyridin-2-yl)benzamides. Preliminary mechanistic investigations revealed that the present metal-free
- Yan, Kelu,Yang, Daoshan,Wei, Wei,Li, Guoqing,Sun, Mingyang,Zhang, Qingyun,Tian, Laijin,Wang, Hua
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p. 100102 - 100105
(2015/12/05)
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- Copper-catalyzed highly efficient oxidative amidation of aldehydes with 2-aminopyridines in an aqueous micellar system
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An environmentally benign protocol for the synthesis of N-(pyridine-2-yl)amides from aldehydes and 2-aminopyridines has been developed under mild reaction conditions. This approach requires Cu(OTf)2 as a catalyst, and inexpensive molecular iodi
- Patel, Om P. S.,Anand, Devireddy,Maurya, Rahul K.,Yadav, Prem P.
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supporting information
p. 3728 - 3732
(2015/07/15)
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- Copper-catalysed amidation of 2-chloro-pyridines
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The simple and inexpensive N,N-dimethylcyclohexane-1,2-diamine/CuI catalytic system provides a versatile, easy and efficient access to an array of N-(2-pyridin-2-yl)-amides from 2-chloro-pyridine derivatives. The Royal Society of Chemistry 2013.
- Nicolas, Lionel,Angibaud, Patrick,Stansfield, Ian,Meerpoel, Lieven,Reymond, Sebastien,Cossy, Janine
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p. 18787 - 18790
(2013/10/22)
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- Copper-catalyzed dehydrogenative reaction: Synthesis of amide from aldehydes and aminopyridine
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We have developed a highly efficient method in the presence of copper catalyst to form amides from aminopyridines and aldehydes. This method is simple, environmental benign and has practical advantages in the amide synthesis.
- Yang, Sizhuo,Yan, Hao,Ren, Xiaoyu,Shi, Xiaokang,Li, Jian,Wang, Yuling,Huang, Guosheng
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supporting information
p. 6431 - 6435
(2013/07/26)
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- Complexes of silicon and phosphorus chlorides with nitrogen-containing bases as the condensing agents in the synthesis of amides
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High effectiveness of new condensing agents on the basis of complexes of silicon and phosphorus chlorides with nitrogen-containing bases in the synthesis of amides from carboxylic acids and amines and also in heterocyclization is shown. Factors affecting the readiness of formation of the amide bond and the yields of the final products are established.
- Besgubenko, L. V.,Pipko, S. E.,Sinitsa, A. D.
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p. 1382 - 1390,9
(2020/09/16)
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- N-phenacylpyridinium bromides as acid corrosion inhibitors
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The inhibiting effect of N-phenacylpyridinium bromides with the amide group in the pyridine ring on corrosion of carbon steel in 3 M sulfuric acid is studied. A relationship between the nature of substituents at the amide group and the corrosion-protectiv
- Yurchenko,Pogrebova,Pilipenko,Shubina
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p. 1117 - 1120
(2007/10/03)
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- Ru-catalyzed hydroamidation of alkenes and cooperative aminocarboxylation procedure with chelating formamide
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(Matrix presented) A strategy of chelation-assisted activation of formamide was employed to achieve hydroamidation of alkenes to generate one-carbon-elongated amides in moderate to good selectivity and yields. Also reported is the two-metal-catalyzed cooperative aminocarboxylation of aryl iodides, in which Ru is presumed to catalyze decarbonylation of formamide to release carbon monoxide and amine for the subsequent Pd-catalyzed aminocarboxylation routes, thus enabling the net transformation to be performed in the absence of external CO pressure.
- Ko, Sangwon,Han, Hoon,Chang, Sukbok
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p. 2687 - 2690
(2007/10/03)
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- Formation and Pyrolysis of 1-(2'-Pyridyl)-5-aryltetrazoles
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A number of 1-(2'-pyridyl)-5-aryltetrazoles (Va-k) have been obtained by the reaction of 2-aroylamidopyridines (III) with phosphorus pentachloride and azidolysis of the resulting imidoyl chlorides.The products obtained on pyrolysis of 1-(2'-pyridyl)-5-ary
- Rao, P. Jayaprasad,Reddy, K. Kondal
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p. 117 - 120
(2007/10/02)
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