- Tert-Butyl Nitrite Mediated Synthesis of Fluorinated O-Alkyloxime Ether Derivatives
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A tert-butyl nitrite (TBN)-mediated synthesis of fluorinated O-alkyloxime ether derivatives with bromodifluoroalkyl reagents as the fluorine sources has been developed. A variety of halodifluorinated compounds were found compatible, delivering the desired
- Ma, Xingxing,Song, Qiuling
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- Manganese Catalyzed Direct Amidation of Esters with Amines
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The transition metal catalyzed amide bond forming reaction of esters with amines has been developed as an advanced approach for overcoming the shortcomings of traditional methods. The broad scope of substrates in transition metal catalyzed amidations remains a challenge. Here, a manganese(I)-catalyzed method for the direct synthesis of amides from a various number of esters and amines is reported with unprecedented substrate scope using a low catalyst loading. A wide range of aromatic, aliphatic, and heterocyclic esters, even in fatty acid esters, reacted with a diverse range of primary aryl amines, primary alkyl amines, and secondary alkyl amines to form amides. It is noteworthy that this approach provides the first example of the transition metal catalyzed amide bond forming reaction from fatty acid esters and amines. The acid-base mechanism for the manganese(I)-catalyzed direct amidation of esters with amines was elucidated by DFT calculations.
- Fu, Zhengqiang,Wang, Xinghua,Tao, Sheng,Bu, Qingqing,Wei, Donghui,Liu, Ning
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p. 2339 - 2358
(2021/02/03)
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- Acyl Cyanides as Bifunctional Reagent: Application in Copper-Catalyzed Cyanoamidation and Cyanoesterification Reaction
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Cu-catalyzed domino decyanation and cyanation reaction of acyl cyanides with amines or alcohols have been developed. The cyano sources were generated in situ via C-CN cleavage yielding the corresponding cyano substituted amides or esters in moderate to excellent yields. This approach features a cheap copper catalyst, domino decyanation and cyanation reaction, readily available starting materials, broad substrate scope, operational simplicity, and the potential for further transformation of the cyano group.
- Chen, Zhengwang,Wen, Xiaowei,Zheng, Weiping,He, Ruolan,Chen, Dou,Cao, Dingsheng,Long, Lipeng,Ye, Min
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p. 5691 - 5701
(2020/04/10)
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- Synthesis of 2-Amino-1,3-dienes from Propargyl Carbonates via Palladium-Catalyzed Carbon-Nitrogen Bond Formation
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A catalytic method to synthesize 1,3,-dienes from propargylic precursors is reported. This palladium-catalyzed carbon-nitrogen bond-forming reaction furnishes 2-amino-1,3-dienes in excellent yields (up to 98%) and shows a broad tolerance to functional group diversity. The reaction has been demonstrated for over 30 amine substrates, including anilines and indoles, and proceeds under mild neutral conditions. The resulting 1,3-dienes are of great synthetic interest because of their further reaction potential.
- O'Broin, Calvin Q.,Guiry, Patrick J.
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supporting information
p. 879 - 883
(2020/02/04)
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- Combined Cyanoborylation, C-H Activation Strategy for Styrene Functionalization
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A one-pot multicomponent copper-catalyzed protocol for borylation/ortho-cyanation of styrene derivatives followed by a Suzuki-Miyaura coupling provides a platform to explore the factors that control the selectivity between distal or proximal functionalization of arenes. The development of divergent nitrile-directed C-H functionalization (acetoxylation, pivalation, and methoxylation) offers an effective approach to rapidly increase synthetic complexity. Finally, the development of a mild reductive decyanation allows a traceless method to access functionalized biaryl motifs.
- Ansel, Annabel Q.,Montgomery, John
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supporting information
p. 8538 - 8543
(2020/11/12)
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- Method for preparing derivatives of benzamide under microwave condition in aqueous phase
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The invention discloses a method for preparing derivatives of benzamide under a microwave condition in an aqueous phase. A coupling reaction is carried out between substituted benzoic acid and amine under the microwave condition in the aqueous phase. The method for preparing the derivatives of benzamide is environmentally friendly, easy and convenient to operate, safe, low in cost and efficient. Compared with the prior art, the method can be applicable to a large number of functional groups, is high in yield, produces fewer by-products, and further is easy to operate, safe, low in cost and environmentally friendly. A formula is shown in the description.
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Paragraph 0019; 0050
(2019/03/28)
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- Method for synthesizing amide compound through photocatalysis in water phase
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The invention discloses a method for synthesizing an amide compound through photocatalysis in a water phase. The method comprises the following steps: putting catalysis amounts of a free radical initiator, an amine derivative, a carboxylic acid derivative, a phase transfer catalyst, an inorganic base and water into a reaction container, carrying out a reaction in a photocatalysis reaction instrument at certain power under a room temperature condition, after a certain time, carrying out extraction by using a small amount of ethyl acetate, and carrying out recrystallization, so as to obtain theamide compound, wherein the free radical initiator is eosin, methyl orange, sodium persulfate, ammonium persulfate or potassium peroxodisulfate, the phase transfer catalyst is tetrabutylammonium bromide, and the power of the photocatalytic reaction instrument is 5W. By adopting the method disclosed by the invention, toxic thionyl chloride or phosphorus oxychloride is not needed for a chlorinationreaction, water is adopted as a solvent, a novel photocatalysis method is used, and the amide compound with a high yield can be prepared through a room-temperature reaction for 2-5 hours with an incandescent light bulb of 5W, and in addition, the method is simple in aftertreatment, and low in cost and is an ideal green synthesis method of amide compounds.
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Paragraph 0061-0070
(2019/10/01)
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- Pd-Catalyzed tandem reaction of N-(2-cyanoaryl)benzamides with arylboronic acids: synthesis of quinazolines
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The synthesis of 2,4-disubstituted quinazolines by a palladium-catalyzed reaction of arylboronic acids with N-(2-cyanoaryl)benzamides has been developed with moderate to excellent yields. The method shows good functional group tolerance. In particular, ha
- Zhu, Jianghe,Shao, Yinlin,Hu, Kun,Qi, Linjun,Cheng, Tianxing,Chen, Jiuxi
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supporting information
p. 8596 - 8603
(2018/11/27)
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- Synthesis of 2-Aminobenzonitriles through Nitrosation Reaction and Sequential Iron(III)-Catalyzed C-C Bond Cleavage of 2-Arylindoles
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A variety of 2-aminobenzonitriles were prepared from 2-arylindoles in good to excellent yields through tert-butylnitrite (TBN)-mediated nitrosation and sequential iron(III)-catalyzed C-C Bond cleavage in a one-pot fashion. The 2-aminobenzonitriles can be used to rapidly synthesize benzoxazinones by intramolecular condensation. The present method features an inexpensive iron(III) catalyst, gram scalable preparations, and novel C-C bond cleavage of indoles.
- Chen, Wei-Li,Wu, Si-Yi,Mo, Xue-Ling,Wei, Liu-Xu,Liang, Cui,Mo, Dong-Liang
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p. 3527 - 3530
(2018/06/26)
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- Synthesizing method of drug intermediate quinazoline compound
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The invention relates to a quinazoline compound as shown in formula (5) and capable of being used as a drug intermediate and a synthesizing method of the quinazoline compound. The synthesizing methodhas the advantages that the method is completed through
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Paragraph 0063; 0065-0068; 0074; 0076-0079; 0084; 0086-0089
(2018/09/11)
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- Synthesis method of nitrogen-containing heterocyclic drug intermediates
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The invention relates to nitrogen-containing heterocyclic compounds which can be used as drug intermediates and are shown in the following formula (5) in the description and further provides a synthesis method of the nitrogen-containing heterocyclic compo
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Paragraph 0060; 0061; 0064; 0065; 0082-0086
(2018/09/11)
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- Fused heterocyclic pharmaceutical intermediate synthesis method
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The present invention relates to a fused heterocyclic compound capable of being used as a pharmaceutical intermediate and represented by the following formula (5) defined in the specification, and provides a synthesis method of the fused heterocyclic comp
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Paragraph 0058-0063; 0069; 0072; 0073; 0078-0082; 0086-0091
(2018/11/22)
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- Structure activity relationships, multidrug resistance reversal and selectivity of heteroarylphenyl ABCG2 inhibitors
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An overexpression of the transmembrane ATP-binding cassette transporter G2 (ABCG2, BCRP) in cancer tissues is supposed to play a role in the multidrug resistance (MDR) of tumors resulting in an inefficient chemotherapy. Therefore, co-administration of sel
- K?hler, Sebastian C.,Vahdati, Sahel,Scholz, Matthias S.,Wiese, Michael
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p. 483 - 500
(2018/02/14)
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- Efficient and Mild Ullmann-Type N-Arylation of Amides, Carbamates, and Azoles in Water
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A simple, sustainable, efficient, mild, and low-cost protocol was developed for d-glucose-assisted Cu-catalyzed Ullmann reactions in water for amides, carbamates, and nitrogen-containing heterocycles. The reaction was compatible with diverse aryl/heteroaryl iodides, giving highly substituted pyridine, indole, or indazole rings. This method offers an attractive alternative to existing protocols, because the reaction proceeds in aqueous media, occurs at or near ambient temperature, and provides the N-arylated products in good to high yields.
- Bollenbach, Maud,Aquino, Pedro G. V.,de Araújo-Júnior, Jo?o Xavier,Bourguignon, Jean-Jacques,Bihel, Frédéric,Salomé, Christophe,Wagner, Patrick,Schmitt, Martine
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supporting information
p. 13676 - 13683
(2017/10/10)
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- Detection of weak hydrogen bonding to fluoro and nitro groups in solution using H/D exchange
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Hydrogen/deuterium (H/D) exchange can be a sensitive technique for measuring the strength of hydrogen bonding to neutral organic nitro and fluoro groups. The slower rates of reaction in comparison to suitable controls suggest that hydrogen bonding is present, albeit rather weak.
- Shugrue,Defrancisco,Metrano,Brink,Nomoto,Linton
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supporting information
p. 2223 - 2227
(2016/03/01)
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- 2-Amino[1,2,4]triazolo[1,5-c]quinazolines and Derived Novel Heterocycles: Syntheses and Structure–Activity Relationships of Potent Adenosine Receptor Antagonists
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2-Amino[1,2,4]triazolo[1,5-c]quinazolines were identified as potent adenosine receptor (AR) antagonists. Synthetic strategies were devised to gain access to a broad range of derivatives including novel polyheterocyclic compounds. Potent and selective A3AR antagonists were discovered, including 3,5-diphenyl[1,2,4]triazolo[4,3-c]quinazoline (17, Kihuman A3AR 1.16 nm) and 5′-phenyl-1,2-dihydro-3′H-spiro[indole-3,2′-[1,2,4]triazolo[1,5-c]quinazolin]-2-one (20, Kihuman A3AR 6.94 nm). In addition, multitarget antagonists were obtained, such as the dual A1/A3antagonist 2,5-diphenyl[1,2,4]triazolo[1,5-c]quinazoline (13 b, Kihuman A1AR 51.6 nm, human A3AR 11.1 nm), and the balanced pan-AR antagonists 5-(2-thienyl)[1,2,4]triazolo[1,5-c]quinazolin-2-amine (11 c, Kihuman A1AR 131 nm, A2AAR 32.7 nm, A2BAR 150 nm, A3AR 47.5 nm) and 9-bromo-5-phenyl[1,2,4]triazolo[1,5-c]quinazolin-2-amine (11 q, Kihuman A1AR 67.7 nm, A2AAR 13.6 nm, A2BAR 75.0 nm, A3AR 703 nm). In many cases, significantly different affinities for human and rat receptors were observed, which emphasizes the need for caution in extrapolating conclusions between different species.
- Burbiel, Joachim C.,Ghattas, Wadih,Küppers, Petra,K?se, Meryem,Lacher, Svenja,Herzner, Anna-Maria,Kombu, Rajan Subramanian,Akkinepally, Raghuram Rao,Hockemeyer, J?rg,Müller, Christa E.
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p. 2272 - 2286
(2016/10/25)
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- The reaction of 2-(acylamino)benzonitriles with primary aromatic amines: A convenient synthesis of 2-substituted 4-(arylamino)quinazolines
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Abstract 2-Substituted 4-(arylamino)quinazolines were prepared from 2-(acylamino)benzonitriles and primary arylamines by refluxing in either ethanol using trifluoroacetic acid as a catalyst or acetic acid. The 2-aminobenzonitrile was acylated by reaction with anhydrides, isocyanates, or ethyl chloroformate at room temperature.
- Marinho, Elina,Proen?a, M. Fernanda
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supporting information
p. 1623 - 1632
(2015/03/30)
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- Copper-catalyzed oxidative ring closure of ortho-cyanoanilides with hypervalent iodonium salts: Arylation-ring closure approach to iminobenzoxazines
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A novel, highly modular synthetic methodology with high functional group tolerance was developed for the construction of iminobenzoxazine derivatives from ortho-cyanoanilides and diaryliodonium triflates via an oxidative arylation-cyclization path. The reaction is supposed to involve the formation of highly active aryl-copper(III) species. In this novel transformation, copper(II) triflate was used as catalyst in 1,2-dichloroethane or ethyl acetate and the reaction takes place at 75 °C in 2-16 h.
- Aradi, Klra,Novk, Zoltn
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supporting information
p. 371 - 376
(2015/03/05)
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- Palladium-catalyzed carbonylative synthesis of N-(2-cyanoaryl)benzamides and sequential synthesis of quinazolinones
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A convenient procedure for the synthesis of N-(2-cyanoaryl)benzamides has been developed. Using aryl bromides and 2-aminobenzonitriles as the substrates, Mo(CO)6 as the CO source, the desired amides were produced in good yields. Quinazolinones
- Wu, Xiao-Feng,Oschatz, Stefan,Sharif, Muhammad,Beller, Matthias,Langer, Peter
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supporting information
p. 23 - 29
(2014/01/06)
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- Substituted Nitrogen Heterocycles and Synthesis and Uses Thereof
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The invention relates to a nitrogen heterocycle compound of formula 1: Also disclosed are a method of synthesizing the compound and use of the compound for treating various diseases and conditions.
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Page/Page column 38
(2009/10/06)
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- Synthesis of quinazolinone analogues using sodium perborate as catalyst
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An environmentally benign approach for the synthesis of 2-aryl-3H-quinazolin-4-ones employing sodium perborate (SPB) as catalyst is described. SPB in water and acetone system is proved as selective catalyst of hydration for cyanides. The rate enhancement
- Kidwai, Mazaahir,Priya
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experimental part
p. 1876 - 1881
(2009/05/26)
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- Study of reaction between triphenylphosphine and activated acetylenic esters in the presence of benzanilide and some its derivatives
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Triphenylphosphine reacts with dialkyl acetylenedicarboxylates in the presence of NH-acids, such as benzanilide, 2-cyanobenzanilide, N-(2-acetylphenyl)benzamide, 3-nitrobenzanilide and methyl 2-benzamidobenzoate to generate stable phosphorus ylides. These stable ylides exist in solution as a mixture of two geometrical isomers as a result of restricted rotation around the carbon-carbon partial double bond resulting from conjugation of the ylide moiety with the adjacent carbonyl group.
- Hazeri, Nourollah,Maghsoodlou, Malek Taher,Khorassani, Sayyed Mostafa Habibi,Nassiri, Mahmoud,Afarini, Zahra
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experimental part
p. 97 - 100
(2009/07/18)
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- A combinatorial approach towards 2-acyl-3-amino-indole derivatives
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A widely applicable reaction sequence towards functionalised 2-acyl-3-amino-indole derivatives is presented. A set of 205 indole derivatives were prepared, in a solution phase combinatorial fashion, by coupling a reliable reaction protocol to a rapid puri
- Nettekoven
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p. 8251 - 8254
(2007/10/03)
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- v-Triazolines. XXXIX [1]. l,2,4-Triaryl-3-aminopyrroles. Unusual Reaction Products in the Pyrolysis of 5-Amino-v-triazolines and the Crystal Structure of 2-(3-Morpholin-4-yl-2,4-pyrrol-l-yl)benzonitrile
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Pyrolysis of 4-aryl-5-amino-v-triazolines affords, generally, amidines and/or benzanilides. Pyrolysis of 4-aryl-5-morpholino-v-triazolines 6, together with the expected amidines 7 and/or aryanilides 8, produced the morpholinopyrroles 9. The reaction mecha
- Pocar, Donato,Trimarco, Pasqualina,Bombieri, Gabriella
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p. 687 - 692
(2007/10/03)
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- Anchimeric Assistance in the Specific Acid-catalyzed Hydration of Benzonitriles
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2-(Acylamido)benzonitriles react to give exclusively the corresponding 2-(acylamido)benzamides under relatively mild aqueous acid conditions.The kinetics for hydration at 50 deg C in aqueous HCl with ionic strength kept at 1 mol dm-3 with KCl o
- Smyth, Richard M.,Williams, Andrew
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p. 2171 - 2174
(2007/10/02)
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