- KOtBu-Promoted Transition-Metal-Free Transamidation of Primary and Tertiary Amides with Amines
-
This work discloses transamidation of primary and tertiary amides with a range of aryl, heteroaryl, and aliphatic amines using potassium tert-butoxide. The reaction proceeds at room temperature under transition-metal-free conditions providing secondary amides in high yields. Moreover, reaction of cyclopropyl amine with tertiary amides proceeds with ring-opening to provide a rapid access to enamides.
- Ghosh, Tridev,Jana, Snehasish,Dash, Jyotirmayee
-
supporting information
p. 6690 - 6694
(2019/09/12)
-
- Nitrile Hydration Reaction Using Copper Iodide/Cesium Carbonate/DBU in Nitromethane-Water
-
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
-
supporting information
p. 2061 - 2065
(2018/09/14)
-
- Pd-Catalyzed tandem reaction of N-(2-cyanoaryl)benzamides with arylboronic acids: synthesis of quinazolines
-
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
-
supporting information
p. 8596 - 8603
(2018/11/27)
-
- 9-Deazapurines as Broad-Spectrum Inhibitors of the ABC Transport Proteins P-Glycoprotein, Multidrug Resistance-Associated Protein 1, and Breast Cancer Resistance Protein
-
P-Glycoprotein (P-gp, ABCB1), multidrug resistance-associated protein 1 (MRP1, ABCC1), and breast cancer resistance protein (BCRP, ABCG2) are the three major ABC transport proteins conferring resistance to many structurally diverse anticancer agents, lead
- Stefan, Katja,Schmitt, Sven Marcel,Wiese, Michael
-
p. 8758 - 8780
(2017/11/15)
-
- Synthesis of 2-methylbenzoxazoles directly from: N -phenylacetamides catalyzed by palladium acetate
-
A method to synthesize 2-methylbenzoxazoles directly from N-phenylacetamides catalyzed by Pd(OAc)2 in the presence of K2S2O8 and TfOH has been developed. The desired products were obtained in moderate to excellent yields. This approach provides a facile procedure to prepare benzoxazoles with available substrates. It is found that TfOH is the key factor for this cyclization reaction. A plausible mechanism of the reaction is proposed according to the control reactions and the literature.
- Wang, Biying,Jiang, Chengfei,Qian, Jiasheng,Zhang, Shuwei,Jia, Xiaodong,Yuan, Yu
-
p. 101 - 107
(2017/12/27)
-
- Palladium-Catalyzed Regioselective Direct Cyanation of Acetanilide Derivatives with K4[Fe(CN)6] by C–H Bond Activation
-
A practical, versatile, and efficient method for the palladium-catalyzed direct cyanation of readily available acetanilides with K4[Fe(CN)6] as a safe cyanating agent through C–H bond activation with excellent C2 regioselectivity was developed. This finding represents a new strategy for the synthesis of N-(2-cyanoaryl)acetamides, which are important structural motifs in natural products and pharmaceuticals.
- Kianmehr, Ebrahim,Faghih, Nasser,Tanbakouchian, Arezoo,Mahdavi, Mohammad
-
p. 4269 - 4274
(2016/09/14)
-
- Copper-catalyzed oxidative ring closure of ortho-cyanoanilides with hypervalent iodonium salts: Arylation-ring closure approach to iminobenzoxazines
-
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
-
supporting information
p. 371 - 376
(2015/03/05)
-
- The reaction of 2-(acylamino)benzonitriles with primary aromatic amines: A convenient synthesis of 2-substituted 4-(arylamino)quinazolines
-
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
-
supporting information
p. 1623 - 1632
(2015/03/30)
-
- Convenient N-acetylation of amines in N,N-dimethylacetamide with N,N-carbonyldiimidazole
-
Dimethylacetamide (DMAc) acts as an efficient source of acetyl and dimethylamine gas in the presence of N,N-carbonyldiimidazole (CDI). Addition of amines to the reaction mixture delivers the corresponding amides in good to excellent yields. The acetylation of amines reported herein, which relies on the in situ generation of N-acetylimidazole on warming of DMAc with CDI at 120-125 °C, serves as a convenient alternative to other acetylation methods.
- Chikkulapalli, Anil,Aavula, Sanjeev Kumar,Mona Np, Rifahath,Karthikeyan, Karthikeyan,Kumar C.H., Vinodh,Sulur G., Manjunatha,Sumathi, Shanmugam
-
supporting information
p. 3799 - 3803
(2015/06/08)
-
- Preparation and characterization of multi-walled carbon nanotubes (MWCNTs), functionalized with phosphonic acid (MWCNTs-C-PO3H2) and its application as a novel, efficient, heterogeneous, highly selective and reusable catalyst for acetylation of alcohols, phenols, aromatic amines, and thiols
-
A novel, efficient, heterogeneous, and reusable multi-walled carbon nanotubes (MWCNTs), functionalized with phosphonic acid (MWCNTs-C-PO 3H2) has been synthesized. The synthesized CNTs were characterized using some electron microscopic techniques such as scanning electron microscopy (SEM), atomic force microscopy (AFM), Energy dispersive X-ray spectroscopy (EDAX), and also some thermal and spectroscopic methods such as thermogravimetry (TG). The nitrogen adsorption behavior of the MWCNTs-C-PO3H2 catalyst was evaluated using the TG instrumentation system at 25°C. The catalyst was applied successfully for highly efficient and selective acetylation of alcohols, phenols, thiols and aromatic amines with acetic anhydride at room temperature under solvent-free conditions. The reusability of the catalyst was checked and the recovered catalyst was reused for five runs without significant loss in activity.
- Dehghani, Farzaneh,Sardarian, Ali Reza,Doroodmand, Mohammad Mehdi
-
p. 673 - 684
(2014/05/20)
-
- Copper-mediated cyanation of aryl halides by activation of benzyl cyanide as the cyanide source
-
Aryl nitriles were efficiently synthesized through copper-mediated cyanation of aryl halides using benzyl cyanide as the cyanide source. Aryl halides with various substituents on the aromatic ring afforded the corresponding aryl nitriles in 32-97 % yields (25 examples). This reaction could also be carried on a gram scale by using commercially available reagents. Additionally, a C-H bond oxidation and a C-CN cleavage are proposed to be involved in this cascade process. An efficient, copper-mediated cascade synthesis of aryl nitriles from aryl halides using benzyl cyanide as the cyanide source is described. Compared with traditional copper-mediated cyanation reactions, this approach effectively avoided the use of toxic MCN and low soluble reagents. Furthermore, C-H oxidation and C-CN cleavage are proposed to be involved in this cascade process. Copyright
- Wen, Qiaodong,Jin, Jisong,Mei, Yuncai,Lu, Ping,Wang, Yanguang
-
p. 4032 - 4036
(2013/07/11)
-
- PYRIDO [3',2' :4,5] THIENO [3, 2-D] PYRIMIDIN- 4 - YLAMINE DERIVATIVES AND THEIR THERAPEUTICAL USE
-
The present invention pertains generally to the field of therapeutic compounds, and more specifically to certain fused triaryl amine compounds of the following formula (for convenience, collectively referred to herein as "FTA compounds"), which, inter alia, inhibit LIM kinase (LIMK) activity. The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, to inhibit LIMK activity, and in the treatment of diseases and conditions that are mediated by LIMK, that are ameliorated by the inhibition of LIMK activity, etc., including proliferative conditions such as cancer (e.g., breast cancer, prostate cancer, melanoma, glioma, etc.), as well as vasodilation (including, e.g., hypertension, angina, cerebral vasospasm, and ischemia following subarachnoid hemorrhage), neurodegenerative disorders, atherosclerosis, fibrosis, and inflammatory diseases (including, e.g., Crohn's disease and chronic obstructive pulmonary disease (COPD)), and glaucoma (also known as ocular hypertension).
- -
-
Page/Page column 109-110
(2012/10/18)
-
- Iron-doped single-walled carbon nanotubes as new heterogeneous and highly efficient catalyst for acylation of alcohols, phenols, carboxylic acids and amines under solvent-free conditions
-
Iron-doped single-walled carbon nanotubes (Fe/SWCNTs) represent an efficient and new heterogeneous reusable catalyst for the acylation of a variety of alcohols, phenols, carboxylic acids and amines with acid chlorides or acid anhydrides under solvent-free conditions. The reactions of various primary, secondary, tertiary, and benzylic alcohols, diols, phenols, as well as aromatic and aliphatic amines give acylated adducts in good to excellent yields.
- Sharghi, Hashem,Jokar, Mahboubeh,Doroodmand, Mohammad Mahdi
-
experimental part
p. 426 - 442
(2011/04/15)
-
- Microwave-assisted synthesis of nano-sized cadmium oxide as a new and highly efficient catalyst for solvent free acylation of amines and alcohols
-
In present studies, a new and efficient method for synthesis of cadmium oxide nanoparticles by using microwave (MW) activation is reported. To ensure the specific efficiency of microwave irradiation versus conventional heating, the synthesis of Cd(OH)2 as precursor of CdO was carried out under similar temperature (80 °C), time and reaction conditions without microwave irradiation. The formation of CdO was characterized by XRD, TEM, FT-IR analysis. Catalytic activity of CdO nanopowder for acylation of alcohols, phenols and amines has been investigated. The results show that the reaction times and yields of desired products were improved by using CdO.
- Mazaheritehrani,Asghari,Orimi, R. Lotfi,Pahlavan
-
experimental part
p. 2554 - 2564
(2010/10/21)
-
- Palladium acetate catalyzed cyanation of aryl halides using Buchwald's 2-(di-t-butylphosphino)-1,1'-binaphthyl
-
An application of Buchwald's 2-(di-t-butylphosphino)-1,1'-binaphthyl 1 in palladium acetate catalyzed cyanation of aryl halides was developed. Using this ligand, aryl chlorides substituted with both electron donating or withdrawing groups afforded the desired cyano products in excellent yields. The corresponding aryl bromides gave higher yields within shorter time. Heteroaryl chlorides also reacted under the similar conditions to give the cyano products in excellent yields.
- Wang, Bei,Zhao, Rulin,Chen, Bang-Chi,Balasubramanian, Balu
-
experimental part
p. 47 - 52
(2010/09/09)
-
- Methods for treating or preventing erectile dysfunction or urinary incontinence
-
The present invention relates to methods for treating or preventing erectile dysfunction or urinary incontinence, comprising administering to a subject in need thereof an effective amount of a compound of the invention.
- -
-
Page/Page column 56
(2010/02/15)
-
- Zinc oxide (ZnO) as a new, highly efficient, and reusable catalyst for acylation of alcohols, phenols and amines under solvent free conditions
-
Zinc oxide (ZnO) is a highly efficient catalyst for the acylation of a variety of alcohols, phenols and amines with acid chlorides or acid anhydrides under solvent free conditions. Primary, secondary, tertiary, allylic and benzylic alcohols, diols and phenols with electron donating or withdrawing substituents can be easily acylated in good to excellent yield.
- Hosseini Sarvari, Mona,Sharghi, Hashem
-
p. 10903 - 10907
(2007/10/03)
-
- Isoquinoline derivatives and methods of use thereof
-
The invention provides novel classes of Isoquinoline Derivatives. Pharmaceutical compositions and methods of making and using the compounds, are also described.
- -
-
-
- Isoquinoline derivatives and methods of use thereof
-
The invention provides novel classes of Isoquinoline Derivatives. Pharmaceutical compositions and methods of making and using the compounds, are also described.
- -
-
-
- Indium-mediated one-pot reductive conversion of nitroarenes to N-arylacetamides
-
N-Arylacetamides were prepared in excellent yields from nitroarenes in the presence of acetic anhydride, acetic acid and indium by a one-pot procedure.
- Kim, Byeong Hyo,Han, Rongbi,Piao, Fengyu,Jun, Young Moo,Baik, Woonphil,Lee, Byung Min
-
-
- Synthesis and X-ray characterisation of a new polycondensed heterocycle obtained by a novel Mn(III)-mediated cascade reaction of 2-cyanophenyl isothiocyanate
-
2-Cyanophenyl isothiocyanate reacted with Mn(III) acetate in acetic acid or acetonitrile to give fair yields of a new polycondensed heterocycle arising from the joining together of two molecules of the starting isothiocyanate with loss of a CS moiety. The yields were close to 90% when the reaction was carried out in the presence of diethyl malonate. This compound was unambiguously identified by X-ray crystallography. Under the same conditions, 2-(methoxycarbonyl)phenyl isothiocyanate gave a quinazolinimine derivative instead which is likely to arise from cyclisation of an intermediate N,N′-diarylthiourea. The mechanism of formation of the former compound probably involves formation of a N,N′-bis(2-cyanophenyl)thiourea, followed by rearrangement and radical tandem ring closure of the corresponding cyclic imine derivative. This hypothesis is also supported by semiempirical calculations.
- Calestani, Gianluca,Capella, Laura,Leardini, Rino,Minozzi, Matteo,Nanni, Daniele,Papa, Romina,Zanardi, Giuseppe
-
p. 7221 - 7233
(2007/10/03)
-
- Nitrile Sulphides. Part 7. Synthesis of Benzopyranoisothiazoles and Isothiazoloquinolines
-
o-Hydroxybenzonitrile sulphide (1a), generated by thermal decarboxylation of the corresponding 1,3,4-oxathiazol-2-one, reacts with dimethyl acetylenedicarboxylate to afford methyl 4-oxo-4H-benzopyranoisothiazole-3-carboxylate (6a), from which the parent ring system (6c) can be prepared by hydrolysis and decarboxylation.The same products are formed from the acetoxy analogue (1b) via hydrolysis of isothiazole (5b). o-Acetamidobenzonitrile sulphide (1c) reacts similarly forming isothiazole (5c) and subsequently isothiazoloquinolin-4(5H)-one (7c) by hydrolysis, ring closure, and decarboxylation.Cycloadditions to ethyl cyanoformate, ethyl propiolate, and diethyl fumarate have also been examined.
- Brownsort, Peter A.,Paton, Michael
-
p. 2339 - 2344
(2007/10/02)
-
- SYNTHESIS OF 2,3,5,6-TETRAHYDRO-1H,4H,11cH-3a,6a,11b-TRIAZABENZANTHRACENE (5) AND X-RAY CRYSTAL STRUCTURE DETERMINATIONS OF (5), HEXAHYDRO-1H,4H,7H,9bH-3a,6a,9a-TRIAZAPHENALENE (1), BENZO-1,5,9-TRIAZADODECANE N,N',N''-TRITOSYLAMIDE, AND OF 1,5,9-TRIAZADODECANE N,N'N''-TRITOSYLAMID
-
The synthesis of 2,3,5,6-tetrahydro-1H,4H,11cH-3a,6a,11b-triazabenzanthracene (5) is described.X-ray crystal structure determinations on hexahydro-1H,4H,7H,9bH-3a,6a,9a-triazaphenalene (1) and its benzoanaloque (5) show them to adopt differing conformations; the reasons for this are discussed.
- Beddoes, Roy L.,Edwards, W. D.,Joule, J. A.,Mills, O. S.,Street, J. D.
-
p. 1903 - 1920
(2007/10/02)
-