- A facile synthesis of (Z)-1, 6-disubstituted-7H-benzo[b][1,5]diazonin-7-one derivatives via arylation-allylation-RCM pathway of anthranilamide and isatoic anhydride
-
A facile and efficient method has been developed for the synthesis of (Z)-6-allyl-1-phenyl-1,2,5,6-tetrahydro-7H-benzo[b][1,5]diazonin-7-one and (Z)-1,6-diphenyl-1,2,5,6-tetrahydro-7H-benzo[b][1,5]diazonin-7-one from anthranilamide via N-arylation/N-allylation and from isatoic anhydride via ring opening/N-arylation/N-allylation followed by ring closing metathesis using Grubbs-II catalyst as a key step. Grubbs-II catalyst was found to be superior over Grubbs-I catalyst in terms of reaction time and yield of the product, and the routes developed were suitable to synthesize benzo fused nine membered nitrogen heterocycles. The requirement of diallylated substrates with protected amine and amide nitrogen is suitable for RCM has been established for the synthesis of diazoninone derivatives.
- Novanna, Motakatla,Kannadasan, Sathananthan,Shanmugam, Ponnusamy
-
-
Read Online
- Amidation of polyaromatic carboxylic acids in aqueous medium
-
The amidation of polyaromatic carboxylic acids, such as 4- biphenylcarboxylic acid, 4-biphenylacetic acid, 4-carboxy-4'-hydroxybiphenyl, and N-phenylanthranilic acid, was satisfactorily carried out to give the corresponding amides using a wild-type bacter
- Maruyama, Reiji,Ono, Shin,Inoue, Masami
-
-
Read Online
- Unravelling the photophysics of triphenylamine and diphenylamine dyes: A comprehensive investigation with: Ortho -, meta - And para -amido substituted derivatives
-
The triphenylamine (TPA) and diphenylamine (DPA) derivatives constitute an important class of dyes that are suitable for many fluorescence-based applications. This study provides a thorough understanding about the photophysics of ortho-, meta- and para-am
- Mandare, Narendra,Shanmugam, Ponnusamy,Sundararajan, Mahesh,Dutta Choudhury, Sharmistha
-
-
Read Online
- Effects of amino acids on the amidation of polyaromatic carboxylic acids by Bacillus cereus.
-
The soil bacterium Bacillus cereus Tim-r01 efficiently transformed polyaromatic carboxylic acids (PACA) such as 4-biphenylcarboxylic acid (4-BPCA), 4-biphenylacetic acid, and 4-phenoxybenzoic acid into their corresponding amides. The amidation activity was expressed at 37 degrees C (pH 7-8) in the presence of grown cells in nutrients under an aerobic atmosphere. Other strains of B. cereus, IFO 3001 and IAM 1229, also gave the amide from 4-BPCA. In phosphate-buffered saline (PBS), the addition of normal amino acids was essential, while sulfur-containing amino acids such as methionine and cysteine drastically inhibited the amidation. Tracer experiments using N-15-isoleucine and N-15-alanine showed that the nitrogen atom of the amide came from an amino group of amino acids but not from ammonia or alkylamines.
- Maruyama,Kawata,Ono,Nishizawa,Ito,Inoue
-
-
Read Online
- Synthesis, biological screening, and molecular docking of quinazolinone and quinazolinethione as phosphodiesterase 7 inhibitors
-
N-Substituted isatoic anhydrides were used as starting materials for the synthesis of compounds 5–16 through alkali hydrolysis, Schiff base reactions, and oxidation. Compounds 18–23 were obtained by thionation of their oxo isosteres using Lawesson's reage
- Elfeky, Sherin M.,Sobahi, Tariq R.,Gineinah, Magdy M.,Ahmed, Nesreen S.
-
-
- An Efficient Ni/Pd Catalyzed Chemoselective Synthesis of 1,3,2-Benzodiazaborininones from Boronic Acids and Anthranilamides
-
An efficient Ni/Pd catalyzed chemoselective synthesis of 1,3,2-benzodiazaborininones from boronic acids and anthranilamide has been developed. This protocol allows for the rapid and straightforward access to a wide range of 1,3,2-benzodiazaborininones at roomtemperature with excellent functional group tolerance. (Figure presented.).
- Wang, Hao-Jie,Zhang, Mo,Li, Wen-Jing,Ni, Yu,Lin, Jin,Zhang, Zhan-Hui
-
p. 5018 - 5024
(2019/11/03)
-
- Synthesis of blue-red emissive amido-substituted di(het)aryl and tri(het)aryl amine derivatives via chemoselective N-mono and N,N-diarylation of (het) aryl amino amides using benzyne/arynes
-
Herein, via chemoselective N-mono and N,N-diarylation of an aryl/hetaryl amino amide reaction using benzyne or arynes, an amide-substituted triaryl amine derivative and diaryl amine derivatives were afforded. The scope and limitation of the present study have been studied. The products thus obtained were synthetically transformed to highly functionalized biphenyl bridged heterocycles via Suzuki coupling and condensation with 4,4′-biphenyl dialdehyde. Evaluation of the photophysical properties has revealed that the triaryl amine derivatives are blue emissive with high quantum yields, whereas the heterocyclic triaryl amine derivatives are blue-red emissive. The benzofuran-derived compound 4i was found to be blue emissive with high quantum yield, whereas the pyridine-derived compound 5j was found to be red emissive with low quantum yield.
- Meerakrishna, Ramakrishnan Suseela,Shanmugam, Ponnusamy
-
p. 2550 - 2558
(2019/02/14)
-
- Selective C-N coupling reaction of diaryliodonium salts and dinucleophiles
-
N-Aryl-α-amino amides including their chiral isomers have demonstrated important applications as pharmaceutical drugs; however, to date, a one-step synthetic route for them still remains to be developed. Herein, an efficient ligand-free copper-catalyzed selective C-N coupling reaction of diaryliodonium salts and dinucleophiles under mild conditions was realized. Diaryliodonium salts prefer to react with dinucleophiles at the site of stronger alkalic amino groups. Thus, a general aliphatic amino-selective N-arylation of α-amino amides was disclosed. Additionally, copper-catalyzed N-arylation of diaryliodonium salts afforded the same products as obtained via palladium-catalyzed reactions of aryl halides.
- Ma, Chang,Wu, Xufeng,Zeng, Qingle,Zhou, Lihong,Huang, Yi
-
supporting information
p. 2873 - 2877
(2017/04/14)
-
- Chemoselective: N -arylation of aminobenzamides via copper catalysed Chan-Evans-Lam reactions
-
Chemoselective N-arylation of unprotected aminobenzamides was achieved via Cu-catalysed Chan-Evans-Lam cross-coupling with aryl boronic acids for the first time. Simple copper catalysts enable the selective arylation of amino groups in ortho/meta/para-aminobenzamides under open-flask conditions. The reactions were scalable and compatible with a wide range of functional groups.
- Liu, Shuai,Zu, Weisai,Zhang, Jinli,Xu, Liang
-
supporting information
p. 9288 - 9292
(2017/11/23)
-
- Preparation method for arylamine benzamides compounds and N-aryl-arylamine benzamides compounds
-
The invention provides a preparation method for arylamine benzamides compounds and N-aryl-arylamine benzamides compounds and belongs to the technical field of refining. According to the method provided by the invention, carbon nitrogen coupling reaction is performed by using arylboronic acid (or borate) as an aryl reagent under a copper-catalyzed condition, the reaction is performed at 10-35 DEG C and the selective arylation of aminophenamide is realized. Compared with the present Buchwald-Hartwig carbon nitrogen coupling reaction under palladium-catalyzed condition, the carbon nitrogen coupling reaction has the advantages that the catalyst is low in cost and low in toxicity, the raw materials are simple, easily acquired, stable and low-toxicity, the reaction temperature is greatly reduced, inert gas atmosphere protection is not required, the stirring reaction can be directly performed in an opening reaction flask under a room temperature condition, the condition is mild and the operation is easy, aniline locally has high-selective arylation reaction, the reaction yield is high, the product is easily purified and the atom economy is high.
- -
-
Paragraph 0027; 0028; 0029; 0030; 0031
(2018/01/03)
-
- Naryl-substituted anthranilamides with intramolecular hydrogen bonds
-
Hydrogen bonding interaction as one type of non-covalent force has proven itself to be highly efficient for constructing structurally unique artificial secondary structures. Here, the structure of Naryl-substituted anthranilamide in solution is demonstrated by various NMR technique, the intramolecular hydrogen bonds between amide attached to arylamine of the same ring is proposed, which is supported by its crystal structure in the solid phase. The substituent on the nitrogen atom of arylamine plays an important role in forming the presence of intramolecular hydrogen bonds. The chemical shift of the Naryl-H downfield changes obviously, due to the formation of intramolecular hydrogen bonds and the deshielding effect of oxygen, and the neighboring C-H is activated and shows downfield protonic signal too. The presence of intramolecular hydrogen bonds probably provides the explanation for the transformation from Naryl-substituted anthranilamide to imine, which could be converted into 2-aryl quinazolinone finally.
- Wang, Li-Xia,Hu, Ben-Quan,Xiang, Jun-Feng,Cui, Jie,Hao, Xiang,Liang, Tong-Ling,Tang, Ya-Lin
-
supporting information
p. 8588 - 8591
(2014/12/11)
-
- NEW DS DNA BINDING FLUORESCENT DYES
-
The present invention is directed to a fluorescent dye comprising a benzothiazolium moiety and a pyrimidinium moiety connected by a mono-methine bridge, characterized in that (i) the 2-position of the pyrimidine carries a substituent which starts with a C
- -
-
Page/Page column 17; Sheet 1
(2008/12/05)
-
- Ligands for metals and improved metal-catalyzed processes based thereon
-
One aspect of the present invention relates to ligands for transition metals. A second aspect of the present invention relates to the use of catalysts comprising these ligands in transition metal-catalyzed carbon-heteroatom and carbon-carbon bond-forming reactions. The subject methods provide improvements in many features of the transition metal-catalyzed reactions, including the range of suitable substrates, reaction conditions, and efficiency.
- -
-
-
- Expanding Pd-catalyzed C-N bond-forming processes: The first amidation of aryl sulfonates, aqueous amination, and complementarity with Cu-catalyzed reactions
-
The first general method for the Pd-catalyzed amination of aryl tosylates and benzenesulfonates was developed utilizing ligand 1, which belongs to a new generation of biaryl monophosphine ligands. In addition, the new catalyst system for the first time enables amidation of aryl arenesulfonates and aqueous amination protocols that do not necessitate the use of cosolvents. The substrate scope has been significantly expanded to include aryl halides containing primary amides and free carboxylic acid groups. In the case of multifunctional substrates, the Pd-catalyzed amination can provide selectivity that is complementary to the Cu-catalyzed C-N bond-forming processes. Copyright
- Huang, Xiaohua,Anderson, Kevin W.,Zim, Danilo,Jiang, Lei,Klapars, Artis,Buchwald, Stephen L.
-
p. 6653 - 6655
(2007/10/03)
-
- 1-phenyl-4(1H)-quinazolinones and 2,3-dihydro-1-phenyl-4(1H)-quinazolinones as potential cholecystokinin receptor ligands
-
A series of new 1-phenyl-4(1H)-quinazolinones and 2,3-dihydro-1-phenyl-4(1H)-quinazolinones were synthesized and tested as cholecystokinin receptor ligands. All the compounds showed moderate affinity and 1-phenyl-4(1H)-quinazolinones resulted more effecti
- Pentassuglia, Giorgio,Bertani, Barbara,Donati, Daniele,Ursini, Antonella
-
p. 1163 - 1170
(2007/10/03)
-
