- One-pot synthesis ofN-substituted benzannulated triazolesviastable arene diazonium salts
-
A mild and effective one-pot synthesis of 1,2,3-benzotriazin-4(3H)-ones and benzothiatriazine-1,1(2H)-dioxide analogues has been developed. The method involves the diazotisation and subsequent cyclisation of 2-aminobenzamides and 2-aminobenzenesulfonamidesviastable diazonium salts, prepared using a polymer-supported nitrite reagent andp-tosic acid. The transformation was compatible with a wide range of aryl functional groups and amide/sulfonamide-substituents and was used for the synthesis of pharmaceutically important targets. The synthetic utility of the one-pot diazotisaton-cyclisation process was further demonstrated with the preparation of an α-amino acid containing 1,2,3-benzotriazin-4(3H)-one.
- Faggyas, Réka J.,McGrory, Rochelle,Sutherland, Andrew
-
supporting information
p. 6127 - 6140
(2021/07/21)
-
- Method for reducing aromatic nitro into arylamine
-
The invention relates to a method for reducing aromatic nitro to arylamine. The method comprises the following steps: (1) taking an aromatic nitro compound as a raw material, water as a hydrogen source, a palladium compound, cheap and easy to obtain, as a catalyst and tetrahydroxydiboron as an additive to reduce nitro to obtain a product; (2) taking the aromatic nitro compound as the raw material, a copper salt, cheap and easy to obtain, as the catalyst, the tetrahydroxydiboron as the additive to reduce the nitro to obtain a product; and (3) taking the aromatic nitro compound as the raw material, water as the hydrogen source, and the tetrahydroxydiboron as the additive, without needing a metal catalyst, to reduce the nitro to obtain a product. A preparation method for the arylamine, which is provided by the invention, is mild in reaction condition, low in costs, environment-friendly, high in yield, and suitable for industrial production.
- -
-
Paragraph 0153-0156
(2020/07/15)
-
- Metal-free Reduction of Nitro Aromatics to Amines with B 2 (OH) 4 /H 2 O
-
A metal-free reduction of nitro aromatics mediated by diboronic acid with water as both the hydrogen donor and solvent under mild conditions has been developed. A series of aromatic amines were obtained with good functional group tolerance and in good yields.
- Chen, Danyi,Zhou, Yanmei,Zhou, Haifeng,Liu, Sensheng,Liu, Qixing,Zhang, Kaili,Uozumi, Yasuhiro
-
supporting information
p. 1765 - 1768
(2018/06/26)
-
- Water as a hydrogen source in palladium-catalyzed reduction and reductive amination of nitroarenes mediated by diboronic acid
-
An unprecedented palladium-catalyzed chemoselective reduction and reductive amination of nitroarenes with water as a hydrogen source mediated by diboronic acid have been discovered. A series of aryl amines containing various reducible functional groups were obtained in good to excellent yields.
- Zhou, Yanmei,Zhou, Haifeng,Liu, Sensheng,Pi, Danwei,Shen, Guanshuo
-
p. 3898 - 3904
(2017/06/13)
-
- Deep eutectic solvent mediated synthesis of quinazolinones and dihydroquinazolinones: Synthesis of natural products and drugs
-
A mild and greener protocol was developed to synthesize substituted quinazolinones and dihydroquinazolinones via deep eutectic solvent (DES) mediated cyclization with a series of aliphatic, aromatic, and heteroaromatic aldehydes in good to excellent yields. This greener strategy was further utilised to synthesize various quinazolinone natural products and drugs.
- Ghosh, Suman Kr,Nagarajan, Rajagopal
-
p. 27378 - 27387
(2016/04/04)
-
- Identification of potent orally active factor Xa inhibitors based on conjugation strategy and application of predictable fragment recommender system
-
Anticoagulant agents have emerged as a promising class of therapeutic drugs for the treatment and prevention of arterial and venous thrombosis. We investigated a series of novel orally active factor Xa inhibitors designed using our previously reported conjugation strategy to boost oral anticoagulant effect. Structural optimization of anthranilamide derivative 3 as a lead compound with installation of phenolic hydroxyl group and extensive exploration of the P1 binding element led to the identification of 5-chloro-N-(5-chloro-2-pyridyl)-3-hydroxy-2-{[4-(4-methyl-1,4-diazepan-1-yl)benzoyl]amino}benzamide (33, AS1468240) as a potent factor Xa inhibitor with significant oral anticoagulant activity. We also reported a newly developed Free-Wilson-like fragment recommender system based on the integration of R-group decomposition with collaborative filtering for the structural optimization process.
- Ishihara, Tsukasa,Koga, Yuji,Iwatsuki, Yoshiyuki,Hirayama, Fukushi
-
p. 277 - 289
(2015/02/05)
-
- Copper-catalyzed radical methylation/C-H amination/oxidation cascade for the synthesis of quinazolinones
-
A copper-catalyzed radical methylation/sp3 C-H amination/oxidation reaction for the facile synthesis of quinazolinone was developed. In this cascade reaction, dicumyl peroxide acts not only as a useful oxidant but also as an efficient methyl source. Notably, a methyl radical, generated from peroxide, was confirmed by electron paramagnetic resonance for the first time.
- Bao, Yajie,Yan, Yizhe,Xu, Kun,Su, Jihu,Zha, Zhenggen,Wang, Zhiyong
-
p. 4736 - 4742
(2015/05/13)
-
- Natural surfactant mediated phytosynthesis and solvatochromic fluorescence of 2-aminobenzamide derivatives
-
A green synthesis and intriguing solvatochromic behaviour of 2-aminobenzamide derivatives in varying solvents has been investigated. The biomaterial in the form of an aqueous extract of mesocarp of the fruit of the Balanites roxburghii plant as a natural surfactant reaction medium has been employed for phytosynthesis with quantitative yield at 60 °C. The reaction proceeds effortlessly in a short reaction time with easy product formation. The fluorescence property of some synthesized compounds was studied, along with the interesting solvatochromic behaviour of 2-amino-N-benzylbenzamide.
- More, Pallavi,Patil, Amol,Salunkhe, Rajashri
-
p. 63039 - 63047
(2015/02/19)
-
- Efficient syntheses of 2,3-disubstituted natural quinazolinones via iridium catalysis
-
Natural products sclerotigenin, pegamine, deoxyvasicinone, mackinazolinone, and rutaecarpine were synthesized. Core quinazolinone structures were constructed via Ir catalysis. The Royal Society of Chemistry 2012.
- Fang, Jie,Zhou, Jianguang
-
supporting information; experimental part
p. 2389 - 2391
(2012/04/11)
-
- Synthesis, antimicrobial evaluation, ot-QSAR and mt-QSAR studies of 2-amino benzoic acid derivatives
-
A series of 2-amino benzoic acid derivatives (1-28) were synthesized and evaluated for their in vitro antimicrobial activity against the panel of Gram positive, Gram negative bacterial and fungal strains. The results of antimicrobial studies indicated that, in general, the synthesized compounds were found to be bacteriostatic and fungistatic in action. QSAR studies performed by the development of one target and multi target models indicated that multi-target model was effective in describing the antimicrobial activity as well demonstrated the effect of structural parameters viz. LUMO, 3χv and W on antimicrobial activity of 2-amino benzoic acid derivatives. Springer Science+Business Media, LLC 2010.
- Mahiwal, Kuldeep,Kumar, Pradeep,Narasimhan, Balasubramanian
-
experimental part
p. 293 - 307
(2012/09/07)
-
- Cyclooxygenase-1-selective inhibitors are attractive candidates for analgesics that do not cause gastric damage. Design and in vitro/in vivo evaluation of a benzamide-type cyclooxygenase-1 selective inhibitor
-
Although cyclooxygenase-1 (COX-1) inhibition is thought to be a major mechanism of gastric damage by nonsteroidal anti-inflammatory drugs (NSAIDs), some COX-1-selective inhibitors exhibit strong analgesic effects without causing gastric damage. However, it is not clear whether their analgesic effects are attributable to COX-1-inhibitory activity or other bioactivities. Here, we report that N-(5-amino-2-pyridinyl)-4-(trifluoromethyl)benzamide (18f, TFAP), which has a structure clearly different from those of currently available COX-1-selective inhibitors, is a potent COX-1-selective inhibitor (COX-1 IC 50 = 0.80 ± 0.05 μM, COX-2 IC50 = 210 ± 10 μM). This compound causes little gastric damage in rats even at an oral dose of 300 mg/kg, though it has an analgesic effect at as low a dose as 10 mg/kg. Our results show that COX-1-selective inhibitors can be analgesic agents without causing gastric damage.
- Kakuta, Hiroki,Zheng, Xiaoxia,Oda, Hiroyuki,Harada, Shun,Sugimoto, Yukio,Sasaki, Kenji,Tai, Akihiro
-
p. 2400 - 2411
(2008/12/22)
-
- An efficient synthesis of 2,3-diaryl (3H)-quinazolin-4-ones via imidoyl chlorides
-
A practical and efficient three step synthetic route to 2,3-diaryl (3H)-quinazolin-4-ones has been developed. The key step involves microwave-assisted condensation of an imidoyl chloride with an aryl amine. This methodology affords the products cleanly and in high yields.
- Kalusa, Andrew,Chessum, Nicola,Jones, Keith
-
scheme or table
p. 5840 - 5842
(2009/04/05)
-
- Compounds for modulating TRPV3 function
-
The present application relates to compounds and methods for treating pain and other conditions related to TRPV3.
- -
-
Page/Page column 53
(2010/11/28)
-
- 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)
-
- Synthesis and in vitro study of platelet antiaggregant activity of 1,2,3,4-tetrahydroquinazoline derivatives
-
Some original 3-substituted 1,2,3,4-tetrahydroquinazolines were synthesized. Their antiplatelet activity was evaluated in vitro with respect to aggregation induced by the main inducers (ADP, collagen, arachidonic acid), platelet serotonin release reaction and thromboxane A2 synthesis. All these molecules possess an inhibiting power which, compared to that of aspirin in the same conditions, is the same or greater when aggregation is induced by ADP.
- Gravier,Dupin,Casadebaig,Hou,Boisseau,Bernard
-
p. 531 - 535
(2007/10/02)
-