7039-50-1Relevant academic research and scientific papers
Facile Access to Triazole-Fused 3,1-Benzoxazines Enabled by Metal-Free Base-Promoted Intramolecular C-O Coupling
Tatevosyan, Stepan S.,Kotovshchikov, Yury N.,Latyshev, Gennadij V.,Lukashev, Nikolay V.,Beletskaya, Irina P.
supporting information, p. 369 - 377 (2021/10/21)
A convenient approach to assemble 1,2,3-triazole-fused 4 H -3,1-benzoxazines has been developed. Diverse alcohol-tethered 5-iodotriazoles, readily accessible by a modified protocol of Cu-catalyzed (3+2)-cycloaddition, were utilized as precursors of the target fused heterocycles. The intramolecular C-O coupling proceeded efficiently under base-mediated transition-metal-free conditions, furnishing cyclization products in yields up to 96%. Suppression of the competing reductive cleavage of the C-I bond was achieved by the use of Na 2CO 3in acetonitrile at 100 °C. This practical and cost-effective procedure features a broad substrate scope and valuable functional group tolerance.
Ruthenium complexes of phosphine-amide based ligands as efficient catalysts for transfer hydrogenation reactions
Yadav, Samanta,Vijayan, Paranthaman,Yadav, Sunil,Gupta, Rajeev
, p. 3269 - 3279 (2021/03/16)
This work presents three mononuclear Ru(ii) complexes of tridentate phosphine-carboxamide based ligands providing a NNP coordination environment. The octahedral Ru(ii) ion shows additional coordination with co-ligands; CO, Cl and CH3OH. All three Ru(ii) complexes were thoroughly characterized including their crystal structures. These Ru(ii) complexes were utilized as catalysts for the transfer hydrogenation of assorted carbonyl compounds, including some challenging biologically relevant substrates, using isopropanol as the hydrogen source. The binding studies illustrated the coordination of the isopropoxide ion by replacing a Ru-ligated chloride ion followed by the generation of the Ru-H intermediate that was isolated and characterized and was found to be involved in the catalysis.
An efficient iron-promoted synthesis of 6H-indolo[2,3- b] quinolines and neocryptolepine derivatives
Yan, Zicong,Wan, Changfeng,Wan, Jianyong,Wang, Zhiyong
supporting information, p. 4405 - 4408 (2016/06/06)
A facile and practical method for the preparation of 6H-indolo[2,3-b]quinolines and neocryptolepines was developed under the promotion of the easily available ferric trichloride, affording the desired products with moderate to good yields.
A simple route to polysubstituted indoles exploiting azide induced furan ring opening
Abaev, Vladimir T.,Plieva, Anastasiya T.,Chalikidi, Petrakis N.,Uchuskin, Maxim G.,Trushkov, Igor V.,Butin, Alexander V.
supporting information, p. 4150 - 4153 (2014/09/30)
A straightforward, efficient indole synthesis based on thermolysis of 2-(2-azidobenzyl)furans with attack of the formed nitrene moiety onto the ipso position of furan ring has been developed. The cyclization is accompanied by furan ring opening and affords indoles with a 2-acylvinyl substituent suitable for further modifications.
Metal-free intramolecular oxidative decarboxylative amination of primary α-amino acids with product selectivity
Yan, Yizhe,Wang, Zhiyong
, p. 9513 - 9515 (2011/10/01)
A novel metal-free intramolecular oxidative decarboxylative coupling of primary α-amino acids with 2-aminobenzoketones under mild and neutral conditions was developed. Different quinazolines can be selectively obtained by various oxidants.
Discovery of a new 2-aminobenzhydrol template for highly potent squalene synthase inhibitors
Ichikawa, Masanori,Yokomizo, Aki,Itoh, Masao,Sugita, Kazuyuki,Usui, Hiroyuki,Shimizu, Hironari,Suzuki, Makoto,Terayama, Koji,Kanda, Akira
scheme or table, p. 1930 - 1949 (2011/05/03)
To obtain small and efficient squalene synthase inhibitors, a flexible 2-aminobenzhydrol open form structure was designed and showed potent inhibitory activity comparable to 4,1-benzoxazepin compounds. Further chemical modification led to the discovery of a novel template with a strong squalene synthase inhibitory activity, and its basic structure-activity relationship was revealed. The X-ray crystallographic data of compound 12 bound to the active site of squalene synthase provided an important insight into the binding mode of this alternative template that formed 11-membered ring conformations with an intramolecular hydrogen bond.
A simple and efficient approach to the synthesis of 2-phenylquinazolines via sp3 C-H functionalization
Zhang, Jintang,Zhu, Dapeng,Yu, Chenmin,Wan, Changfeng,Wang, Zhiyong
supporting information; experimental part, p. 2841 - 2843 (2010/09/04)
(Figure presented) A facile and novel approach to the synthesis of 2-phenylquinazolines was developed via a tandem reaction following sp 3 C-H functionalization. Twenty-five examples of 2-phenylquinazolines were obtained from easily available 2-aminobenzophenones and benzylic amines with good to excellent yields.
A novel and efficient methodology for the construction of quinazolines based on supported copper oxide nanoparticles
Zhang, Jintang,Yu, Chenmin,Wang, Sujing,Wan, Changfeng,Wang, Zhiyong
supporting information; experimental part, p. 5244 - 5246 (2010/09/05)
A series of quinazolines were synthesized from 2-aminobenzophenones and benzylic amines in good to excellent yields by employing a new heterogeneous catalyst based on the copper oxide nanoparticles supported on kaolin.
An enantiopure galactose oxidase model: synthesis of chiral amino alcohols through oxidative kinetic resolution catalyzed by a chiral copper complex
Mannam, Sreedevi,Sekar, Govindasamy
experimental part, p. 497 - 502 (2009/07/18)
An enantiopure galactose oxidase (GO) enzyme model has been synthesized from readily available (R)-BINAM and Cu(OTf)2, and the enantiopure GO model has been effectively used in situ as an efficient chiral catalyst for the synthesis of chiral amino alcohols through oxidative kinetic resolution (OKR), where molecular oxygen is used as the sole oxidant. Under the proposed catalytic conditions, both ortho- and para-substituted amino alcohols were resolved with good to excellent enantiomeric excesses through oxidative kinetic resolution.
A flexible synthesis of 2,3-disubstituted indoles from aminobenzyl phosphonium salts. A direct synthesis of rutaecarpine
Kraus, George A.,Guo, Haitao
scheme or table, p. 5337 - 5341 (2009/11/30)
(Chemical Equation Presented) The reaction of substituted (2-aminobenzyl)triphenylphosphonium bromides with aromatic aldehydes or α,β-unsaturated aldehydes constitutes a new synthesis of 2,3-disubstitued indoles in high yields. The adduct from 4-oxo-3,4- dihydroquinazoline-2-carbaldehyde was an advanced intermediate in the synthesis of several rutaecarpines.
