1722-07-2Relevant academic research and scientific papers
Solid-phase synthesis of diverse tetrahydro-1,4-benzodiazepine-2-ones
Bhalay, Gurdip,Blaney, Paul,Palmer, Vanessa H.,Baxter, Anthony D.
, p. 8375 - 8378 (1997)
A general method for the construction of tetrahydro-1,4-benzodiazepine- 2-ones on solid-support has been developed utilising a cleavage-conjugate addition protocol as the key step in the design. Using this novel, methodology the synthesis of a diverse one
Phosphine-Catalyzed Reaction between 2-Aminobenzaldehydes and Dialkyl Acetylenedicarboxylates: Synthesis of 1,2-Dihydroquinoline Derivatives and Toward the Development of an Olefination Reaction
Han, Xu,Saleh, Nidal,Retailleau, Pascal,Voituriez, Arnaud
supporting information, p. 4584 - 4588 (2018/08/09)
A series of 1,2-dihydroquinolines were synthesized in good to excellent yields by reacting 2-aminobenzaldehyde derivatives and dialkyl acetylenedicarboxylates with catalytic amounts of phosphine. This reaction was rendered catalytic by the selective in situ phosphine oxide reduction with the use of phenylsilane. Furthermore, with the same starting materials and with an additional role of the reducing agent, a new olefination reaction was discovered. Hydrogen/deuterium (H/D) exchange experiments revealed the possible mechanism of this reaction.
Sunlight-Driven Forging of Amide/Ester Bonds from Three Independent Components: An Approach to Carbamates
Zhao, Yating,Huang, Binbin,Yang, Chao,Chen, Qingqing,Xia, Wujiong
, p. 5572 - 5575 (2016/11/17)
A photoredox catalytic route to carbamates enabled by visible irradiation (or simply sunlight) has been developed. This process leads to a novel approach to the construction of heterocyclic rings wherein the amide or ester motifs of carbamates were assembled from three isolated components. Large-scale experiments were realized by employing continuous flow techniques, and reuse of photocatalyst demonstrated the green and sustainable aspects of this method.
Application of daugulis copper-catalyzed direct arylation to the synthesis of 5-aryl benzotriazepines
Yotphan, Sirilata,Bergman, Robert G.,Ellman, Jonathan A.
supporting information; experimental part, p. 1511 - 1514 (2009/08/07)
A method for the direct arylation of benzotriazepines is reported, employing an aryl iodide as the coupling partner, copper iodide as the catalyst, and lithium tert-butoxide as the base. A variety of electron-rich, electron-poor, and sterically hindered aryl iodides are compatible with the reaction conditions. The arylation reaction can also be performed outside a glovebox in air without a significant decrease in yield. Furthermore, convenient microwave conditions for carrying out this transformation are reported.
Selective mono-N-alkylation of 3-amino alcohols via chelation to 9-BBN
Bar-Haim, Galia,Kol, Moshe
, p. 3549 - 3551 (2007/10/03)
(Chemical Equation Presented) A method for selective mono-N-alkylation of amino alcohols is introduced. This method relies on formation of a stable chelate with 9-BBN, which serves in the dual roles of protecting and activating the amine group. Three prot
Copper-catalyzed formation of carbon-heteroatom and carbon-carbon bonds
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, (2015/03/06)
The present invention relates to copper-catalyzed carbon-heteroatom and carbon-carbon bond-forming methods. In certain embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between the nitrogen atom of an amide or amine moiety and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In additional embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between a nitrogen atom of an acyl hydrazine and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In other embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between the nitrogen atom of a nitrogen-containing heteroaromatic, e.g., indole, pyrazole, and indazole, and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In certain embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-oxygen bond between the oxygen atom of an alcohol and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. The present invention also relates to copper-catalyzed methods of forming a carbon-carbon bond between a reactant comprising a nucleophilic carbon atom, e.g., an enolate or malonate anion, and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. Importantly, all the methods of the present invention are relatively inexpensive to practice due to the low cost of the copper comprised by the catalysts.
Copper-catalyzed coupling of alkylamines and aryl iodides: an efficient system even in an air atmosphere.
Kwong, Fuk Yee,Klapars, Artis,Buchwald, Stephen L
, p. 581 - 584 (2007/10/03)
[reaction: see text] A mild method for the copper-catalyzed amination of aryl iodides is reported. This operationally simple C-N bond-forming protocol uses CuI as the catalyst and ethylene glycol as ligand in 2-propanol. A variety of functionalized aryl iodides as well as several amines were efficiently coupled using this method. This catalytic amination procedure is relatively insensitive to moisture and can be performed under an air atmosphere with comparable yield. Preliminary results on the amination of aryl bromides are also described.
Synthesis and structure-activity relationship of 2-(aminoalkyl)-2,3,3a,8-tetrahydrodibenzo[c,f]isoxazolo[2,3-a]azepine derivatives: A novel series of 5-HT2A/2C receptor antagonists. Part 1
Andres,Alcazar, Jesus,Alonso, Jose M.,Diaz, Adolfo,Fernandez, Javier,Gil, Pilar,Iturrino, Laura,Matesanz, Encarna,Meert, Theo F.,Megens, Anton,Sipido, Victor K.
, p. 243 - 248 (2007/10/03)
The synthesis of a series of novel 2-(aminoalkyl)-2,3,3a,8-tetrahydrodibenzo[c,f]isoxazolo[2,3-a]azepine derivatives as well as their 5-HT2A/2C and H1 receptor binding affinities are described. The in vivo activity as potential anxiolytics of the synthesised compounds was measured in a mCPP challenge test. One of the compounds, 2a, proved to be a potent 5-HT2A/2C receptor antagonist showing as well oral activity and therefore could be considered as a potential anxiolytic/antidepressant agent.
Synthesis and structure-activity relationships of N-substituted 2-[(2-imidazolylsulfinyl)methyl]anilines as a new class of gastric H+/K+-ATPase inhibitors
Yamakawa,Matsukura,Nomura,Yoshioka,Masaki,Igata,Okabe
, p. 1746 - 1752 (2007/10/02)
A series of N-substituted 2-[(2-imidazolylsulfinyl)methyl]anilines was synthesized and evaluated for its biological activity against H+/K+-ATPase prepared from rabbit stomach and gastric acid secretions in Heidenhain pouch dogs. Monoalkyl substituents on the nitrogen atom of the aniline moiety markedly inhibited the enzyme activity to the same degree as omeprazole, a representative H+/K+-ATPase inhibitor. Most of these compounds, administered at 3 mg/kg i.v. inhibited histamine-stimulated gastric acid secretion. The inhibitory activity of these derivatives on the enzymes at pH 6.0 was more potent than that at pH 7.4, and was distinctly correlated to stability in aqueous solution at pH 5.0.
