107734-14-5Relevant academic research and scientific papers
Preparation of 6-chloro-5-fluoroindole via the use of palladium and copper-mediated heterocyclisations
Adams, David R.,Duncton, Matthew A.J.,Roffey, Jonathan R.A.,Spencer, John
, p. 7581 - 7583 (2002)
The title indole, the heterocyclic core of the 5-HT2C receptor agonist Ro 60-0175, was prepared by a modification to the Stille indole synthesis, or by the method of Gonzalez and co-workers.
Carbamato-benzylidene ruthenium chelates – Synthesis, structure and catalytic activity in olefin metathesis
Rogalski, Szymon,?ak, Patrycja,Pawlu?, Piotr,Kubicki, Maciej,Pietraszuk, Cezary
, p. 1 - 9 (2018)
New carbamato-κN-benzylidene ruthenium chelates were synthesized from the first [RuCl2(PCy3)2(=CHPh)] and second [RuCl2(SIMes)(PCy3)(=CHPh)] generation Grubbs catalysts by metathetic exchange of benzylidene ligand for tert-butyl (2-vinylphenyl)carbamates bearing benzylidene ligand substituted in the position para to carbamato functionality with methyl or trifluoromethyl group. In all metathetical transformations tested, i.e. in ROMP of cycloocta-1,5-diene, RCM of diethyl diallylmalonate and diethyl 2-allyl-2-(2-methylallyl)malonate and cross-metathesis of allylbenzene with Z-1,4-diacetoxybut-2-ene, the complexes behave like latent catalysts. Complexes remain completely inactive until they are activated by the addition of ethereal solution of HCl. The presence of the electron-withdrawing group results in a slight increase in the catalytic activity of the activated form of the catalyst relative to a similar form of the unsubstituted complex or the least active complex carrying the electron donating group.
Electrochemical-mediated fixation of CO2: three-component synthesis of carbamate compounds from CO2, amines andN-alkenylsulfonamides
Liang, Ying,Pan, Ying-Ming,Tang, Hai-Tao,Xiong, Ting-Kai,Zhang, Min,Zhou, Xue-Qi
supporting information, p. 4328 - 4332 (2021/06/30)
An electrocatalyzed three-component cascade reaction of CO2, amines, andN-alkenylsulfonamides is developed, providing an environmentally friendly and efficient method of synthesizing a series of new carbamate compounds. This reaction meets the needs of green chemistry and promotes the participation of carbon dioxide in the three-component reaction by electro-oxidation. Pharmacological activity studies further prove that carbamate compounds have better activity than diamination by-products.
Direct Synthesis of Structurally Divergent Indole Alkaloids from Simple Chemicals
Shen, Tao,Zhu, Bencong,Lin, Fengguirong,Pan, Jun,Wei, Jialiang,Luo, Xiao,Liu, Jianzhong,Jiao, Ning
supporting information, p. 815 - 818 (2018/07/31)
A direct and structurally divergent synthesis of indole alkaloids from very simple 2-vinylanilines, alkynes and TBN via a novel substrate fragmentation/cycloaddition strategy has been developed, which provides an efficient noble-metal-free approach to access a library of highly valuable indole derivatives of tryptamines and tryptamine-related oximes, lactams, and lactones, as well as β-carbolines, spiroindolines, and hexa-hydropyrrolo[2,3-b]indoles.
Direct Tryptophols Synthesis from 2-Vinylanilines and Alkynes via C - C Triple Bond Cleavage and Dioxygen Activation
Shen, Tao,Zhang, Yiqun,Liang, Yu-Feng,Jiao, Ning
supporting information, p. 13147 - 13150 (2016/10/24)
An unexpected metal-free C - C triple bond cleavage, dioxygen activation, and reassembly into tryptophol derivatives has been developed. This chemistry provides a novel, simple, and efficient approach to highly valuable tryptophol derivatives from simple substrates under mild conditions. The mechanistic studies may promote the discovery of new methodologies through C-C bond cleavage and dioxygen activation.
Design, synthesis, and biological evaluation of novel transrepression- selective liver X receptor (LXR) ligands with 5,11-dihydro-5-methyl-11- methylene-6 H-dibenz[ b, e ]azepin-6-one skeleton
Aoyama, Atsushi,Endo-Umeda, Kaori,Kishida, Kenji,Ohgane, Kenji,Noguchi-Yachide, Tomomi,Aoyama, Hiroshi,Ishikawa, Minoru,Miyachi, Hiroyuki,Makishima, Makoto,Hashimoto, Yuichi
, p. 7360 - 7377 (2012/11/07)
To obtain novel transrepression-selective liver X receptor (LXR) ligands, we adopted a strategy of reducing the transactivational agonistic activity of the 5,11-dihydro-5-methyl-11-methylene-6H-dibenz[b,e]azepin-6-one derivative 10, which exhibits LXR-mediated transrepressional and transactivational activity. Structural modification of 10 based on the reported X-ray crystal structure of the LXR ligand-binding domain led to a series of compounds, of which almost all exhibited transrepressional activity at 1 or 10 μM but showed no transactivational activity even at 30 μM. Among the compounds obtained, 18 and 22 were confirmed to have LXR-dependent transrepressional activity by using peritoneal macrophages from wild-type and LXR-null mice. A newly developed fluorescence polarization assay indicated that they bind directly to LXRα. Next, further structural modification was performed with the guidance of docking simulations with LXRα, focusing on enhancing the binding of the ligands with LXRα through the introduction of substituents or heteroatom(s). Among the compounds synthesized, compound 48, bearing a hydroxyl group, showed potent, selective, and dose-dependent transrepressional activity.
Rhodium-catalyzed tandem conjugate addition-Mannich cyclization reaction: Straightforward access to fully substituted tetrahydroquinolines
So, Won Youn,Song, Ju-Hyun,Jung, Dai-Il
, p. 5658 - 5661 (2008/12/21)
(Chemical Equation Presented) A new Rh(I)-catalyzed tandem conjugate addition-Mannich cyclization reaction of imine-substituted electron-deficient alkenes with arylboronic acids has been developed to afford 2,3,4-trisubstituted 1,2,3,4-tetrahydroquinolines. This is the first example involving imine group as a secondary electrophile in Rh(I)-catalyzed tandem reactions.
Novel synthesis of 2-chloroquinolines from 2-vinylanilines in nitrile solvent
Lee, Byoung Se,Lee, Jae Hak,Chi, Dae Yoon
, p. 7884 - 7886 (2007/10/03)
2-Vinyl- or heteroaryl-substituted anilines were reacted with diphosgene in acetonitrile solution via a reactive imidoyl moiety to afford the corresponding 2-chloroquinolines. Facile syntheses of nine 2-chloroquinoline derivatives from several anilines and their postulate mechanism is described. The postulate mechanism of 2-chloroquinoline formation via imidoyl moiety as a good leaving group shows that the reaction consists of the following three steps: (1) generation of phenylisocyanate, (2) quinoline ring formation, and (3) chlorination on C2 position of quinoline.
Ortho-Vinylation reaction of anilines
Yamaguchi, Masahiko,Arisawa, Mieko,Hirama, Masahiro
, p. 1399 - 1400 (2007/10/03)
N-Alkylanilines and anilines are vinylated at the ortho-position with ethyne in the presence of SnCl4-Bu3N.
