24310-30-3Relevant academic research and scientific papers
Anion-π interaction augments halide binding in solution
Berryman, Orion B.,Hof, Fraser,Hynes, Michael J.,Johnson, Darren W.
, p. 506 - 508 (2006)
1H NMR spectroscopic data and complementary theoretical predictions suggest that a designed receptor exhibits the anion-π interaction in solution. The Royal Society of Chemistry 2006.
Electrochemical Palladium-Catalyzed Intramolecular C—H Amination of 2-Amidobiaryls for Synthesis of Carbazoles
Gao, Xinlong,Lei, Aiwen,Wang, Pan,Wang, Qingqing,Zhang, Heng,Zhang, Xiaojing
, p. 143 - 148 (2020/12/18)
The synthesis of carbazoles based on the electrochemical Pd-catalyzed intramolecular C—H amination of 2-amidobiaryls through oxidative cross coupling has been achieved under mild reaction conditions. The reaction can be carried out in undivided cell without the addition of external chemical oxidant. Besides good functional group compatibility, the desired carbazoles can be scaled up and modified easily. Compared with previous methods, this protocol affords a simple and sustainable avenue for the construction of carbazoles.
Catalytic Synthesis of Dibenzazepines and Dibenzazocines by 7-Exo- and 8-Endo-Dig-Selective Cycloisomerization
Ito, Mamoru,Takaki, Asahi,Okamura, Moeka,Kanyiva, Kyalo Stephen,Shibata, Takanori
, p. 1688 - 1692 (2021/03/22)
The 7-exo- and 8-endo-dig-selective gold-catalyzed cycloisomerizations of 2-propargylamino biphenyl derivatives were developed. The reaction of terminal alkynes gave dibenzo[b,d]azepines by 7-exo-dig cycloisomerization. In contrast, when internal alkynes were subjected to the reaction, 8-endo-dig cycloisomerization proceeded to provide dibenzo[b,d]azocines. The nucleophilicity at the reaction site and the electron-withdrawing effect of a tosyl group were important for the present selective transformation. This protocol could be used for ynamide substrates and a silver-catalyzed reaction gave 7-exo-dig products selectively.
Atropisomeric Properties of N-Acyl/ N-Sulfonyl 5 H-Dibenzo[ b, d]azepin-7(6 H)-ones
Hotta, Mayuno,Makino, Kosho,Namba, Takuya,Natsugari, Hideaki,Oshitari, Tetsuta,Tabata, Hidetsugu,Takahashi, Hideyo
supporting information, p. 7563 - 7578 (2021/06/25)
The stereochemistry of N-acyl/N-sulfonyl 5H-dibenzo[b,d]azepin-7(6H)-ones (I, II) was examined in detail by freezing the conformation with a methyl group at the C-4 of dibenzoazepine. Because the two axes (axis 1, axis 2) move together concertedly, I and
Preparation method of carbazole compound
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Paragraph 0029-0030, (2020/08/17)
The invention relates to a preparation method of a carbazole compound. The method comprises the following steps: adding a reaction substrate as shown in a formula (III) into a solvent for dissolving,adding cyclic diacyl peroxide and transition metal, and
One-pot Cascade Reaction for the Synthesis of Phenanthridines via Suzuki Coupling/C?H Oxidation/Aromatization
Chen, Rener,Ding, Yuxin,Ma, Yongmin,Zhang, Yi
, p. 5697 - 5707 (2020/12/01)
A one-pot cascade coupling/annulation reaction for the synthesis of phenanthridines has been developed from arylboronic acids and o-bromo arylamides with DMSO as a carbon source. The desired phenanthridines were obtained in moderate to good yields by using simple procedure. (Figure presented.).
Triple Mode of Alkylation with Ethyl Bromodifluoroacetate: N, or O-Difluoromethylation, N-Ethylation and S-(ethoxycarbonyl)difluoromethylation
Polley, Arghya,Bairy, Gurupada,Das, Pritha,Jana, Ranjan
supporting information, p. 4161 - 4167 (2018/09/21)
In this report, we have explored a triple mode of chemical reactivity of ethyl bromodifluoroacetate. Typically, bromodifluoroacetic acid has been used as a difluorocarbene precursor for difluoromethylation of soft nucleophiles. Here we have disclosed nucleophilicity and base dependent divergent chemical reactivity of ethyl bromodifluoroacetate. It furnishes lithium hydroxide and cesium carbonate promoted difluoromethylation of tosyl-protected aniline and electron-deficient phenols respectively. Interestingly, switching the base from lithium hydroxide to 4-N,N-dimethylamino pyridine (DMAP) tosyl-protected anilines afforded the corresponding N-ethylation product. Whereas, highly nucleophilic thiophenols furnished the corresponding S-carboethoxydifluoromethylation product via a rapid SN2 attack to the bromine atom prior to the ester hydrolysis. This mechanistic divergence was established through several control experiments. It was revealed that difluoromethylation reaction proceeds through a tandem in situ ester hydrolysis/decarboxylative-debrominative difluorocarbene formation and subsequent trapping by the soft nucleophile-NHTs or electron-deficient phenolic ?OH groups. In the presence of DMAP the hydrolysis of the ester is perturbed instead a nucleophilic attack at the ethyl moiety provides the N-ethylation product. Hence, besides the development of a practical base-promoted N-difluoromethylation of amines and electron-deficient phenols, divergent reactivity pattern of inexpensive and user-friendly ethyl bromodifluoroacetate has been explored. (Figure presented.).
Diastereoselective Synthesis of Dibenzo[b,d]azepines by Pd(II)-Catalyzed [5 + 2] Annulation of o-Arylanilines with Dienes
Bai, Lu,Wang, Yan,Ge, Yicong,Liu, Jingjing,Luan, Xinjun
supporting information, p. 1734 - 1737 (2017/04/11)
An efficient method for the construction of dibenzo[b,d]azepines containing two distinct stereogenic elements in a highly diastereoselective fashion is described. The key of the [5 + 2] reaction is to form a π-allylpalladium species through sequential C-H
Flow synthesis and biological activity of aryl sulfonamides as selective carbonic anhydrase IX and XII inhibitors
Rosatelli, Emiliano,Carotti, Andrea,Ceruso, Mariangela,Supuran, Claudiu T.,Gioiello, Antimo
supporting information, p. 3422 - 3425 (2014/07/22)
A series of secondary and tertiary aryl sulfonamides were synthesized under flow conditions and evaluated for their ability to selectively inhibit tumor-associated carbonic anhydrase isoforms IX and XII. The tested compounds revealed to be highly potent CA IX inhibitors in nanomolar range, and to inhibit CA XII activity with different ranks of potencies. Remarkably, 4-methyl-N-phenyl-benzenesulfonamide was a selective nanomolar CA IX inhibitor with an IC50 of 90 nM.
Palladium-catalyzed intramolecular oxidative coupling involving double C(sp2)-H bonds for the synthesis of annulated biaryl sultams
Laha, Joydev K.,Jethava, Krupal P.,Dayal, Neetu
, p. 8010 - 8019 (2015/03/18)
The palladium-catalyzed intramolecular oxidative coupling described herein involves a double C(sp2)-H bond functionalization in sulfonanilides, providing a workable access to biaryl sultams annulated into a six-membered ring that are otherwise difficult to obtain by literature methods. The other synthetic applications of this protocol including the synthesis of biaryl sultams containing a seven-membered ring and analogous sultones are also presented.
