802280-14-4Relevant academic research and scientific papers
DMSO/SOCl2-mediated C(sp2)-H amination: Switchable synthesis of 3-unsubstituted indole and 3-methylthioindole derivatives
Zhang, Jingran,Li, Xiaoxian,Li, Xuemin,Shi, Haofeng,Sun, Fengxia,Du, Yunfei
supporting information, p. 460 - 463 (2021/01/25)
The reaction of 2-alkenylanilines with SOCl2 in DMSO was found to selectively afford 3-unsubstituted indoles and 3-methylthioindoles. This switchable approach was found to be temperature-dependent: at room temperature, the reaction afforded 3-unsubstituted indoles through intramolecular cyclization and elimination; while at higher temperature, the reaction gave 3-methylthioindoles via further electrophilic methylthiolation.
Divergent Syntheses of Indoles and Quinolines Involving N1-C2-C3 Bond Formation through Two Distinct Pd Catalyses
San Jang, Su,Kim, Young Ho,Youn, So Won
supporting information, p. 9151 - 9157 (2020/11/03)
Pd-catalyzed annulative couplings of 2-alkenylanilines with aldehydes using alcohols as both the solvent and hydrogen source have been developed. These domino processes allow divergent syntheses of two significant N-heterocycles, indoles and quinolines, from the same substrate by tuning reaction parameters, which seems to invoke two distinct mechanisms. The nature of the ligand and alcoholic solvent had a profound influence on the selectivity and efficiency of these protocols. Particularly noteworthy is that indole formation was achieved by overcoming two significant challenges, regioselective hydropalladation of alkenes and subsequent reactions between the resulting Csp3-Pd species and less reactive imines.
Metal-Free Activation of DMF by Dioxygen: A Cascade Multiple-Bond-Formation Reaction to Synthesize 3-Acylindoles from 2-Alkenylanilines
Wang, Ji-Bo,Li, Yin-Long,Deng, Jun
supporting information, p. 3460 - 3467 (2017/10/09)
A cascade C?N, C?C and C?O multiple-bond-formation reaction to synthesize 3-acylindoles from 2-alkenylanilines with DMF (N,N-dimethylformamide) as a one-carbon synthon is described. This approach employed dioxygen as a terminal oxidant and oxygen donor, generally provided the 3-acylindoles in moderate to good yields. Moreover, the mechanistic investigation unambiguously revealed that the 2-carbon of 3-acylindole was derived from the N-methyl group of DMF. (Figure presented.).
Bi(OTf)3-mediated intramolecular hydroamination of 2-aminostilbenes for the synthesis of 2-arylindolines
Youn, So Won,Jang, Su San,Lee, So Ra
, p. 4902 - 4909 (2016/07/18)
An efficient Bi(OTf)3-mediated intramolecular hydroamination of 2-aminostilbenes for the synthesis of various 2-arylindolines has been developed. Various advantages using Bi(OTf)3as a catalyst, such as the operationally easy, simple, and safe procedure, good to excellent chemical yields, and the use of relatively low catalyst loading are noteworthy.
Styrylphenylphthalimides as Novel Transrepression-Selective Liver X Receptor (LXR) Modulators
Nomura, Sayaka,Endo-Umeda, Kaori,Aoyama, Atsushi,Makishima, Makoto,Hashimoto, Yuichi,Ishikawa, Minoru
supporting information, p. 902 - 907 (2015/08/24)
Anti-inflammatory effects of liver X receptor (LXR) ligands are thought to be largely due to LXR-mediated transrepression, whereas side effects are caused by activation of LXR-responsive gene expression (transactivation). Therefore, selective LXR modulators that preferentially exhibit transrepression activity should exhibit anti-inflammatory properties with fewer side effects. Here, we synthesized a series of styrylphenylphthalimide analogues and evaluated their structure-activity relationships focusing on LXRs-transactivating-agonistic/antagonistic activities and transrepressional activity. Among the compounds examined, 17l showed potent LXR-transrepressional activity with high selectivity over transactivating activity and did not show characteristic side effects of LXR-transactivating agonists in cells. This representative compound, 17l, was confirmed to have LXR-dependent transrepressional activity and to bind directly to LXRβ. Compound 17l should be useful not only as a chemical tool for studying the biological functions of LXRs transrepression but also as a candidate for a safer agent to treat inflammatory diseases.
Rhodium(III)-catalyzed in situ oxidizing directing group- assisted c-h bond activation and olefination: A route to 2-vinylanilines
Muralirajan, Krishnamoorthy,Haridharan, Radhakrishnan,Prakash, Sekar,Cheng, Chien-Hong
, p. 761 - 766 (2015/03/18)
A new and efficient method for the synthesis of 2-vinylanilines from the reaction of arylhydrazine hydrochlorides with alkenes and diethyl ketone via a rhodium-catalyzed C-H activation is described. The oxidant-free olefination reaction involves the in situ generation of an -N-N=CR1R2 moiety as the oxidizing directing group thus providing an easy access to 2-vinylanilines.
Metal-free C-H amination for indole synthesis
Jang, Young Ho,Youn, So Won
supporting information, p. 3720 - 3723 (2014/08/05)
An effective metal-free C-H amination of N-Ts-2-alkenylanilines by using DDQ as an oxidant has been developed to afford a diverse range of substituted indoles. This protocol is operationally simple and robust, obviates the need of expensive transition-metal catalysts, and offers a broad substrate scope. A mechanism involving a radical cation generated by SET and a migratorial process via a phenonium ion intermediate is proposed.
