823809-34-3Relevant 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
, 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.
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.
Silver(I)-mediated C-H amination of 2-alkenylanilines: Unique solvent-dependent migratory aptitude
Youn, So Won,Ko, Tae Yun,Jang, Min Jung,Jang, Su San
supporting information, p. 227 - 234 (2015/01/30)
A highly effective silver(I)-mediated C-H amination of 2-alkenylanilines has been developed to afford a diverse range of substituted indoles. High functional group tolerance, broad substrate scope, simple/fast/high-yielding reaction, and recovery/reuse of the inexpensive silver oxidant are noteworthy. Furthermore, an uncommon migratory process of β-monosubstituted 2-alkenylanilines with solvent-dependence was demonstrated.
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.
Synthesis and photochemistry of 3-(o-stilbeneyl)-4-H/Me/Ph-sydnones; Intramolecular cyclization to 1,2-benzodiazepines and/or quinolines
Butkovi?, Kristina,Vuk, Dragana,Marini?, ?eljko,Peni?, Josip,?indler-Kulyk, Marija
experimental part, p. 9356 - 9362 (2011/01/12)
Stilbeneylsydnone derivatives were synthesized by a sequence of reactions in good yields. Irradiation of 3-stilbeneyl-4-methylsydnone 4 gives 1H-1,2-benzodiazepine derivative 7 as the main product along with 2-methylquinoline derivative 20. Irradiation of 3-stilbeneyl-4-phenylsydnone 5 afforded only 1H-1,2-benzodiazepine derivative 8 whereas on irradiation of 4-unsubstituted 3-stilbeneylsydnone 3 no benzodiazepine derivative was detected. An efficient novel photochemical approach to 1H-1,2-benzodiazepines has been found from the new 3-(o-stilbeneyl)-4-substituted-sydnones via intramolecular 1,7-electrocyclization reaction of the photogenerated nitrile imines.
Dirhodium(II)-catalyzed intramolecular C-H amination of aryl azides
Shen, Meihua,Leslie, Brooke E.,Driver, Tom G.
supporting information; experimental part, p. 5056 - 5059 (2009/03/11)
(Chemical Equation Presented) Azides to indoles: Dirhodium(II)-catalyzed decomposition of aryl azides was developed as a mild, functional group tolerant method for the synthesis of indoles (see scheme).
Complete 1H and 13C NMR spectral assignment of cis- and trans- 3-{2-[2-(4-methylphenyl)ethenyl]phenyl}sydnones
Butkovic, Kristina,Marinic, Zeljko,Sindler-Kulyk, Marija
, p. 1053 - 1055 (2007/10/03)
1H and 13C NMR spectra of cis- and trans-3-{2-[2-(4-methylphenyl)ethenyl]phenyl]}sydnones, the first stilbene-substituted mezoionic oxadiazolium rings, were fully assigned combining the information in various solvents, such as deuter
