1496-76-0Relevant articles and documents
Selective N1-Acylation of Indazoles with Acid Anhydrides Using an Electrochemical Approach
DIssanayake, D.M.M. Mevan,Vannucci, Aaron K.
, p. 457 - 460 (2019)
An electrochemical synthesis method for the selective N1-acylation of indazoles has been developed. This "anion pool" approach electrochemically reduces indazole molecules generating indazole anions and H2. Acid anhydrides are then introduced to the solution resulting in selective acylation of the N1-position of the indazoles. This procedure can also be applied to the acylation of benzimidazoles and indoles. The reaction can also be performed using a 9 V battery without loss of reaction efficiency.
An effective C-C double bond formation via Cu(I)-catalyzed dehydrogenation
Ramirez, Thomas A.,Zhao, Baoguo,Shi, Yian
, p. 1822 - 1825 (2010)
A dehydrogenation method using Cu(I) and either N,N-di-tert-butylthiadiaziridine 1,1-dioxide or N,N-di-tert-butyldiaziridinone is reported. The dehydrogenation allows a facile introduction of C-C double bond(s) into various carbocycles and heterocycles such as oxazolines and thiazolines.
Na 2 CO 3-Catalyzed N-Acylation of Indoles with Alkenyl Carboxylates
Zhou, Xiao-Yu,Chen, Xia
, p. 516 - 521 (2019)
The N-acylation of indoles has been accomplished via inorganic base catalysis. It provided an efficient and simple catalysis system for the preparation of N-acylindoles with alkenyl carboxylates as acylating agents. A broad variety of indoles undergo the smooth N-acylation using Na 2 CO 3 as catalyst in MeCN at 120? °C to give the corresponding N-acylindoles in good to excellent yields.
Trifluoromethylselenolation andN-acylation of indoles with [Me4N][SeCF3]
Dong, Tao,Tan, Kai-Li,Wang, Hao-Nan,Zhang, Cheng-Pan
, p. 5368 - 5376 (2021)
An efficient method for oxidative trifluoromethylselenolation/N-acylation of indoles with excess [Me4N][SeCF3] in the presence of acyl peroxides and their derivatives is described. The reaction is easy to handle, proceeds smoothly at room temperature under metal-free conditions, and shows advantages such as good functional group tolerance, excellent regioselectivity, and compatibility of a number of substrates, producing 1-acyl and 3-trifluoromethylselanyl substituted indoles in good yields. Acyl peroxides and peroxycarboxylic acid behave as both oxidants and acyl sources in the transformation. This one-pot procedure provides a convenient access to a new class of indole derivatives, representing the first trifluoromethylselanyl bifunctionalization of indoles with the nucleophilic [Me4N][SeCF3] reagent.
Photoredox Catalysis Induced Bisindolylation of Ethers/Alcohols via Sequential C-H and C-O Bond Cleavage
Ye, Lu,Cai, Sai-Hu,Wang, Ding-Xing,Wang, Yi-Qiu,Lai, Lin-Jie,Feng, Chao,Loh, Teck-Peng
, p. 6164 - 6167 (2017)
A visible-light-engaged 2-fold site-selective alkylation of indole derivatives with aliphatic ethers or alcohols has been accomplished for easy access to symmetric 3,3′-bisindolylmethane derivatives. The experimental data suggest a sequential photoredox catalysis induced radical addition and proton-mediated Friedel-Crafts alkylation mechanism.
Scaffold hopping by net photochemical carbon deletion of azaarenes
Woo, Jisoo,Christian, Alec H.,Burgess, Samantha A.,Jiang, Yuan,Mansoor, Umar Faruk,Levin, Mark D.
, p. 527 - 532 (2022/05/10)
Discovery chemists routinely identify purpose-tailored molecules through an iterative structural optimization approach, but the preparation of each successive candidate in a compound series can rarely be conducted in a manner matching their thought process. This is because many of the necessary chemical transformations required to modify compound cores in a straightforward fashion are not applicable in complex contexts. We report a method that addresses one facet of this problem by allowing chemists to hop directly between chemically distinct heteroaromatic scaffolds. Specifically, we show that selective photolysis of quinoline N-oxides with 390-nanometer light followed by acid-promoted rearrangement affords N-acylindoles while showing broad compatibility with medicinally relevant functionality. Applications to late-stage skeletal modification of compounds of pharmaceutical interest and more complex transformations involving serial single-atom changes are demonstrated.
Organophosphane-Catalyzed Construction of Functionalized 2-Ylideneoxindoles via Direct β-Acylation
Jeng, Wey-Chyng,Chien, Po-Chung,Vagh, Sandip Sambhaji,Edukondalu, Athukuri,Lin, Wenwei
, p. 4409 - 4418 (2021/08/25)
We report an efficient method for the direct β-acylation of 2-ylideneoxindoles with acyl chlorides that is catalyzed by organophosphanes in the presence of base. A variety of functionalized 2-ylideneoxindoles were prepared in moderate to good yields under
