67987-45-5Relevant academic research and scientific papers
Lithium-Promoted Cycloaddition of Indole-2,3-dienolates and Carbon Disulfide as a One-Pot Route to Thiopyrano[4,3- b]indole-3(5 H)-thiones
Suzdalev, Konstantin F.,Vyalyh, Julia V.,Tkachev, Valery V.,Lysenko, Ekaterina A.,Burov, Oleg N.,Lisovin, Anton V.,Kletskii, Mikhail E.,Kurbatov, Sergey V.
, p. 11698 - 11707 (2021)
A new approach for the annulation of a thiopyrane ring to an indole core under mild conditions was developed. Treating 2-methyl-3-acylindoles with lithium diisopropyl amide leads to the elimination of a proton from the 2-methyl group. The lithium indole-2,3-dienolates obtained were found to react with CS2 to give the corresponding thiopyrano[4,3-b]indole-3(5H)-thiones. The mechanism represents a stepwise addition through ion-pair formation, according to PCM/B3LYP/6-311++G**, PBE1PBE/6-311++G**, and MP2//HF/6-311++G*? quantum chemical calculations. AIM calculations revealed the essential role of the Li atom at all stages of the process.
Synthesis of diaryl ketones through oxidative cleavage of the C-C double bonds in N -Sulfonyl enamides
Kim, Hyunseok,Park, Sangjune,Baek, Yonghyeon,Um, Kyusik,Han, Gi Uk,Jeon, Da-Hye,Han, Sang Hoon,Lee, Phil Ho
, p. 3486 - 3496 (2018/04/14)
An oxidative cleavage of a C-C double bond is developed from the photochemical [2+2]-cycloaddition of diaryl N-tosyl enamides, aryl heteroaryl N-tosyl enamides, and N-tosyl cyclic enamides with singlet molecular oxygen, followed by a ring-opening reaction mediated by Cs2CO3 under air and sunlight without the use of photosesitizer, producing symmetrical and unsymmetrical diaryl, heterodiaryl, and cyclic ketones in good to excellent yields. Moreover, the oxidative cleavage of C-C triple bonds from 1-alkynes is demonstrated for the synthesis of symmetrical and unsymmetrical ketones from the Cu-catalyzed [3+2]-cycloaddition, Rh-catalyzed alkoxyarylation, photooxygenation, and ring-opening reaction in one-pot. Because the synthesis of the symmetrical and unsymmetrical diaryl and/or heterodiaryl ketones bearing an electron-donating group is not easy, the present method is notable.
3-Acylindoles Synthesis: Ruthenium-Catalyzed Carbonylative Coupling of Indoles and Aryl Iodides
Wang, Zechao,Yin, Zhiping,Wu, Xiao-Feng
supporting information, p. 4680 - 4683 (2017/09/12)
A novel and convenient procedure for the synthesis of 3-acylindoles from simple indoles and aryl iodides has been established. Through ruthenium-catalyzed carbonylative C-H functionalization of indoles, with Mo(CO)6 as the solid CO source, the desired indol-3-yl aryl ketones were isolated in moderate to good yields. Not only N-alkylindoles but also N-H indoles can be applied here.
