100717-32-6Relevant articles and documents
Highly diastereoselective oxa-[3+3] cyclization with C,N-cyclic azomethine imines: Via the copper-catalyzed aerobic oxygenated CC bond of indoles
Yu, Lemao,Zhong, Yuan,Yu, Jicong,Gan, Lu,Cai, Zhengjun,Wang, Rui,Jiang, Xianxing
, p. 2353 - 2356 (2018)
Herein, a copper-catalyzed highly diastereoselective aerobic oxygenated [3+3] cyclization of 3-substituted indoles with C,N-cyclic azomethine imines using oxygen as the sole oxidant under mild conditions has been developed. This protocol provides a simple and convenient approach for constructing [2,3]-fused indoline O-heterocycles bearing two pharmaceutically intriguing parts, tetrahydroisoquinoline and indoline. Good yields and excellent diastereoselectivity under mild reaction conditions were observed.
Annulative π-Extension (APEX) of Indoles to Pyrido[1,2- a]indoles Using 4-Oxo Peroxides as C4 Units
Wang, Xin,Lou, Chenhao,Lv, Leiyang,Li, Zhiping
, p. 5978 - 5982 (2021)
Annulative π-extension (APEX) of 3-substituted indoles to pyrido[1,2-a]indoles is developed by using 4-oxo peroxides as π-extending reagents, which are employed as versatile C4 building blocks. This transformation is initiated by Br?nsted acid-mediated Hock rearrangement of the peroxyl group. Notably, the pyrido[1,2-a]indole products are obtained by elimination of the indole moiety from the corresponding dihydropyrido[1,2-a]indoles, which could be selectively formed at room temperature.
Transition-Metal-Catalyzed Regioselective Alkylation of Indoles with Alcohols
Putra, Anggi Eka,Takigawa, Kei,Tanaka, Hatsuki,Ito, Yoshihiko,Oe, Yohei,Ohta, Tetsuo
, p. 6344 - 6354 (2013)
The regioselective alkylation of indoles with alcohols as alkylating reagents was developed by using Pd/C or RuCl2(PPh3) 3/DPEphos {DPEphos = bis[(2-diphenylphosphanyl)phenyl] ether}as catalysts. The reaction of indole with benzyl alcohol in the presence of Pd/C and K2CO3 at 80 °C for 24 h without any solvent under in air yielded 90 % of 3-benzylindole. The corresponding 3-benzylindole was obtained in 99 % yield when the reaction was catalyzed by RuCl 2(PPh3)3/DPEphos in the presence of K 3PO4 at 165 °C for 24 h under argon. Several types of alcohols were treated with indoles under these conditions to give the corresponding 3-alkylated indoles in high yields (up to 99 %). This reaction may involve the catalyst-mediated transformation of alcohols to aldehydes, nucleophilic addition of indole to the resulting aldehydes accompanied by dehydration, and then hydrogenation. Copyright
Ruthenium Pincer Complex Catalyzed Selective Synthesis of C-3 Alkylated Indoles and Bisindolylmethanes Directly from Indoles and Alcohols
Biswas, Nandita,Sharma, Rahul,Srimani, Dipankar
supporting information, p. 2902 - 2910 (2020/06/03)
Herein, we presented Ru-SNS complex that serves as a useful catalyst for C-3 alkylation of 1H-indoles with various aliphatic primary and secondary alcohols including cyclic alcohols as well as benzylic alcohols. The selective synthesis of bisindolylmethane derivatives is also achieved from the same set of indole and alcohol just by altering the reaction parameters. Furthermore, the sustainable synthesis of C-3 alkylated indoles directly from 2-(2-nitrophenyl)ethan-1-ol and alcohols catalysed by a Ru-complex via “borrowing hydrogen” strategy is reported. This protocol provides an atom-economical sustainable route to access structurally important compounds like arundine, vibrindole A and tryptamine based derivatives. (Figure presented.).
