108665-95-8Relevant articles and documents
Synthesis of 2-nitroindoles via the Sundberg indole synthesis
Pelkey, Erin T.,Gribble, Gordon W.
, p. 5603 - 5606 (1997)
A three-step sequence has been developed for converting o-nitrobenzaldehydes into 2-nitroindoles. The key step involves the thermolysis of 2-(o-azidophenyl)nitroethylene (10) in xylenes which gives 2-nitroindole (4) in 54% yield, akin to the classic Sundberg indole synthesis. This procedure has also been utilized to synthesize 5,6-dimethoxy-2-nitroindole (14).
Multifunctionalization of Indoles: Synthesis of 3-Iodo-2-sulfonyl Indoles
Park, Hyowon,Bae, Junryeol,Son, Soobin,Jang, Hye-Young
supporting information, p. 1128 - 1133 (2019/11/22)
The selective multifunctionalization of indoles by using thiosulfonates, trimethyl sulfoxonium iodide (Me3SOI), and H2O2 was studied. The reaction of thiosulfonates with Me3SOI and H2O2 produced sulfonyl radicals and an iodination reagent, both of which were incorporated in indoles to form 3-iodo-2-sulfonyl indoles under carefully controlled conditions. The related reaction mechanism and the substrate scope of 3-iodo-2-sulfonyl indoles are presented.
A Sulfonylation Reaction: Direct Synthesis of 2-Sulfonylindoles from Sulfonyl Hydrazides and Indoles
Rahaman, Rajjakfur,Barman, Pranjit
supporting information, p. 684 - 690 (2017/03/21)
A metal-free synthesis of 2-sulfonylindole derivatives has been developed through a novel TBHP/I2-mediated coupling of C3/unsubstituted indoles with sulfonyl hydrazides. The reaction utilizes readily available starting materials under mild reaction conditions, providing an alternative and attractive approach to 2-sulfonylindoles with high yields. The developed synthetic procedure is suitable for both N-protected or unprotected indoles.
Convenient KI-catalyzed regioselective synthesis of 2-sulfonylindoles using water as solvent
Li, Hongjie,Wang, Xiaolong,Yan, Jie
supporting information, p. 4277 - 4280 (2017/07/11)
A convenient procedure is developed for the preparation of 2-sulfonylindoles from indoles and sodium sulfinates catalyzed by KI in water. This environmentally benign 2-sulfonylation of indoles proceeds efficiently under mild conditions, affording the products with high regioselectivity and in moderate to good yields.
Electrooxidative Metal-Free Dehydrogenative α-Sulfonylation of 1H-Indole with Sodium Sulfinates
Feng, Mei-Lin,Xi, Long-Yi,Chen, Shan-Yong,Yu, Xiao-Qi
, p. 2746 - 2750 (2017/05/29)
A method for the electrochemical α-sulfonylation of 1H-indole with arenesulfinates was developed. A variety of indoles underwent this sulfonylation smoothly at room temperature under metal-free and chemical-oxidant-free conditions to afford indolyl aryl sulfones in good to high yields. This reaction was found to tolerate a variety of functional groups, including halides and cyclopropyl, ether, ester, and aldehyde groups. It was applied to the synthesis of biologically active 5-HT6 modulators.
Iodine-catalyzed regioselective 2-sulfonylation of indoles with sodium sulfinates
Xiao, Fuhong,Chen, Hui,Xie, Hao,Chen, Shuqing,Yang, Luo,Deng, Guo-Jun
supporting information, p. 50 - 53 (2014/01/23)
Iodine-catalyzed selective 2-arylsulfonyl indole formation from indoles and sodium sulfinates is disclosed. Various substituted 2-arylsulfonyl indoles were obtained in one pot in the absence of metal catalyst at room temperature under air.
Regioselective C 2 sulfonylation of indoles mediated by molecular iodine
Katrun, Praewpan,Mueangkaew, Charoensak,Pohmakotr, Manat,Reutrakul, Vichai,Jaipetch, Thaworn,Soorukram, Darunee,Kuhakarn, Chutima
, p. 1778 - 1785 (2014/03/21)
A facile and general method for regioselective C2 sulfonylation reaction of indoles mediated by iodine is described. The 2-sulfonylated products were obtained up to 96% yield under mild reaction conditions (room temperature, 2 h).
ZnO-mediated regioselective C-arylsulfonylation of indoles: A facile solvent-free synthesis of 2- and 3-sulfonylindoles and preliminary evaluation of their activity against drug-resistant mutant HIV-1 reverse transcriptases (RTs)
Tocco, Graziella,Begala, Michela,Esposito, Francesca,Caboni, Pierluigi,Cannas, Valeria,Tramontano, Enzo
, p. 6237 - 6241 (2013/10/22)
A ZnO-mediated one-pot solvent-free protocol for the regioselective C-arylsulfonylation of indoles is described and some novel derivatives were tested on wild type and non-nucleoside inhibitor resistant K103N and Y181C HIV-1 reverse transcriptases (RTs).
1,2-Bis(phenylsulfonyl)-1H-indole as an acceptor of organocuprate nucleophiles
Qian, David C.,Alford, Philip E.,Kishbaugh, Tara L. S.,Jones, Sean T.,Gribble, Gordon W.
, p. 66 - 73 (2012/11/07)
1,2-Bis(phenylsulfonyl)-1H-indole is a novel example of an electron-deficient indole that undergoes nucleophilic attack at C-3. Though a variety of other organometallic nucleophiles fail to engender nucleophilic substitution, organocuprates produce 3-substituted 2-(phenylsulfonyl)-1H- indoles. These reactions contribute to the growing number of examples of nucleophilic addition to the indole core. ARKAT USA, Inc.
Nucleophilic addition reactions of 2-nitro-1-(phenylsulfonyl)indole. A new synthesis of 3-substituted-2-nitroindoles
Pelkey, Erin T.,Barden, Timothy C.,Gribble, Gordon W.
, p. 7615 - 7619 (2007/10/03)
2-Nitro-1-(phenylsulfonyl)indole (1) undergoes nucleophilic addition reactions with the enolates of diethyl malonate and cyclohexanone, lithium dimethylcuprate, and indole anion to afford the corresponding 3-substituted-2-nitroindoles (4-6,8,9) in low to high yields. Reaction of 1-(phenylsulfonyl)-2-(trialkylstannyl)indoles 13 and 14 with tetranitromethane affords the novel isoxazolo[5,4-b]indole 15 via a 1,3-dipolar cycloaddition reaction with in situ generated nitro formonitrile oxide (19).
