15224-25-6Relevant articles and documents
A general method for acylation of indoles at the 3-position with acyl chlorides in the presence of dialkylaluminum chloride.
Okauchi,Itonaga,Minami,Owa,Kitoh,Yoshino
, p. 1485 - 1487 (2000)
[reaction--see text] Indoles are selectively acylated at the 3-position in high yields on treatment with a wide variety of acyl chlorides in CH(2)Cl(2) in the presence of diethylaluminum chloride or dimethylaluminum chloride. The reaction proceeds under mild conditions and is applicable to indoles bearing various functional groups without NH protection.
The Reactions of Electron-Rich Heterocycles with Derivatives of Orthocarboxylic Acids; VIII. Proton Acid-Catalyzed Acylation of Indoles by 2-Alkoxy-1,3-dioxolanes
Akguen, Eyuep,Tunali, Mustafa,Pindur, Ulf
, p. 397 - 401 (1987)
In acid-catalyzed reactions with 3-unsubstituted indoles 1, 2-alkoxy-1,3-dioxolanes 2a-c behave as acyl equivalents.Depending on the substitution patterns of the reaction partners, the 1,3-dioxolanium ions 3a-c, generated in situ from the cyclic ortho esters by the action of sulfosalicylic acid, react to form tris-(3-indolyl)alkanes 6 and 9, bis-(3-indolyl)ethenes 7, or 3-benzoylindoles 8.Analogous reactivity was observed with related acyclic ortho esters.
A radical addition and cyclization relay promoted by Mn(OAc)3?2H2O: Synthesis of 1,2-oxaphospholoindoles and mechanistic study
Xu, Meng-Meng,Kou, Lu-Yao,Bao, Xiao-Guang,Xu, Xiao-Ping,Ji, Shun-Jun
supporting information, p. 1915 - 1919 (2021/03/09)
Novel and efficient Mn(OAc)3?2H2O promoted radical addition-[4 + 1] cyclization relay of 3-indolymethanols and phosphites was disclosed, which afforded 1,2-oxaphospholoindole derivatives in moderate to good yields. Based on the experimental and computational studies, a mechanism involving radical addition and intramolecular cyclization cascade was proposed.
NbCl5 and AgClO4 promoted regio-selective acylation of indoles
Kamble, Narendra R.,Pawar, Hari R.,Kamble, Vinod T.
, p. 317 - 321 (2020/01/08)
In present study, an efficient and simple strategy towards chemo-selective and regio-selective acylation of indole using NbCl5 and AgClO4 catalyst are reported. This method utilizes the catalytic potentiality of NbCl5 and AgClO4 towards acylation of unprotected indoles in a synergistic manner. The combination of these catalytic system results into numerous advantages such as excellent yields of product, short reaction times and easier isolation of products.
Synthesis of 3-acylindoles: via copper-mediated oxidative decarbethoxylation of ethyl arylacetates
Jaiswal, Anjali,Sharma, Anup Kumar,Singh, Krishna Nand
supporting information, p. 1623 - 1628 (2020/03/06)
An efficient regioselective C-3 acylation of free indoles (N-H) has been accomplished via oxidative decarbethoxylation of easily available ethyl arylacetates using Cu(OAc)2 and KOtBu in DMSO.