51626-58-5Relevant articles and documents
Accelerating Amine-Catalyzed Asymmetric Reactions by Intermolecular Cooperative Thiourea/Oxime Hydrogen-Bond Catalysis
Afewerki, Samson,Córdova, Armando,Ibrahem, Ismail,Ma, Guangning,Zhang, Kaiheng
, p. 3043 - 3049 (2021)
The ability of intermolecular cooperative thiourea/oxime hydrogen-bond catalysis for improving and accelerating asymmetric aminocatalysis is presented. The two readily available hydrogen-bond-donating catalysts operates in synergy with a chiral amine catalyst to accomplish highly stereoselective transformations. The synergistic catalyst systems simultaneously activate both electrophiles and nucleophiles, and make the transformations more chemo- and stereoselective. This was exemplified by performing co-catalytic enantioselective direct intermolecular α-alkylation reactions of aldehydes, direct aldol reactions, and asymmetric conjugate reactions, which gave the corresponding products in high yields and enantiomeric ratios.
A novel base-promoted synthesis of β-indolylketones via a three-component condensation under ultrasonic irradiation
Shen, Zhi-Liang,Ji, Shun-Jun,Wang, Shun-Yi,Zeng, Xiao-Fei
, p. 10552 - 10558 (2005)
A convenient, efficient, and practical method for the synthesis of β-indolylketones via a condensation of indole, aromatic aldehydes, and deoxybenzoin under ultrasonic irradiation was described. It provided a novel base-promoted approach for the one-pot synthesis of β-indolylketones.
Base-Promoted Three-Component One-Pot Approach to 3-(α,α-Diarylmethyl)indoles via Arylation of 3-Indolylalcohols
Deb, Mohit L.,Borpatra, Paran J.,Saikia, Prakash J.,Baruah, Pranjal K.
, p. 1401 - 1409 (2017)
A base-promoted 3-component one-pot approach to 3-(α,α-diarylmethyl)indoles via arylation of in situ generated 3-indolylalcohols in ethanol-water solvent system is reported. Use of acid catalysts or neutral organocatalysts does not offer the desired product, but furnish bis(indolyl)methanes instead. Electron-rich aromatics such as naphthols and phenols are preferably employed for arylation. The atom economy, use of green solvent, and the multicomponent strategy are the notable features of the reaction.
Lewis Acid Catalyzed Three-Component [3+2] Cycloaddition Reaction Using Pentafulvene as 2π Component: An Easy Way to Construct Pentaleno(1,2-b)indoles
Santhini,Sarath Chand,John, Jubi,Varma, R. Luxmi,Jaroschik, Florian,Radhakrishnan
, p. 951 - 956 (2017)
A facile route toward the synthesis of pentaleno(1,2-b)indoles via multicomponent reaction of indole, aldehyde, and pentafulvene is realized. The reaction proceeds through Lewis acid catalyzed [3+2] cycloaddition of in situ generated indolylmethanol and pentafulvene. This methodology provides an easy access to biologically relevant indole derivatives.
Lewis Acid-Catalyzed [3+3] Annulation of Donor-Acceptor Cyclopropanes and Indonyl Alcohols: One Step Synthesis of Substituted Carbazoles with Promising Photophysical Properties
Varshnaya, Rohit Kumar,Banerjee, Prabal
, p. 1614 - 1623 (2019/02/07)
A highly efficient protocol to access carbazole from donor-acceptor cyclopropane and indonyl alcohol via [3+3] annulation in the presence of a Lewis acid has been demonstrated. This method facilitates the post functionalization of the substituted carbazol
Highly Diastereo- and Enantioselective Synthesis of Cyclohepta[b]indoles by Chiral-Phosphoric-Acid-Catalyzed (4+3) Cycloaddition
Gelis, Coralie,Levitre, Guillaume,Merad, Jérémy,Retailleau, Pascal,Neuville, Luc,Masson, Géraldine
supporting information, p. 12121 - 12125 (2018/09/11)
A highly enantio- and diastereoselective formal (4+3) cycloaddition of 1,3-diene-1-carbamates with 3-indolylmethanols in the presence of a chiral phosphoric acid catalyst is reported. The approach described herein provides efficient access to 6-aminotetrahydrocyclohepta[b]indoles in good yields with mostly complete diastereoselectivity and excellent levels of enantioselectivity (>98:2 dr and up to 98 % ee). Mild reaction conditions, facile scale-up, and versatile derivatization highlight the practicality of this methodology. A mechanistic study suggests that cycloaddition occurs in a stepwise fashion, after the formation of an ion pair between the chiral catalytic phosphate and the intermediate carbocation.
One-pot sequential multi-component reaction: Synthesis of 3-substituted indoles
Borpatra, Paran J.,Deka, Bhaskar,Rajbongshi, Basanta K.,Deb, Mohit L.,Baruah, Pranjal K.
supporting information, p. 2074 - 2082 (2018/07/15)
Here, we have developed a 3-component one-pot sequential approach to 3-substituted indoles. The main advantages of this process are step economy, reduced waste, and operational simplicity. The method involves in situ generation of 3-indolylalcohols from t
Palladium-catalyzed oxidative arylacetoxylation of alkenes: Synthesis of indole and indoline derivatives
Karnakanti, Shuklachary,Zang, Zhong-Lin,Zhao, Sheng,Shao, Pan-Lin,Hu, Ping,He, Yun
supporting information, p. 11205 - 11208 (2017/10/17)
A method for the oxidative arylacetoxylation of alkenes has been developed to synthesize indole and indoline derivatives from readily accessible substrates. The cinnamyl tethered anilines with picolinamide as a directing group provided 3-substituted indoles via intramolecular oxidative arylacetoxylation, and the 2-methyl substituted cinnamyl anilines furnished indoline derivatives with 3-position quaternary stereocenters in good to excellent yields via sequential intramolecular oxidative arylacetoxylation, hydrolysis and oxidation steps.
Base-promoted three-component cascade approach to unsymmetrical bis(indolyl)methanes
Deb, Mohit L.,Deka, Bhaskar,Saikia, Prakash J.,Baruah, Pranjal K.
supporting information, p. 1999 - 2003 (2017/04/27)
Here we report a base-catalyzed reaction of two different indoles with aldehydes under heating to produce unsymmetrical bis(indolyl)methanes (BIMs), in which one of the indole ring must be N-substituted. Mixture of EtOH-H2O is used as solvent. The reaction did not give symmetrical BIMs of N-substituted indoles or N–H indoles. However, traces of latter were formed in few cases, especially when electron-rich aldehydes were used. Diversely substituted indoles and aldehydes were used for the reaction. The reaction proceeds via 3-indolylalcohol, which we confirmed through isolation. The method also gives good yield on multigram scale reaction.
Exploration of Aberrant Behaviour of Grignard Reagents with Indole-3-carboxaldehyde: Application to the Synthesis of Turbomycin B and Vibrindole A Derivatives
Bahuguna,Sharma,Sagara,Ravikumar
supporting information, p. 117 - 121 (2016/12/26)
An aberrant reaction of Grignard reagents with N-alkylated indole-3-carboxaldehyde has been observed. Contrary to the usual formation of an alcohol, it afforded an unusual bis(indolyl)methane product. A systematic study on this new mode of reactivity and its application to a synthesis of the potent antibiotic turbomycin B and vibrindole A derivatives is reported.
