1092390-78-7Relevant articles and documents
FeCl3·6H2O as a Mild Catalyst for Nucleophilic Substitution of Symmetrical Bis(indoyl)methanes
Chantana, Chayamon,Jaratjaroonphong, Jaray
, p. 2312 - 2327 (2021/02/09)
In this paper, unsymmetrical bis(indolyl)methane (BIM) and 3-alkylindole derivatives are smoothly synthesized from symmetrical BIMs with a variety of nucleophiles including heteroaromatic/aromatic compounds, allylsilane and alkynylsilane. FeCl3·6H2O is found to be a mild and highly effective catalyst for this nucleophilic substitution reaction in which N-methyl-2-phenylindole behaves as a good leaving group in the Csp3-Csp2 bond cleavage reaction. The operational ease, nonexpensive and environmentally friendly catalyst, mild reaction conditions, broad functional group tolerance, and scalability of this reaction strategy are advantages of the present procedure.
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.
Br?nsted-Acid-Mediated Divergent Reactions of Betti Bases with Indoles: An Approach to Chromeno[2,3-b]indoles through Intramolecular Dehydrogenative C2-Alkoxylation of Indole
Deb, Mohit L.,Pegu, Choitanya Dev,Deka, Bhaskar,Dutta, Prantu,Kotmale, Amol S.,Baruah, Pranjal K.
, p. 3441 - 3448 (2016/07/23)
Divergent reactions of various 1-(aminoalkyl)naphthols and 2-(aminoalkyl)phenols (commonly known as Betti bases) with indoles under Br?nsted acid catalysis is reported. With the reaction strategies, one can efficiently synthesize important indole derivatives such as 3-(α,α-diarylmethyl)indoles and chromeno[2,3-b]indoles. Furthermore, we disclose here a new C–C bond-cleavage reaction, in which naphthol and phenol behave as leaving groups to produce diarylmethanes. Inexpensive reagents such as p-toluenesulfonic acid monohydrate and molecular iodine are used to catalyze the reactions. No metal catalyst is required. The starting material of the reactions, Betti bases, are easily prepared from a three-component reaction of naphthol/phenol, aldehydes, and secondary amines. The mechanisms for the reactions are established through some control experiments. Quinone methide is the key intermediate for all the reactions reported herein.
