Brønsted-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.

Divergent reactions of various 1-(aminoalkyl)naphthols and 2-(aminoalkyl)phenols (commonly known as Betti bases) with indoles under Brønsted 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.

CHEMICAL reactions; INDOLE; ALKOXYLATION; HETEROCYCLIC compounds; AMINES

European Journal of Organic Chemistry, 2016, Vol 2016, Issue 20, p3441

1434-193X

Academic Journal

10.1002/ejoc.201600546