Acid-promoted multicomponent allylic amidation towards 7-acetamido tetrahydroindole derivatives. Issue 5 (31st January 2019)

• Record Type: Journal Article
• Authors: Pramanik, Sayan; Maity, Suvendu; Ghosh, Prasanta; Mukhopadhyay, Chhanda
• Is Part Of: Tetrahedron letters. Volume 60:Issue 5(2019)
• Page Start: 435
• Page End: 438
• Publication Date: 2019-01-31
• Subjects: CH activation -- Allylic amidation -- TFA used as an acid catalyst -- Acetamido tetrahydroindole ring synthesis -- Multicomponent reactions; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2018.12.068
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Allylic sp 3 CH amidation through direct conversion of CH bonds to CN bonds. sp 3 CH amidation without use of any metal catalyst. Interesting combination of acid catalysis and multicomponent strategy. Biologically active acetamido tetrahydroindole moieties has been achieved. Abstract: An acid-promoted multicomponent reaction for the direct C(sp 3 )N bond formation was achieved through intermolecular allylic amidation in a one-pot operation to synthesize 7-acetamido tetrahydroindole derivatives from simple and readily available arylglyoxal monohydrates, acetonitriles, and enamines of 5, 5-dimethyl-1, 3-cyclohexadione (dimedone) has been developed. Here acetonitrile acts both as solvent and reagent. These tetahydroindole derivatives are formed through domino condensation of the enamines and arylglyoxals followed by annulation and allylic amidation.