γ‐Al 2 O 3  /triflic acid as cooperative catalysts for the tandem Michael addition/carbocyclization: An easy access to 2‐substituted pyrrolo[2,1‐ a ]isoquinolines and 3‐substituted pyrrolidine‐2,5‐diones | Zendy

Rao Ramana Sreenivasa | Zendy; Sahani Anita | Zendy; Ali Sheikh Haider | Zendy; Pradhan Sumanta | Zendy; Ramanathan Chinnasamy Ramaraj | Zendy

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γ‐Al 2 O 3 /triflic acid as cooperative catalysts for the tandem Michael addition/carbocyclization: An easy access to 2‐substituted pyrrolo[2,1‐ a ]isoquinolines and 3‐substituted pyrrolidine‐2,5‐diones

Author(s) -

Rao Ramana Sreenivasa,

Sahani Anita,

Ali Sheikh Haider,

Pradhan Sumanta,

Ramanathan Chinnasamy Ramaraj

Publication year - 2021

Publication title -

journal of heterocyclic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.321

H-Index - 59

eISSN - 1943-5193

pISSN - 0022-152X

DOI - 10.1002/jhet.4266

Subject(s) - chemistry , triflic acid , maleimide , nucleophile , tandem , catalysis , aryl , michael reaction , thio , x ray photoelectron spectroscopy , medicinal chemistry , organic chemistry , polymer chemistry , combinatorial chemistry , chemical engineering , materials science , composite material , alkyl , engineering

A tandem Michael addition/carbocyclization of 3,4‐dimethoxyphenethyl maleimide with carbon and sulfur nucleophiles is accomplished via a relay catalysis using γ‐Al 2 O 3 /TfOH binary system. The X‐ray Photoelectron Spectroscopy (XPS) analysis of binary system indicates the presence of AlF 3 , AlO(OH) species . This approach provides an easy access to 2‐aryl or 2‐thio aryl pyrrolo[2,1‐ a ]isoquinolines in good yields in a tandem fashion. With suitable ratio of γ‐Al 2 O 3 /TfOH binary system, the Michael addition of N/C/S nucleophiles to N ‐benzyl maleimide is also achieved. A key to the success of these reactions would be the generation of AlF 3 , AlO(OH) species from γ‐Al 2 O 3 and TfOH, which might have delineated the disadvantageous background reactions usually displayed by a strong Brønsted acid such as TfOH.

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