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TMSOTf‐Catalysed Synthesis of 2,4,5‐Trisubstituted Imidazoles from Vinyl Azides and Nitriles
Author(s) -
Harisha Mysore Bhyrappa,
Dhanalakshmi Pandi,
Suresh Rajendran,
Kumar Raju Ranjith,
Muthusubramanian Shanmugam,
Bhuvanesh Nattamai
Publication year - 2019
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201801543
Subject(s) - chemistry , tautomer , imidazole , structural isomer , organic chemistry , combinatorial chemistry , substrate (aquarium) , reaction conditions , catalysis , oceanography , geology
TMSOTf‐catalysed generation of 2,4,5‐trisubstituted imidazoles by a simple [3+2] addition reaction of azido chalcones and organic nitriles is described. This transformation generates two new C‐N bonds under mild reaction conditions. The substrate scope of the reaction is excellent with good number of vinyl azides and aromatic and aliphatic nitriles tolerating the reaction. It has been shown that the reaction can also be conducted under microwave condition successfully. These newly synthesized imidazoles are shown to exist as tautomeric mixture and the subsequent methylated as well as benzylated compounds have been obtained as a single regioisomer. The synthesised N‐methyl Imidazole derivative is a potential structural unit towards biologically active compounds.