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Catalyst‐Free, Glycerol‐Assisted Facile Approach to Imidazole‐Fused Nitrogen‐Bridgehead Heterocycles
Author(s) -
Tufail Fatima,
Singh Swastika,
Saquib Mohammad,
Tiwari Jyoti,
Singh Jaya,
Singh Jagdamba
Publication year - 2017
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201700557
Subject(s) - imidazole , catalysis , regioselectivity , chemistry , combinatorial chemistry , organic chemistry , nitrogen , aryl , glycerol , reaction conditions , green chemistry , reaction mechanism , alkyl
Abstract A completely regioselective, environmentally benign strategy for the facile synthesis of biologically important imidazole‐fused nitrogen‐bridgehead heterocycles has been developed using glycerol/water 4:1 as a green promoting media. The methodology involves the simple coupling of 2‐halocarbonyl compounds with 2‐aminopyridines, 2‐aminopyrimidines, 2‐aminopyrazines to obtain a variety of 2‐aryl substituted imidazo‐pyridines, imidazo‐pyrimidines and imidazo‐pyrazines containing bridgehead nitrogen. This protocol eliminates the use of toxic catalysts and volatile organic solvents ‐ two key principles in the development of a green chemical process. Other significant highlights include mild reaction conditions, operational simplicity, short reaction times, easy workup and purification process, high yields and potential for scale‐up.