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Sequential One‐Pot Synthesis of Imidazoles and 2H ‐Imidazolones from β‐Ketoamines, Acylating Agents and Ammonium Acetate
Author(s) -
Jalani Hitesh B.,
Venkateswararao Eeda,
Manickam Manoj,
Jung SangHun
Publication year - 2016
Publication title -
bulletin of the korean chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.237
H-Index - 59
ISSN - 1229-5949
DOI - 10.1002/bkcs.11005
Subject(s) - ammonium acetate , chemistry , acylation , combinatorial chemistry , organic chemistry , reaction conditions , ammonia , catalysis , high performance liquid chromatography
An efficient, practical, straight forward, and transition metal‐free three‐component synthesis of diversely substituted imidazoles and 2H ‐imidazolones from β‐ketoamines, acylating agents, and ammonium acetate has been described herein. This approach involves [3+1+1] cyclization through consecutive formation of three C–N bonds as a sequence of initial amidation of β‐ketoamines with acylating agent, β‐iminoketoamide formation with ammonia, and acid catalyzed concomitant cyclodehydration to afford the imidazoles and 2H ‐imidazolones. This methodology has advantages such as single flask operation, readily available starting materials, mild conditions, broad functional groups tolerance, and simple work‐up procedure.