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Selective Formation of 2‐Imidazolines and 2‐Substituted Oxazoles by Using a Three‐Component Reaction
Author(s) -
Elders Niels,
Ruijter Eelco,
de Kanter Frans J. J.,
Groen Marinus B.,
Orru Romano V. A.
Publication year - 2008
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200800271
Subject(s) - component (thermodynamics) , chemistry , catalysis , solvent , combinatorial chemistry , scope (computer science) , reaction conditions , scaffold , organic chemistry , computer science , database , physics , thermodynamics , programming language
Abstract Selective formation of 2 H ‐2‐imidazolines and 2‐substituted oxazoles by using a multicomponent reaction of amines, either aldehydes or ketones, and α‐acidic isocyano amides or esters is described. By selecting the appropriate solvent, Ag I or Cu I catalyst, or by employing a weak Brønsted acid, the product formation can be fully controlled and directed quantitatively to the desired heterocyclic scaffold. The described experimental procedures not only significantly increase the scope of compatible inputs for this complexity‐generating three‐component reaction, but also allow for considerable chemical diversity: At least four diversity points in two distinct scaffolds can be exploited in this way.