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Selective Synthesis of Tetrasubstituted 4‐(Tetrazol‐5‐yl)‐1 H ‐imidazoles from 2‐(Tetrazol‐5‐yl)‐2 H ‐azirines
Author(s) -
Cardoso Ana Lúcia,
Lemos Américo,
Pinho e Melo Teresa M. V. D.
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402559
Subject(s) - chemistry , reactivity (psychology) , imidazole , molecule , tetrazole , stereochemistry , combinatorial chemistry , medicinal chemistry , organic chemistry , medicine , alternative medicine , pathology
The reactivity of 2‐(tetrazol‐5‐yl)‐2 H ‐azirines towards imines in the presence of Lewis acids was explored, which opened a way to new tetrazol‐5‐yl‐1 H ‐imidazole derivatives. The Zn(OTf) 2 ‐catalyzed reaction allowed the selective synthesis of 4‐(tetrazol‐5‐yl)‐1 H ‐imidazole derivatives. The presence of phenyl or heteroaromatic substituents in both reactants permitted the synthesis of a wide range of multisubstituted imidazoles, which are molecules with potential relevance in medicinal chemistry.