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Tetrazole‐Substituted Five, Six, and Seven‐Membered Cyclic Amines Bearing Perfluoroalkyl Groups – Efficient Synthesis by Azido‐Ugi Reaction
Author(s) -
Shmatova Olga I.,
Nenajdenko Valentine G.
Publication year - 2013
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.201300861
Subject(s) - tetrazole , chemistry , isocyanide , ring (chemistry) , ugi reaction , cyclic amines , combinatorial chemistry , catalysis , medicinal chemistry , organic chemistry
Abstract The application of perfluoroalkylated cyclic imines in azido‐Ugi reactions was studied. It was shown that the reaction allows access to five‐, six‐ and seven‐membered perfluoroalkylated cyclic amines connected to a tetrazole ring. The scope and limitations of this approach are discussed. When benzyl isocyanide was used in the azido‐Ugi reaction, it was shown that the tetrazole products could easily be debenzylated by catalytic hydrogenation to form 1 H ‐tetrazoles in excellent yields.