Cleavable β-Cyanoethyl Isocyanide in the Ugi Tetrazole Reaction.
β-Cyanoethyl isocyanide is introduced as a cleavable isocyanide in the Ugi tetrazole reaction. Eleven examples are described that exhibit a broad scope and are obtained in good overall yields. The obtained 1H-tetrazole scaffold is an important bioisostere for carboxylic acids, and the method described here is a valuable alternative route to known procedures.
University of Groningen , Department of Drug Design, A. Deusinglaan 1, 9713 AV Groningen, The Netherlands.
Edwin
E
Kroon
Jagiellonian University , Department of Crystal Chemistry and Crystal Physics, Ingardena 3, 30-060 Krakow, Poland.
Katarzyna
K
Kurpiewska
Jagiellonian University , Department of Crystal Chemistry and Crystal Physics, Ingardena 3, 30-060 Krakow, Poland.
Justyna
J
Kalinowska-Tłuścik
University of Groningen , Department of Drug Design, A. Deusinglaan 1, 9713 AV Groningen, The Netherlands.
Alexander
A
Dömling
D060326:Chemistry Techniques, Synthetic / Q000379:methods; D002626:Chemistry, Pharmaceutical; D003486:Cyanides / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D013777:Tetrazoles / Q000138:chemical synthesis / Q000737:chemistry*
D003486:Cyanides; D013777:Tetrazoles