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- Title
Trityl Isocyanide as a Mechanistic Probe in Multicomponent Chemistry: Walking the Line between Ugi- and Strecker-type Reactions.
- Authors
Cioc, ăzvan C.; Preschel, Hans D.; van der Heijden, Gydo; Ruijter, Eelco; Orru, Romano V. A.
- Abstract
Herein, we describe the versatile application of triphenylmethyl (trityl) isocyanide in multicomponent chemistry. This reagent can be employed as a cyanide source in the Strecker reaction and as convertible isocyanide in the preparation of N-acyl amino acids by Ugi 4CR/detritylation and free imidazo[1,2-a]pyridin-3-amines by a Groebke-Blackburn-Bienaymé 3CR condensation/deprotection protocol. The mechanisms of these three classical MCRs intersect at the common N-trityl nitrilium ion intermediate, whose predictable reactivity can be exploited towards chemoselective transformations.
- Subjects
ISOCYANIDES; CHEMICAL reactions; CHEMICAL reagents; CHEMICAL sample preparation; NITRILIUM ions; CHEMOSELECTIVITY
- Publication
Chemistry - A European Journal, 2016, Vol 22, Issue 23, p7837
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201600285