674768-69-5Relevant articles and documents
Trityl Isocyanide as a Mechanistic Probe in Multicomponent Chemistry: Walking the Line between Ugi- and Strecker-type Reactions
Cioc, Rǎzvan C.,Preschel, Hans D.,Van Der Heijden, Gydo,Ruijter, Eelco,Orru, Romano V. A.
supporting information, p. 7837 - 7842 (2016/06/09)
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. Fate of the nitrilium ion: The application of trityl isocyanide as a mechanistic tool to dissect different reaction pathways in multicomponent chemistry is described. This reagent can be employed as a cyanide source in the Strecker reaction and as a convertible isocyanide in the preparation of N-acyl amino acids by Ugi 4CR/detritylation and free imidazo[1,2-a]pyridin-3-amines by Groebke-Blackburn-Bienaymé 3CR condensation/deprotection. Chemoselective transformations were achieved by the rational choice of reaction conditions.
