Trityl Isocyanide as a Mechanistic Probe in Multicomponent Chemistry: Walking the Line between Ugi‐ and Strecker‐type Reactions |
| |
Authors: | Răzvan C. Cioc Hans D. Preschel Gydo van der Heijden Dr. Eelco Ruijter Prof. Dr. Romano V. A. Orru |
| |
Affiliation: | Department of Chemistry & Pharmaceutical Sciences and, Amsterdam Institute for Molecules Medicines and Systems (AIMMS), Vrije Universiteit Amsterdam, Amsterdam, The Netherlands |
| |
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. |
| |
Keywords: | chemoselectivity isocyanides multicomponent reactions nitrilium ion reactive intermediates |
|