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Trityl Isocyanide as a Mechanistic Probe in Multicomponent Chemistry: Walking the Line between Ugi- and Strecker-type Reactions.
- Source :
-
Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2016 Jun 01; Vol. 22 (23), pp. 7837-42. Date of Electronic Publication: 2016 Apr 26. - Publication Year :
- 2016
-
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.<br /> (© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.)
- Subjects :
- Acylation
Amination
Amino Acids chemistry
Combinatorial Chemistry Techniques methods
Cyanides chemical synthesis
Imidazoles chemistry
Indicators and Reagents
Pyridines chemistry
Trityl Compounds chemical synthesis
Amino Acids chemical synthesis
Cyanides chemistry
Imidazoles chemical synthesis
Pyridines chemical synthesis
Trityl Compounds chemistry
Subjects
Details
- Language :
- English
- ISSN :
- 1521-3765
- Volume :
- 22
- Issue :
- 23
- Database :
- MEDLINE
- Journal :
- Chemistry (Weinheim an der Bergstrasse, Germany)
- Publication Type :
- Academic Journal
- Accession number :
- 27112103
- Full Text :
- https://doi.org/10.1002/chem.201600285