Trityl Isocyanide as a Mechanistic Probe in Multicomponent Chemistry: Walking the Line between Ugi- and Strecker-type Reactions

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...

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Vydané v:	Chemistry : a European journal Ročník 22; číslo 23; s. 7837 - 7842
Hlavní autori:	Cioc, Răzvan C., Preschel, Hans D., van der Heijden, Gydo, Ruijter, Eelco, Orru, Romano V. A.
Médium:	Journal Article
Jazyk:	English
Vydavateľské údaje:	WEINHEIM Blackwell Publishing Ltd 01.06.2016 Wiley Wiley Subscription Services, Inc
Predmet:	Acylation Amination Amines Amino acids Amino Acids - chemical synthesis Amino Acids - chemistry Chemistry Chemistry, Multidisciplinary chemoselectivity Combinatorial Chemistry Techniques - methods Condensation Cyanides Cyanides - chemical synthesis Cyanides - chemistry Imidazoles - chemical synthesis Imidazoles - chemistry Indicators and Reagents isocyanides multicomponent reactions nitrilium ion Pathways Physical Sciences Pyridines - chemical synthesis Pyridines - chemistry reactive intermediates Reagents Science & Technology Transformations Triphenylmethyl Compounds - chemical synthesis Triphenylmethyl Compounds - chemistry Walking chemoselectivity multicomponent reactions ORGANIC-SYNTHESIS 4-COMPONENT REACTION reactive intermediates MOLECULAR DIVERSITY CONVERTIBLE ISOCYANIDE isocyanides HETEROCYCLES nitrilium ion 3-COMPONENT CONDENSATION HIGHLY STEREOSELECTIVE-SYNTHESIS EFFICIENT DERIVATIVES PYRAZINES
ISSN:	0947-6539, 1521-3765, 1521-3765
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Shrnutí:	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.
Bibliografia:	istex:771EC43F7C30B2AB24327BBD88917E653E188771 ArticleID:CHEM201600285 ark:/67375/WNG-X4S3WMFJ-V EFPIA companies European Union's Seventh Framework Programme - No. FP7/2007-2013 ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 14 content type line 23
ISSN:	0947-6539 1521-3765 1521-3765
DOI:	10.1002/chem.201600285