Direct C-2 arylation of alkyl 4-thiazolecarboxylates: new insights in synthesis of heterocyclic core of thiopeptide antibiotics.
The Pd(0)-catalyzed regioselective C-2 (hetero)arylation of tert-butyl 4-thiazolecarboxylate with a broad (hetero)aryl halide is reported, including the direct coupling of pyridinyl halides. The process has allowed the preparation of valuable 2-pyridynyl-4-thiazolecarboxylates which are components of the complex heterocyclic core of thiopeptides antibiotics. As a first application, a synthesis of a tert-butyl sulfomycinamate thio-analogue from tert-butyl 4-thiazolecarboxylate is here described through a three-step direct pyridinylation, halogenation, and Stille cross-coupling sequence.
Institut de Chimie Organique Fine (IRCOF) associé au CNRS (UMR 6014), INSA et Université de Rouen, BP08 76131 Mont Saint Aignan, France.
Thibaut
T
Martin
Cécile
C
Verrier
Christophe
C
Hoarau
Francis
F
Marsais
D000478:Alkylation; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D002244:Carbon / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D013844:Thiazoles / Q000737:chemistry*
D000900:Anti-Bacterial Agents; D002264:Carboxylic Acids; D006571:Heterocyclic Compounds; D010455:Peptides; D013844:Thiazoles; D002244:Carbon