Real Multicomponent Reactions: Synthesis of Highly Substituted 2-Aminothiazoles

Frank Richter, Jennifer Seifert, Marcus Korb, Heinrich Lang, Klaus Banert

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

Allenyl isothiocyanates, which can be easily generated by flash vacuum pyrolysis, are known to readily form 1,3-thiazoles with various nucleophiles. This is also true for heterocyclic aromatic amines and sterically hindered amines that are in other aspects used as non-nucleophilic bases. The chemistry of these synthetically useful cumulenes is now expanded to the field of multicomponent reactions with the mentioned amines and selected electrophiles. In an efficient, catalyst-free three-component reaction (3-CR) sequence, highly substituted heterocyclic compounds are formed containing the 2-amino-1,3-thiazole skeleton. The reaction conditions and mechanisms leading to these potentially bioactive molecules were investigated and optimized for the synthesis of a small compound library.

Original languageEnglish
Pages (from-to)4673-4682
Number of pages10
JournalEuropean Journal of Organic Chemistry
Issue number34
DOIs
Publication statusPublished - 16 Sep 2018
Externally publishedYes

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