Real Multicomponent Reactions: Synthesis of Highly Substituted 2-Aminothiazoles

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

Research output: Contribution to journalArticle

4 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

Cite this

Richter, Frank ; Seifert, Jennifer ; Korb, Marcus ; Lang, Heinrich ; Banert, Klaus. / Real Multicomponent Reactions : Synthesis of Highly Substituted 2-Aminothiazoles. In: European Journal of Organic Chemistry. 2018 ; No. 34. pp. 4673-4682.
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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.",
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Real Multicomponent Reactions : Synthesis of Highly Substituted 2-Aminothiazoles. / Richter, Frank; Seifert, Jennifer; Korb, Marcus; Lang, Heinrich; Banert, Klaus.

In: European Journal of Organic Chemistry, No. 34, 16.09.2018, p. 4673-4682.

Research output: Contribution to journalArticle

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