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Synthesis 2017; 49(12): 2700-2710
DOI: 10.1055/s-0036-1588966
DOI: 10.1055/s-0036-1588966
paper
Synthesis of Novel Five- and Six-Membered Ferrocene-Containing Heterocycles and Heteroaromatics via Cyclocondensation of 1-Ferrocenyl-3,3-bis(methylthio)prop-2-en-1-one with Various Bifunctional Nucleophiles
Further Information
Publication History
Received: 21 November 2016
Accepted after revision: 16 February 2017
Publication Date:
10 March 2017 (online)
Dedicated to the memory of Professor Jean F. Normant
Abstract
Synthesis and reactions of 1-ferrocenyl-3,3-bis(methylthio)prop-2-en-1-one as a versatile 1,3-bielectrophilic synthon leading to a range of novel ferrocene-containing five- and six-membered heterocycles and heteroaromatics has been reported. Thus its cyclocondensation with various bifunctional heteronucleophiles, such as hydrazine, phenylhydrazine, hydroxylamine, guanidine, and amidine, affords a range of ferrocene-substituted pyrazoles, oxazoles, and pyrimidines in highly regioselective manner. Synthesis of few ferrocenyl-substituted pyridines and thiophenes has also been described. Similarly cycloaromatization of this ferrocene-substituted α-oxoketene dithioacetal with anions generated from (het)arylacetonitriles provides a facile entry to ferrocene-substituted heteroaromatics in good yields. Synthesis of a few 2-ferrocenylvinyl-substituted heterocycles, such as pyrazoles, isoxazoles, and pyrimidines, via cyclocondensation of a novel 5-ferrocenyl-1,1-bis(methylthio)penta-1,4-dien-3-one with phenylhydrazine, hydroxylamine, and guanidine has also been reported.
Key words
α-oxoketene dithioacetal - ferrocene-containing heterocycles - cyclocondensation - cycloaromatization - phenylhydrazine - hydroxylamine - amidineSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588966.
- Supporting Information
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