Synthesis of ferrocene annulated trifluoromethylated heterocycles with crispine and lamellarin skeletons

Korotaev, Vladislav Yu.; Kutyashev, Igor B.; Barkov, Alexey Yu.; Rozhkova, Yuliya S.; Plekhanova, I. V.; Shklyaev, Yurii V.; Sosnovskikh, Vyacheslav Ya.

doi:10.1016/j.tetlet.2019.07.007

Cited by 9 publications

(2 citation statements)

References 51 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In a subsequent study, 1-alkyl-3,4dihydroferroceno [c]pyridines were reacted with 1-nitro-1-(2,2,2trifluroethylidene)alkanes or 3-nitro-2-(trifluoromethyl)-2H-chromenes in 2-propanol at reflux to give ferrocene derivatives featuring a trifluromethyindolizine substructure. [54] In 2021, López and co-workers developed the regio-and stereoselective synthesis of tetrahydropyridine-fused ferrocene derivatives through a trifluoromethanesulfonic acid-catalyzed three-component reaction of racemic 2-aryl-N-sulfonyl aziridines, ferrocene, and formaldehyde (Scheme 21). [55] This multicomponent reaction proceeds through initial regioselective ring opening of the aziridine to furnish the corresponding βaminoethyl ferrocene derivatives (isolable in the absence of formaldehyde).…”

Section: Synthesis Of Dihydro-and Tetrahydro-pyridine-fused Ferrocenesmentioning

confidence: 99%

Synthesis and Applications of Ferrocene‐Fused Nitrogen Heterocycles

2021

View full text Add to dashboard Cite

The marriage of heterocyclic compounds with ferrocene has proven to be an extremely fruitful field of research. In fact, in the last years, several ferrocene-embedded heterocyclic compounds have been reported. In some cases, the synergistic combination of the properties of the heterocyclic and metal-lacyclic motifs provides to the fused systems interesting applications. This Review summarizes the major advances in the synthesis of ferrocene-fused nitrogen heterocyclic compounds and their applications, particularly in asymmetric catalysis.

show abstract

Section: Synthesis Of Dihydro-and Tetrahydro-pyridine-fused Ferrocenesmentioning

confidence: 99%

Synthesis and Applications of Ferrocene‐Fused Nitrogen Heterocycles

2021

View full text Add to dashboard Cite

show abstract

“…As a continuation of our program expanding the scope of ferrocene-containing heterocycles with potential biological relevance, we envisaged a preliminary study on the synthetic accessibility and structural characteristics of the first members of ferroceno[3,4]pyrrolo[2,1-b]thiazol-5(8bH)-ones. These organometallics, comprising the elements of planar- and central chirality, represent a novel class of ferrocene-fused heterocycles with well-defined stereostructures [ 12 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 ]. The diverse molecular architectures of known ferroceno-heterocycles have been assembled by a variety of synthetic methodologies including conventional organic heterocyclisations [ 12 , 17 , 18 , 19 ] and protocols based on transition metal-catalysed CH-activation [ 20 , 21 ], alkyne-mediated annulations [ 22 , 23 ], cross-coupling reactions [ 24 ], metal-free radical cyclisation [ 25 ] as well as iron-incorporation in the late-stage construction of the ferrocene moiety [ 26 ].…”

Section: Introductionmentioning

confidence: 99%

2,3-Dihydroferroceno[3,4]pyrrolo[2,1-b]thiazol-5(8b)-ones: Synthesis, Structure and DFT Study on the Mechanism of Chemo- and Diastereoslective Annulations of (Sp)-2-Formylferrocenecarbonyl Fluoride and (Sp)-2-Formylferrocenecarboxylic Acid

Kovács

Csámpai

2021

Molecules

View full text Add to dashboard Cite

By means of the annulation of easy-to-handle yet sufficiently reactive (Sp)-2-formylferrocenecar- bonyl fluoride with the hydrochlorides of cysteamine and the methyl esters of enentiomer cysteines conducted in dichloromethane at room temperature in the presence of pyridine, the first members of 2,3-dihydroferroceno[3,4]pyrrolo[2,1-b]thiazol-5(8bH)-ones with the elements of planar- and central chirality were prepared as single enantiomers. An atom economic procedure was also elaborated for the synthesis of these organometallic heterocycles directly exploring (Sp)-2-formylferrocenecarboxylic acid in situ activated by CDI and TFA, sequentially added to the reaction mixture. The relative and consequently, the absolute, configuration of the isolated diastereomers was determined by NMR measurements supported by DFT structural optimization. On the basis of the results of synthetic control experiments and a series of further DFT modelling studies, including energetic and MO analysis of the iminium intermediates, we propose a mechanism for the thiazolidine-forming annulations that proceed via primary N-acylation followed by proton-mediated cyclocondensation and subsequent diastereoselective sulfhydryl-attack on the resulting iminium center.

show abstract

Novel π‐Extended Quinazoline‐Ferrocene Conjugates: Synthesis, Structure, and Redox Behavior

2020

View full text Add to dashboard Cite

Novel ferrocene conjugates of tricyclic quinazoline derivatives are prepared by condensation of active C‐6 methylene groups of mackinazolinones with ferrocenecarbaldehyde. Following this route the conjugated parent alkaloid as well as derivatives with nitro, amino, and alkanoylamino groups at C‐2 were attached at the ferrocene moiety, thereby significantly extending the delocalized π system. In addition, the parent compound was subjected to the reaction with ferrocene‐1,1'‐dicarbaldehyde, giving rise to the symmetrical and unsymmetrical double condensation products – 1,1'‐disubstituted ferrocene derivatives, which bear two alkaloid substituents. Some of the compounds obtained were subjected to X‐ray crystallographic analyses. The influence of the substituents at C‐2 through the extended conjugated π system on the iron atom is reflected by results of cyclovoltammetric measurements.

show abstract

Synthesis of ferrocene annulated trifluoromethylated heterocycles with crispine and lamellarin skeletons

Cited by 9 publications

References 51 publications

Synthesis and Applications of Ferrocene‐Fused Nitrogen Heterocycles

Synthesis and Applications of Ferrocene‐Fused Nitrogen Heterocycles

2,3-Dihydroferroceno[3,4]pyrrolo[2,1-b]thiazol-5(8b)-ones: Synthesis, Structure and DFT Study on the Mechanism of Chemo- and Diastereoslective Annulations of (Sp)-2-Formylferrocenecarbonyl Fluoride and (Sp)-2-Formylferrocenecarboxylic Acid

Novel π‐Extended Quinazoline‐Ferrocene Conjugates: Synthesis, Structure, and Redox Behavior

Contact Info

Product

Resources

About