Experimental and theoretical characterization of a novel bis‐pyrazoylmethane ligand

Ortíz, Pedro; Ortiz, Mayreli; Suardíaz, Reynier; Fragoso, Alex

doi:10.1002/mrc.4242

Cited by 2 publications

(2 citation statements)

References 32 publications

(9 reference statements)

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“…The structure of the product was established by 1D ( 1 H, 4 J HN coupling constants of the N atoms with their surrounding hydrogen atoms. [19] The observation of a cross peak between the ortho H atoms of the phenyl group and the imine-type N atom (δ 15 N = 279 ppm), together with an additional cross peak between the ortho H atoms of the tolyl group with the amine-type N atom (δ 15 N = 195 ppm) ascertained the proposed structure 4 ab and discarded an alternative regioisomer as 5 ab, whose spectrum should only display cross peaks at the same N chemical shift for the two types of ortho H atoms (Figure 1).…”

Section: Resultsmentioning

confidence: 99%

N‐Tosylhydrazones as [N,N] Synthons in Heterocyclic Chemistry: Synthesis of 3,5‐Disubstituted N‐Alkenyl‐1H‐pyrazoles

Velázquez‐Stavínov,

Piedra,

Gutiérrez‐Collar

et al. 2024

Adv Synth Catal

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A new mode of reactivity of <i>N</i>‐sulfonylhydrazones towards alkynes is described: ketone‐derived N‐tosylhydrazones (NTHs) bearing α‐H atoms behave as <i>[NN]</i> synthons in their reactions with alkoxy alkynyl Fischer carbene complexes (FCCs) and only the two N atoms are incorporated into the newly formed pyrazole ring. The scope of the reaction, leading to 5‐methoxy‐N‐alkenyl pyrazoles, proved to be wide regarding both partners; thus, a variety of aryl and primary, secondary, and tertiary alkyl substituents are tolerated within the FCC, while aryl alkyl NTHs, symmetric and asymmetric dialkyl NTHs and NTHs derived of cyclic ketones can be also employed. In addition, the reaction can be performed at large scale and applied for late‐stage diversification of natural products. A reasonable reaction mechanism is also proposed, which is supported by deuteration experiments and DFT calculations.

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Section: Resultsmentioning

confidence: 99%

N‐Tosylhydrazones as [N,N] Synthons in Heterocyclic Chemistry: Synthesis of 3,5‐Disubstituted N‐Alkenyl‐1H‐pyrazoles

Velázquez‐Stavínov,

Piedra,

Gutiérrez‐Collar

et al. 2024

Adv Synth Catal

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“…Comparative papers include a 13 C NMR study of polyphenyl-, poly-N-azolyl-and poly-Nbenzazolylmethanes [32]; a review on substituent effects on the 15 N NMR parameters of azoles [263]; a theoretical multinuclear NMR study of pyrazolylborates that includes for comparative purposes the parent pyrazolylmethanes 2, 1 and 15 [264]; and an experimental and theoretical (GIAO/DFT) study of the pyrenyl derivative 213 [265].…”

Section: Nmr Spectroscopymentioning

confidence: 99%

The organic chemistry of poly(1H-pyrazol-1-yl)methanes

Alkorta

Claramunt

Dı́ez-Barra

et al. 2017

Coordination Chemistry Reviews

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Since their first synthesis by Hückel (1937) and the first systematic exploration by Trofimenko (1970), interest in poly(1H-pyrazol-1-yl)methanes (bis, tris and tetrakis) has increased dramatically. This review focuses on the synthesis and reactivity of these ligands and contains 541 different structures and 271 references. After a brief historical introduction, the synthesis, reactivity, and nature of the coordinated metals are described along with some properties of these compounds, particularly the complete set of X-ray molecular structures. All of the formulae are represented to show the extraordinary richness of poly(1H-pyrazol-1-yl)methanes and to promote the use of the already known poly(1H-pyrazol-1-yl)methanes in coordination chemistry and the design of new ligands with the reported procedures. Keywords Pyrazoles Pyrazolylmethanes bis(1H-pyrazol-1-yl)methanes tris(1H-pyrazol-1yl)methanes tetrakis(1H-pyrazol-1-yl)methanes Metal ligands X-ray structures

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Experimental and theoretical characterization of a novel bis‐pyrazoylmethane ligand

Cited by 2 publications

References 32 publications

N‐Tosylhydrazones as [N,N] Synthons in Heterocyclic Chemistry: Synthesis of 3,5‐Disubstituted N‐Alkenyl‐1H‐pyrazoles

N‐Tosylhydrazones as [N,N] Synthons in Heterocyclic Chemistry: Synthesis of 3,5‐Disubstituted N‐Alkenyl‐1H‐pyrazoles

The organic chemistry of poly(1H-pyrazol-1-yl)methanes

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