Copper-based catalysts derived from salen-type ligands: synthesis of 5-substituted-1H-tetrazoles via [3+2] cycloaddition and propargylamines via A3-coupling reactions

Maji

et al. 2021

Applied Organom Chemis

Self Cite

Bis(imino)pyridine (NNN)‐type ligand [(PyPhime‐Cina) = 2,6‐bis((E)‐1‐phenyl‐2‐((E)‐3‐phenylallylidene)hydrazinyl)pyridine] was synthesized, and a new family of metal complexes [Mn(PyPhime‐Cina)Cl2] (1), [Fe(PyPhime‐Cina)Cl2] (2), [Co(PyPhime‐Cina)Cl2] (3), [Ni(PyPhime‐Cina)Cl2] (4), and [Cu(PyPhime‐Cina)Cl2] (5), derived from the ligand, have been synthesized and characterized. Molecular structures of the ligand and complexes 1‐5 were determined using X‐ray crystallography. Electronic properties and frontier molecular orbitals of the complexes were investigated by DFT and TD‐DFT calculations. DNA interaction studies were evaluated by UV‐visible absorption, fluorescence and circular dichroism spectral studies which indicated noncovalent binding of complexes with CT‐DNA. Hirshfeld surface analysis of all the complexes was studied to know the weak interaction present in the molecules.

Section: Resultssupporting

confidence: 89%

Section: Resultsmentioning

confidence: 99%

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A new family of complexes derived from bis(imino)pyridine‐type ligands: Crystal structures and bio‐molecular interaction studies

Maji

et al. 2021

Applied Organom Chemis

Self Cite

“…Synthesis of tetrazole using copper complexes. [127] Scheme 59. Synthesis of 5-1H-phenyl tetrazole in the presence of MCMBSA.…”

Section: Other Methods Of Tetrazole Synthesismentioning

confidence: 99%

Advances in Tetrazole Synthesis – An Overview

2022

Most of the active pharmaceutical ingredients (API) contain the tetrazole ring, thus making them of vast significance in new drug design descriptors. With this importance in view, enormous studies are being carried out on the synthesis of tetrazole derivatives. The methods of its synthesis are [3+2] cycloaddition, multicomponent reactions, microwave‐assisted synthesis using heterogeneous and homogeneous catalysts. Hence, it is necessary to highlight the green catalysis that would be more environmentally benign and economically viable. In this review, we discuss the tetrazole synthesis processes carried out in the presence of heterogeneous and homogeneous catalysts. These catalytic materials gave higher product yield in a shorter reaction time and were reusable.

“…In the same year, Singh reported a family of Cu(II) complexes that efficiently catalysed the A 3 coupling reaction at elevated temperatures, in toluene solvent, with very low catalyst loading and an extended scope [124]. Among this family of complexes, compound [Cu(II)(HL)(ClO 4 )] (11), shown in Figure 4, achieved the highest yields, leading the authors to suggest a possible mechanism that involved a Cu(I)-acetylide intermediate.…”

Section: Scheme 57 (Left)mentioning

confidence: 99%

Metal-Catalysed A3 Coupling Methodologies: Classification and Visualisation

2022

The multicomponent reaction of aldehydes, amines, and alkynes, known as A3 coupling, yields propargylamines, a valuable organic scaffold, and has received significant interest and attention in the last years. In order to fully realise the potential of the metal-based catalytic protocols that facilitate this transformation, we summarise substrates, in situ and well-characterised synthetic methods that provide this scaffold and attempt a monumental classification considering several variables (Metal, Coordinating atom(s), Ligand type and name, in-situ or well-characterised, co-catalyst, catalyst and ligand Loading (mol%), solvent, volume, atmosphere, temperature, microwave, time, yield, selectivity (e.e. d.r.), substrate name, functionality, loading (amines, aldehydes, alkynes), and use of molecular sieves). This pioneering work creates a valuable database that contains 2376 entries and allows us to produce graphs and better visualise their impact on the reaction.