N^N^O hydrazone capped pincer type palladium complex catalysed construction of quinazolinones from alcohols

Anandaraj, Pennamuthiriyan; Ramesh, Rengan; Kamatchi, Thangavel Sathiya

doi:10.1016/j.inoche.2021.109190

Cited by 6 publications

(1 citation statement)

References 45 publications

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“…Anandaraj et al . reported a Pd‐pincer type hydrazone complex for quinazolinone synthesis under aerobic condition in 2021 [47] . Similarly, we are interested in creating air‐stable, less toxic Ru hydrazone complexes with improved catalytic activity for synthesizing benzimidazole and quinazolinone derivatives.…”

Section: Introductionmentioning

confidence: 99%

Solvent‐Free Synthesis of Substituted Benzimidazoles and Quinazolinones via Acceptorless Dehydrogenative Coupling Using Ferrocene‐Hydrazone‐Based Ru(II)‐p–cymene Catalysts

Yadav

Tamizh

et al. 2023

Asian J Org Chem

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A series of ferrocene‐hydrazone based Ru(II)‐p‐cymene complexes were investigated for their catalytic activity towards acceptorless dehydrogenative coupling (ADC) reactions. Ru(II)‐p‐cymene isonicotinic Fc‐hyrazone complex performed better in the solvent‐free synthesis of 1,2‐disubstituted benzimidazoles (up to 88%) and quinazolinones (up to 95%). The catalysis was extended to a wide range of benzylic alcohols. The synthesis of 1,2‐disubstituted benzimidazoles was accomplished with electron‐donating/‐withdrawing o‐phenylenediamines as well. A catalytic structure‐activity relationship was established by varying the steric and electronic parameters on the substrates. All the catalytic experiments exhibited good to moderate yields, with hydrogen and water as the only by‐products. The prepared complexes were well characterized using analytical and spectroscopic techniques. The molecular structures of the ligands and complex were resolved using single crystal X‐ray crystallographic studies.

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Section: Introductionmentioning

confidence: 99%

Solvent‐Free Synthesis of Substituted Benzimidazoles and Quinazolinones via Acceptorless Dehydrogenative Coupling Using Ferrocene‐Hydrazone‐Based Ru(II)‐p–cymene Catalysts

Yadav

Tamizh

et al. 2023

Asian J Org Chem

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Concise access to perimidines by palladium (II) complexes via acceptorless dehydrogenative coupling of alcohols

Selvan

Ramesh

Małecki

2022

Applied Organom Chemis

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A facile protocol for the one-pot synthesis of 2,3-dihydro-1H-perimidines via dehydrogenative coupling of easily exploitable benzyl alcohols supported by new Pd(II) complexes has been reported. To accomplish the construction of perimidines, a new set of palladium(II) complexes [Pd(L)Cl (PPh 3 )] (1-3) encompassing biphenyl benzhydrazone ligands (L=L 1 -L 3 ) has been reported as catalysts. Structural characterization by elemental analysis, FT-IR, NMR( 1 H and 13 C), and mass spectral analyses confirmed the composition of synthesized complexes. The molecular structures complex 1 and complex 2 were unequivocally resolved using single-crystal X-ray diffraction. It reveals that the complex espoused distorted square-planar geometry around Pd(II) ion chelated by azomethine nitrogen and imidolate oxygen of biphenyl benzhydrazone ligands with labile chloride and a triphenylphosphine. Further, the selective synthesis of a broad range of functionalized perimidines has been accomplished via ADC of a variety of alcohols with 1,8-diamino naphthalene. The palladium complexes mediated catalytic synthesis offered good yields of perimidines up to 86% using only 0.5 mol% catalyst loading. A probable mechanism to the formation of perimidines was postulated from the results of control experimental investigations. The environmentally compassionate, greener ADC protocol progresses via the generation of aldehyde intermediate and releases only water and hydrogen gas.

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Design, synthesis, molecular docking, biological evaluation, DFT and ADME studies of novel bisquinazolinone derivatives

Ayoob,

Hawaiz

2023

Inorganic Chemistry Communications

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N^N^O hydrazone capped pincer type palladium complex catalysed construction of quinazolinones from alcohols

Cited by 6 publications

References 45 publications

Solvent‐Free Synthesis of Substituted Benzimidazoles and Quinazolinones via Acceptorless Dehydrogenative Coupling Using Ferrocene‐Hydrazone‐Based Ru(II)‐p–cymene Catalysts

Solvent‐Free Synthesis of Substituted Benzimidazoles and Quinazolinones via Acceptorless Dehydrogenative Coupling Using Ferrocene‐Hydrazone‐Based Ru(II)‐p–cymene Catalysts

Concise access to perimidines by palladium (II) complexes via acceptorless dehydrogenative coupling of alcohols

Design, synthesis, molecular docking, biological evaluation, DFT and ADME studies of novel bisquinazolinone derivatives

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