Trinuclear cis–[MoVIO2] complexes catalyzed efficient synthesis of 3,4-dihydropyrimidin-2(1H)-one based biomolecules via one-pot-three-components Biginelli reaction under solvent-free condition

Maurya, Mannar R.; Singh, Devesh Kumar; Tomar, Reshu; Gupta, Puneet

doi:10.1016/j.ica.2021.120750

Cited by 12 publications

(12 citation statements)

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“…The quality of MeOH is possibly responsible for such a coordination of water molecule, and is known in the literature. 19…”

Section: Resultsmentioning

confidence: 99%

“…Our interest in open-structured polynuclear dioxidomolybdenum( vi ) complexes with a weakly coordinated solvent molecule led us to design bis{ cis -[Mo VI O 2 ]} with binucleating ligands and C 3 symmetric tris{ cis -[Mo VI O 2 ]} complexes with tri-compartmental ligands, and explore their catalytic potentials. 19,24 In the present study, we report tri-nuclear cis -[Mo VI O 2 ] complexes with newly designed C 3 symmetric tri-compartmental ligands based on benzene-1,3,5-tricarbohydrazide and different derivatives of pyrazolone (Scheme 1).…”

Section: Introductionmentioning

confidence: 96%

“…12–15 Other catalytic reactions include sulfide oxidation, 16,17 oxidative bromination of organic substrates 18 and multicomponent one-pot reaction (MCR). 19…”

Section: Introductionmentioning

confidence: 99%

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Trinuclear dioxidomolybdenum(vi) complexes derived from benzene-1,3,5-tricarbohydrazide and study of the catalytic activity

et al. 2023

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“…The quality of MeOH is possibly responsible for such a coordination of water molecule, and is known in the literature. 19…”

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 96%

See 1 more Smart Citation

Trinuclear dioxidomolybdenum(vi) complexes derived from benzene-1,3,5-tricarbohydrazide and study of the catalytic activity

et al. 2023

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“…Thus, based on the observations from the interactions of complex 6 with H 2 O 2 , benzaldehyde, ethyl acetoacetate and ammonia, and in the light of the recently proposed mechanism from DFT study, [42,43] the following catalytic cycle (Scheme 6) may be proposed here. It is to be noted that DFT study recently carried out for mononuclear cis-[MoO 2 ] complex confirms the stabilization of intermediates 2 and 4.…”

Section: Putative Reaction Mechanismmentioning

confidence: 96%

“…It is to be noted that DFT study recently carried out for mononuclear cis-[MoO 2 ] complex confirms the stabilization of intermediates 2 and 4. [42,43]…”

Section: Putative Reaction Mechanismmentioning

confidence: 99%

Influence of Coordination Geometry on the Ring Opening of Benzoxazine: Oxidovanadium(V), Dioxidomolybdenum(VI) and Dioxidotungsten(VI) Complexes of Benzoxazine Based Ligands and their Bio Inspired Catalytic Applications

et al. 2022

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Mono benzoxazine appended N‐capped amino bis(disubstitutedphenol) ligands [II(a–c)] upon reaction with VVO(OEt)3 in a 1 : 1 molar ratio in EtOH/MeOH give [{VVO}en(3,5‐dtbb)3] (1), [{VVO}en(3‐tb,5‐mb)3] (2) and [{VVO}en(3,5‐dmb)3] (3). During the reaction, the benzoxazine ring opens with the loss of methylene group and the newly formed ligands, N,N‐bis(2‐hydroxy‐3,5‐disubstitutedbenzyl)‐N’‐2‐hydroxy‐3,5‐disubstituted benzyledene‐1,2‐diaminoethane [III(a–c)], behave as tribasic pentadentate in these complexes. Under similar conditions, when [MVIO2(acac)2] (M=Mo or W; Hacac=acetylacetone) reacts with II(a–c), these ligands retain their identity and form cis‐[MVIO2] complexes, [{MoVIO2}{en(3,5‐dtbb)2(6,8‐dtbbenzox)}] (4), [{MoVIO2}{en(3‐tb,5‐mb)2(6‐tb,8‐mbbenzox)}] (5) and [{MoVIO2}{en(3,5‐dmb)2(6,8‐dmbenzox)}] (6), [{WVIO2}{en(3,5‐dtbb)2(6,8‐dtbbenzox)}] (7), and [{WVIO2}{en(3‐tb,5‐mb)2(6‐tb,8‐mbbenzox)}] (8). However, the benzoxazine ring ruptures in case of ligand IIc under these conditions and form [{WVIO2}{en(3,5‐dmb)3}] (10), similar to complexes 1–3. Complex [{WVIO2}{en(3,5‐dmb)2(6,8‐dmbenzox)}] (9), having structure similar to 4–8, could only be obtained when the reaction was carried out in toluene. Not only 9, even complexes 4–8 can be isolated in toluene. Rupturing of both benzoxazine rings has also been experienced when ligands 1,2‐bis(6,8‐disubstitutedbenzo[e][1,3]oxazin‐3(4H)‐yl)ethane [I(a–c)] react with [MVIO2(acac)2] (M=Mo or W) in MeOH and give salan type complexes [(MVIO2)en(3,5‐dtbb)2] [M=Mo (11), M=W (14)], [(MVIO2)en(3‐tb,5‐mb)4] [M=Mo (12), M=W (15)] and [(MVIO2)en(3,5‐dmb)4] [M=Mo (13), M=W (16)]. Complexes 1–9 have been used as catalyst for the multicomponent Biginelli reaction for the synthesis of 3,4‐dihydropyrimidin‐2(1H)‐ones (DHPMs) and oxidative bromination of phenol derivatives.

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Catalytic Potential of Pyrazolone Based Dioxidomolybdenum(VI) Complexes for Multicomponent Biginelli Reactions, Epoxidation of Olefins and Oxidative Bromination of Phenol Derivatives

Maurya,

Singh,

Bisht

et al. 2023

Eur J Inorg Chem

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Three different types of dioxidomolybdenum(VI) complexes of 4‐acetyl‐3‐methyl‐1‐phenyl‐5‐pyrazolone (Hmp, I)), 3‐methyl‐1‐phenyl‐4‐propionyl‐5‐pyrazolone (Hpp, II), 4‐butyryl‐3‐methyl‐1‐phenyl‐5‐pyrazolone (Hbutp, III), and 4‐isobutyryl‐3‐methyl‐1‐phenyl‐5‐pyrazolone (isobutp, IV) have been isolated and characterized by various spectroscopic (FT‐IR, UV/Vis, 1H and13C NMR) techniques, thermal analysis and single crystal X‐ray analysis. These complexes adopt a distorted six‐coordinated octahedral geometry where ligands act as bidentate, coordinating through the two O atoms. These complexes have been used as catalysts to explore a single pot multicomponent (benzaldehyde or its derivatives, urea/thiourea and ethyl acetoacetate/phenyl acetoacatate) Biginelli reaction producing biologically active 3,4‐dihydropyrimidin‐2‐(1H)‐one and 3,4‐dihydropyrimidin‐2‐(1H)‐thione based biomolecules under solvent‐free conditions. Presence of H2O2 improves the yield of dihydropyrimidin‐2‐(1H)‐one but it acts as poisons for the later molecule. Epoxidation of internal and terminal alkenes mainly resulted in the formation of the corresponding epoxide selectively. The catalytic oxidative bromination of thymol, a reaction facilitated by vanadium dependent haloperoxidases, resulted in the formation of three product namely 2‐bromothymol, 4‐bromothymol and 2,4‐bromothymol. Other phenol derivatives have also been brominated effectively.

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Trinuclear cis–[MoVIO2] complexes catalyzed efficient synthesis of 3,4-dihydropyrimidin-2(1H)-one based biomolecules via one-pot-three-components Biginelli reaction under solvent-free condition

Cited by 12 publications

References 42 publications

Trinuclear dioxidomolybdenum(vi) complexes derived from benzene-1,3,5-tricarbohydrazide and study of the catalytic activity

Trinuclear dioxidomolybdenum(vi) complexes derived from benzene-1,3,5-tricarbohydrazide and study of the catalytic activity

Influence of Coordination Geometry on the Ring Opening of Benzoxazine: Oxidovanadium(V), Dioxidomolybdenum(VI) and Dioxidotungsten(VI) Complexes of Benzoxazine Based Ligands and their Bio Inspired Catalytic Applications

Catalytic Potential of Pyrazolone Based Dioxidomolybdenum(VI) Complexes for Multicomponent Biginelli Reactions, Epoxidation of Olefins and Oxidative Bromination of Phenol Derivatives

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