Controlled Modification of Triaminoguanidine-Based μ3 Ligands in Multinuclear [VIVO]/[VVO2] Complexes and Their Catalytic Potential in the Synthesis of 2-Amino-3-cyano-4H-pyrans/4H-chromenes

Maurya, Mannar R.; Kumar, Naveen; Avecilla, Fernando

doi:10.1021/acs.inorgchem.3c03704

Cited by 3 publications

(3 citation statements)

References 110 publications

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“…Finally, ACPs were formed from intermediate IV via a hydrogen atom rearrangement reaction. Similar pathways of the reaction were also suggested by Magyar et al, Ebrahimiasl et al, and Maurya et al ,, for one-pot multicomponent reactions.…”

Section: Resultssupporting

confidence: 83%

“…Since the compound containing 4 H -pyrans has outstanding biological properties and pharmaceutical applications, several synthetic methods have now been published in the literature − using several catalysts, such as carbon-based solid acids, montmorillonite perchloric acid (MPA), MgO NPs, Zn( l -proline) 2 , cyclodextrin, THEIC-SBA-15, urea, TMDPS, Fe 3 O 4 @D-NH-(CH 2 ) 4 -SO 3 H, TiO 2 –CNT nanocomposite, [BMIm]BF 4 , Na 2 CO 3 , Mo catalyst, nano-TiO 2 /H 14 [NaP 5 W 30 O 110 ], V-complex, [HMIM]C(CN) 3 , trifluoroethylene (TFE), supported-KF, urea, nanozeolite, Fe 3 O 4 @SiO 2 -imid–PMA, etc. Undoubtedly, these reported methods have their advantages.…”

Section: Introductionmentioning

confidence: 99%

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Ni–Unsymmetrical Salen Complex-Catalyzed One-Pot Multicomponent Reactions for Efficient Synthesis of Biologically Active 2-Amino-3-cyano-4H-pyrans

Patra,

Nandi,

Maurya

et al. 2024

ACS Omega

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In this report, four new Ni(II)−unsymmetrical salen complexes, [NiL 1−4 ], were prepared by refluxing Ni(Ac) 2 •4H 2 O with unsymmetrical salen ligands, H 2 L 1−4 . All of the synthesized ligands and complexes were characterized by various physicochemical methods. Also, the solid-state structures of [NiL 1 ], [NiL 2 ], and [NiL 4 ] were defined through single-crystal X-ray diffraction methods. The catalytic potential of [NiL 1−4 ] was investigated by economic and environmentally friendly one-pot-three-component reactions (using reagent: 1,3-dicarbonyls, malononitrile, benzaldehyde, or its derivatives) for the synthesis of biologically active 2amino-3-cyano-4H-pyran derivatives (total 16 derivatives). After optimization of the reaction conditions, this new synthetic protocol by taking Ni(II)−unsymmetrical salen complexes as catalysts shows excellent conversion with a maximum yield of up to 98% of the effective catalytic products within 1 h of reaction time. In addition, it was observed that the aromatic aldehyde containing an electron-withdrawing group as a ring substituent shows better conversion (up to 98%), and the electron-donating group substituent shows similar or less conversion compared to benzaldehyde under the optimized reaction conditions. From the comparison of results between all these Ni complexes, it was found that the efficiency of the catalytic performance follows the order [NiL 1 ] > [NiL 3 ] > [NiL 2 ] > [NiL 4 ]. A possible reaction pathway was predicted and established through UV−vis spectroscopy. Intermediate II proposed in the reaction pathway was also trapped and characterized through 1 H and 13 C NMR.

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Section: Resultssupporting

confidence: 83%

Section: Introductionmentioning

confidence: 99%

Ni–Unsymmetrical Salen Complex-Catalyzed One-Pot Multicomponent Reactions for Efficient Synthesis of Biologically Active 2-Amino-3-cyano-4H-pyrans

Patra,

Nandi,

Maurya

et al. 2024

ACS Omega

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“…Based on the proposed reaction mechanism in literature [64,69] carbonyl group of aromatic aldehydes gets activated via hardhard (HH) interaction with molybdenum metal centre. Then, activated aromatic aldehyde reacts with malononitrile via Knoevenagel condensation to give intermediate (i).…”

Section: Reactivity Study Of Binuclear Dioxidomolybdenum(vi) Complex ...mentioning

confidence: 99%

Polymer Supported Nitrogen‐Bridged Symmetrical Binuclear Dioxidomolybdenum(VI) Complexes and Their Homogeneous Analogues as Potential Catalysts for Efficient Synthesis of 2‐Amino‐3‐Cyano‐4H‐Chromenes/Pyrans

Maurya,

Nandi,

Kumar

et al. 2024

Chemistry A European J

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Reaction of 2‐chloromethylbenzimidazole with known intermediates (i – iii), prepared from diaminoguanidine hydrochloride with salicylaldehyde, 5‐bromo‐salicylaldehyde or 3,5‐di‐tert‐butylsalicylaldehyde, led to the formation of benzimidazole appended new ligands, H4L1–H4L3 (I−III). The homogeneous nitrogen‐bridged symmetrical binuclear complexes, [(MoVIO2)2(L1)(H2O)2] (1), [(MoVIO2)2(L2)(H2O)2] (2) and [(MoVIO2)2(L3)(MeOH)2] (3) and mononuclear complexes, [MoVIO2(H2L1)(MeOH)] (4), [MoVIO2(H2L2)(H2O)] (5) and [MoVIO2(H2L3)(MeOH)] (6).have been isolated by reacting these ligands. The corresponding binuclear heterogeneous compounds [(MoVIO2)2(L1)(DMF)2]@PS (PS‐1), [(MoVIO2)2(L2)(DMF)2]@PS (PS‐2) and [(MoVIO2)2(L3)(DMF)2]@PS (PS‐3) have been obtained by immobilization of 1−3 onto chloromethylated polystyrene beads. All synthesized ligands, homogeneous as well as heterogeneous supported compounds have been characterized well. Heterogeneous compounds (PS‐1−PS‐3) have further been studied by microwave plasma atomic emission spectroscopy, X‐ray photoelectron spectroscopy, and field emission scanning electron microscopy along with energy dispersive spectroscopy. All compounds were explored for catalytic applications to one‐pot multicomponent reactions (MCRs) for efficient synthesis of biologically active 2‐amino‐3‐cyano‐4H‐chromenes/pyrans (21 examples). Optimizing various reaction parameters helped in achieving as high as 97% yields of products. Though, only half equivalent of the binuclear complexes (1‐3) was required compared to mononuclear analogues (4‐6) to achieve comparable yields, heterogeneous catalysts have an added advantage due to their stability and recyclability. Suitable reaction mechanism has also been proposed based on isolated intermediate(s).

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Nonoxidovanadium(IV) Complex-Catalyzed Synthesis of 2-Amino-3-cyano-4H-pyrans/4H-chromenes, Biscoumarins, and Xanthenes under Green Conditions

Maurya,

Kumar

et al. 2024

J. Org. Chem.

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Reaction of [V IV O(acac) 2 ] (Hacac = acetylacetone) with a Mannich base, N,N,N′, N′-tetrakis(2-hydroxy-3,5-di-tert-butyl benzyl)-1,2-diaminoethane (H 4 L, I) in a 1:1 molar ratio in MeOH, leads to the formation of the nonoxidovanadium(IV) complex [V IV L] (1). Air stable complex 1 has been characterized using various spectroscopic techniques, DFT calculations, and single-crystal X-ray studies. 1 adopts distorted octahedral geometry where ligand coordinates through all coordination functionalities available. This complex has been used as a catalyst in the one-pot, three-component synthesis of 2-amino-3-cyano-4H-pyrans using 1,3-dicarbonyls (1,3-cyclohexanedione, dimedone, barbituric acid, and 4-hydroxycoumarin), malononitrile, and various substituted aromatic aldehydes in equimolar amounts employing ethanol as a green solvent. The catalytic reaction revealed that the multicomponent synthesis of 4H-pyrans and chromenes is greatly influenced by both types of 1,3-dicarbonyl compound employed and the nature of the substituent on the aromatic ring of the aldehyde. Synthesized catalyst has also been used in the synthesis of pharmacologically relevant oxygen-containing heterocycles, specifically, 1,8-dioxo-octahydro-1H-xanthenes and biscoumarins. The possible mechanism for the synthesized one-pot, multicomponent product has been proposed by isolating intermediate(s) generated during synthesis.

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Controlled Modification of Triaminoguanidine-Based μ₃ Ligands in Multinuclear [V^IVO]/[V^VO₂] Complexes and Their Catalytic Potential in the Synthesis of 2-Amino-3-cyano-4H-pyrans/4H-chromenes

Cited by 3 publications

References 110 publications

Ni–Unsymmetrical Salen Complex-Catalyzed One-Pot Multicomponent Reactions for Efficient Synthesis of Biologically Active 2-Amino-3-cyano-4H-pyrans

Ni–Unsymmetrical Salen Complex-Catalyzed One-Pot Multicomponent Reactions for Efficient Synthesis of Biologically Active 2-Amino-3-cyano-4H-pyrans

Polymer Supported Nitrogen‐Bridged Symmetrical Binuclear Dioxidomolybdenum(VI) Complexes and Their Homogeneous Analogues as Potential Catalysts for Efficient Synthesis of 2‐Amino‐3‐Cyano‐4H‐Chromenes/Pyrans

Nonoxidovanadium(IV) Complex-Catalyzed Synthesis of 2-Amino-3-cyano-4H-pyrans/4H-chromenes, Biscoumarins, and Xanthenes under Green Conditions

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