Category: 3326-71-4

Maurya, Mannar R.; Jangra, Nancy; Avecilla, Fernando; Correia, Isabel published an article about the compound: 2-Furoic hydrazide( cas:3326-71-4,SMILESS:O=C(C1=CC=CO1)NN ).Product Details of 3326-71-4. Aromatic heterocyclic compounds can be classified according to the number of heteroatoms or the size of the ring. The authors also want to convey more information about this compound (cas:3326-71-4) through the article.

Four ONO donor ligands are isolated from the condensation of 4,6-diacetyl resorcinol with isonicotinoyl hydrazide (H2dar-inh, I), nicotinoyl hydrazide (H2dar-nah, II), benzoyl hydrazide (H2dar-bhz, III), and 2-furoyl hydrazide (H2dar-fah, IV) on refluxing in MeOH. The reaction of in situ generated aqueous K[H2VVO4] with ligands I-IV at neutral pH gives complexes [K(H2O)2][VO2(dar-inh)] (1), [K(H2O)2][VO2(dar-nah)] (2), [K(H2O)2][VO2(dar-bhz)] (3), and [K(H2O)2][VO2(dar-fah)] (4), resp. The reaction of [VIVO(acac)2] (acac = acetylacetonato) with these ligands (I-IV) under aerobic conditions in methanol yields oxidomethoxidovanadium(V) complexes [VO(OMe)(MeOH)(dar-inh)] (5), [VO(OMe)(MeOH)(dar-nah)] (6), [VO(OMe)(MeOH)(dar-bhz)] (7), and [VO(OMe)(MeOH)(dar-fah)] (8). All the isolated complexes are characterized by elemental, thermal, electrochem., and spectroscopic techniques [FTIR, UV/Vis, NMR (1H, 13C and 51 V NMR)], and single-crystal X-ray diffraction anal. (for 1, 6, 7, and 8). X-ray anal. confirms the coordination of the ligands through Ophenolate, Nazomethine, and Oenolate to the metal center. In the mol. structure of [K(H2O)(EtOH)][VVO2(dar-inh)] (abbreviated as 1a where one mol. of water is replaced by EtOH), water mols. act as bridges between two K+ ions and the complex shows a dimeric structure due to the presence of electrostatic interactions between V=O oxygen atoms with K+ ions. These complexes are active catalysts for the oxidative bromination of thymol in the presence of KBr, HClO4, and H2O2 and give 2-bromothymol, 4-bromothymol, and 2,4-dibromothymol as major products. Complexes 1-4 were also tested as catalysts for the epoxidation of various alkenes (namely styrene, cyclohexene, cis-cyclooctene, 1-hexene, 1-octene, cyclohexenone, and trans-stilbene) with H2O2 in the presence of NaHCO3 as promoter, giving the corresponding epoxides selectively.

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Reference:
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

Application In Synthesis of 2-Furoic hydrazide. The protonation of heteroatoms in aromatic heterocycles can be divided into two categories: lone pairs of electrons are in the aromatic ring conjugated system; and lone pairs of electrons do not participate. Compound: 2-Furoic hydrazide, is researched, Molecular C5H6N2O2, CAS is 3326-71-4, about Direct Catalytic Symmetrical, Unsymmetrical N,N-Dialkylation and Cyclization of Acylhydrazides Using Alcohols. Author is Thiyagarajan, Subramanian; Gunanathan, Chidambaram.

Herein, direct N,N-dialkylation of acylhydrazides using alcs. is reported. This catalytic protocol provides one-pot synthesis of both sym. and unsym. N,N-disubstituted acylhydrazides using an assortment of primary and secondary alcs. with remarkable selectivity and excellent yields. Interestingly, the use of diols resulted in intermol. cyclization of acylhydrazides, and such products are privileged structures in biol. active compounds Water is the only byproduct, which makes this catalytic protocol sustainable and environmentally benign.

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Reference:
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

Reference of 2-Furoic hydrazide. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: 2-Furoic hydrazide, is researched, Molecular C5H6N2O2, CAS is 3326-71-4, about A transition metal-free approach towards synthesis of β-carboline tethered 1,3,4-oxadiazoles via oxidative C-O bond formation. Author is Singh, Dharmender; Tiwari, Sandip Kumar; Singh, Virender.

An efficient protocol were developed for one-pot synthesis of biol. interesting β-carboline substituted 1,3,4-oxadiazoles via an I2-assisted oxidative C-O bond formation strategy. This metal-free sequential approach was found to be compatible with diversely substituted 1-formyl β-carbolines and aromatic as well as aliphatic hydrazides, providing access to a variety of multifunctional β-carboline linked 1,3,4-oxadiazole derivatives in good to excellent yields. The methodol. was found to be applicable to gram scale synthesis of β-carboline substituted 1,3,4-oxadiazole derivatives Addnl., β-carboline C1 linked 2-amino-1,3,4-oxadiazoles and bis-1,3,4-oxadiazoles were also synthesized using the same strategy.

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Reference:
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

Quality Control of 2-Furoic hydrazide. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: 2-Furoic hydrazide, is researched, Molecular C5H6N2O2, CAS is 3326-71-4, about Synthesis, crystal structures, and characterization of three zinc complexs with different acylhydrazone-type schiff base ligands. Author is Xie, Qing-fan; Chen, Yan-min.

Three zinc complexes, namely [Zn(Lss)(phen)(DMF)] (1), {[Zn (HLdis)]2·2CH3OH}n (2) and [Zn(Baf)2]·CH3OH (3), formed from different acylhydrazone-type Schiff base ligands were synthesized by using different methods, and the compounds were characterized by IR, UV-Vis spectra and TGA. The X-ray diffraction analyses revealed that 1 and 3 crystallized in the triclinic space group P1̅ while 2 in monoclinic system space group P21/n. In 1 and 3, coordination number of the Zn (II) was six, and the centric atom located in a distorted octahedron geometry, while in 2 Zn (II) was five-coordination in a distorted square-pyramidal geometry. The precursor of 3 was pyrazoline derivative with the formula C15H14N2O3 (Pzl) crystallizing in monoclinic system space group P21/c. Due to the coordination of Zn (II) causing the intramol. rearrangement of Pzl, the ring open product HBaf in the form of an acylhydrazone structure coordinated with Zn (II) to form complex 3.

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Reference:
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Article, Journal of Asian Natural Products Research called Design and synthesis of 7-diethylaminocoumarin-based 1,3,4-oxadiazole derivatives with anti-acetylcholinesterase activities, Author is Yu, Xiang; Zhao, You-Fang; Huang, Guo-Juan; Chen, Ya-Fang, which mentions a compound: 3326-71-4, SMILESS is O=C(C1=CC=CO1)NN, Molecular C5H6N2O2, Category: benzisoxazole.

Twelve novel 7-diethylaminocoumarin-based 1,3,4-oxadiazole derivatives I [R = n-Bu, 2-thienyl, Ph, etc.] were synthesized via iodine-mediated oxidative cyclization and confirmed by 1H NMR, 13C NMR and HRMS. The synthesized derivatives I were tested against in-vitro acetylcholinesterase inhibitory activity and results showed that compounds I [R = 4-ClC6H4, 4-BrC6H4] exhibited moderate inhibitory activities with 69.19% and 65.06%, resp. The preliminary structure-activity relationships revealed that introduction of halogen atom on the para-position of Ph of compounds I could enhance their activities. Mol. docking study suggested that compound I [R = ClC6H4] possessed an optimal docking pose with interactions inside AChE.

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Reference:
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

SDS of cas: 3326-71-4. The protonation of heteroatoms in aromatic heterocycles can be divided into two categories: lone pairs of electrons are in the aromatic ring conjugated system; and lone pairs of electrons do not participate. Compound: 2-Furoic hydrazide, is researched, Molecular C5H6N2O2, CAS is 3326-71-4, about Mononuclear and binuclear dioxidomolybdenum(VI) complexes of ONO appended aroylhydrazone: Crystal structures, interaction energy calculation and cytotoxicity. Author is Kuriakose, Daly; Kurup, M. R. Prathapachandra.

Mono- and binuclear cis-MoO2 complexes (1-3) [MoO2(ISF)D] (D = H2O 1, DMSO 2 and 4,4′-bipyridine 3; ISF = 3,5-diiodosalicyaldehyde-2-furoichydrazone) were synthesized and fully characterized by different physicochem. methods. The mol. structures were confirmed unambiguously by single crystal x-ray diffraction studies. The octahedral geometry around the Mo(VI) central atom is satisfied by O, N, O donor atoms of dideprotonated dianionic hydrazone moiety, two oxido oxygens and O/N atoms of the coordinated solvent mols. The asym. unit of complexes 1 and 2 contains one mol. whereas complex 3 contains only half of the mol. The 4,4′-bipyridine mol. acts as a linker that links the two asym. MoO2D moieties to form the binuclear dioxidomolybdenum(VI) in complex 3 with Mo···Mo nonbonding distance of 12.01(10) Å. The relevance of H bonding and nonbonding interactions in the construction of supramol. architectures were studied. The upshots of single crystal studies were reproduced with the aid Hirshfeld surface studies. The pre-eminence of dispersion energy component over other components was established by interaction energy calculations and the energy framework anal. The average interaction energy values for complexes 2 and 3 are -282.3 and -228.3 kJ mol-1, resp. Also the in vitro cytotoxicity of all the synthesized compounds was evaluated against lymphoma ascites cell line.

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Reference:
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

Formula: C5H6N2O2. The protonation of heteroatoms in aromatic heterocycles can be divided into two categories: lone pairs of electrons are in the aromatic ring conjugated system; and lone pairs of electrons do not participate. Compound: 2-Furoic hydrazide, is researched, Molecular C5H6N2O2, CAS is 3326-71-4, about Kinetic and mechanistic analysis of oxidation of 2-furoic hydrazide by hexachloroirradate(IV) in a wide pH range. Author is Yao, Haiping; Tian, Hongwu; Xu, Liyao; Xia, Yanqing; Zhou, Li; Liu, Chunli; Shi, Tiesheng.

Oxidation of 2-furoic hydrazide (FH) by hexachloroiridate(IV) ([IrCl6]2-) was studied kinetically in a wide pH range in aqueous solution of 1.0 M ionic strength. The oxidation reaction followed well-defined second-order kinetics: – d[IrCl62-]/dt = k'[FH]tot[IrCl62-], where [FH]tot denotes the total concentration of FH and k’ stands for the observed second-order rate constants The established k’-pH profile displays that k’ increases drastically with pH and a plateau region exists between pH 4 and 6. A stoichiometric ratio of Δ[FH]tot/Δ[IrCl62-] = 1/4 was revealed by spectrophotometric titrations 1H NMR spectroscopic studies indicated that FH was cleanly oxidized to 2-furoic acid. The kinetic data suggest a reaction mechanism in which all the three protolysis species of FH react with [IrCl6]2- in parallel, forming the rate-determining steps. Two stabilized hydrazyl radicals are generated in the rate-determining steps, in which a single electron is transferred to [IrCl6]2-. The two hydrazyl radicals react rapidly in consecutive steps requiring 3 mol of Ir(IV) to form 2-furoic acid as the final product. Rate constants of the rate-determining steps were deduced through a simulation of the rate expression to the k’-pH dependency data. Values of these rate constants demonstrate that the three protolysis species of FH have a huge reactivity span, changing by about 109 times toward reduction in [IrCl6]2- and that FH can be readily oxidized in neutral and basic media. Rapid scan spectra and the measured activation parameters suggest that an outer-sphere electron transfer is probably taking place in each of the rate-determining steps. This is the first kinetic study on the oxidation reactions of FH and provides concurrently the protolysis constants of FH (pKa1 = 3.04 ± 0.08 and pKa2 = 11.6 ± 0.1) at 25.0 °C and 1.0 M ionic strength.

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Reference:
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: 2-Furoic hydrazide, is researched, Molecular C5H6N2O2, CAS is 3326-71-4, about A highly selective fluorescent sensor for Ca2+ and Sr2+ based on diarylethene with a furan-carbohydrazide unit, the main research direction is fluorescent sensor calcium strontium diarylethene furan carbohydrazide.Safety of 2-Furoic hydrazide.

A fluorescent sensor based on diarylethene (I) has been designed and synthesized. The sensor not only exhibited excellent photochromic properties, but also has distinguishing ability for Ca2+ and Sr2+ from other metal ions. Upon addition of Ca2+ and Sr2+, its emission intensity enhanced 27-fold and 24-fold resp., accompanied by the emission peak shifted from 439 nm to 484 nm for Ca2+, and to 479 nm for Sr2+. The 1:1 stoichiometry between the sensor and the two ions was confirmed by Job’s plot and HRMS. The LOD for Ca2+ and Sr2+ was determined to be 9.4 × 10-8 mol L-1 and 7.2 × 10-8 mol L-1, resp. Furthermore, the sensor was applied in the detection of Ca2+ and Sr2+ in practical samples successfully.

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Reference:
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

Synthetic Route of C5H6N2O2. The reaction of aromatic heterocyclic molecules with protons is called protonation. Aromatic heterocycles are more basic than benzene due to the participation of heteroatoms. Compound: 2-Furoic hydrazide, is researched, Molecular C5H6N2O2, CAS is 3326-71-4, about Green aqueous synthesis and antimicrobial evaluation of 3,5-disubstituted 1,2,4-triazoles. Author is Beyzaei, Hamid; Malekraisi, Farideh; Aryan, Reza; Ghasemi, Behzad.

An eco-friendly and simple procedure was proposed for the synthesis of 3,5-disubstituted 1,2,4-triazoles I [R = Ph, 4-pyridyl, 2-furyl, etc.] by optimized reaction of benzamidine hydrochloride and various aryl hydrazides. The products were generated in good to high yields in one step and sufficient purity after a simple workup. Inhibitory activity of all prepared derivatives was evaluated against 10 pathogenic bacterial strains including both Gram-pos. and Gram-neg., as well as 2 mold and 1 yeast strains. The prepared derivatives showed good antimicrobial activities and 1,2,4-triazoles containing 2-hydroxynaphthalen-3-yl and 5-chlorothiophen-2-yl substituents at position 3 showed the best antifungal and antibacterial properties, resp.

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Reference:
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

SDS of cas: 3326-71-4. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: 2-Furoic hydrazide, is researched, Molecular C5H6N2O2, CAS is 3326-71-4, about Iodine-promoted one-pot synthesis of 1,3,4-oxadiazole scaffolds via sp3 C-H functionalization of azaarenes. Author is Mani, Geeta Sai; Donthiboina, Kavitha; Shankaraiah, Nagula; Kamal, Ahmed.

An efficient iodine-mediated one-pot synthetic protocol for the synthesis of 2,5-disubstituted 1,3,4-oxadiazoles scaffolds I [R = 2-furyl, Ph, 4-ClC6H4, etc.; R1 = 2-pyridyl, 2-quinolinyl, 7-Clquinolin-2-yl, etc.] was developed via sp3 C-H functionalization. This method involved oxidative amination with concomitant base-mediated cyclization of methylhetarenes and acylhydrazines by employing iodine and Cs2CO3. The key features of the present method included good functional group tolerance, a clean protocol, metal-free conditions and high yields, making this protocol an attractive strategy toward the synthesis of bioactive mols. and their key building blocks.

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Reference:
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics