Heterocyclic Building Blocks-Benzisoxazole

Product Details of 3326-71-4. 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 Microwave-Assisted TBHP-Mediated Synthesis of 2-Amino-1,3,4-oxadiazoles in Water. Author is Kumar Sigalapalli, Dilep; Kadagathur, Manasa; Sujat Shaikh, Arbaz; Jadhav, Govinda S.; Bakchi, Bulti; Nagendra Babu, Bathini; Tangellamudi, Neelima D..

A one-pot synthesis of 2-amino-1,3,4-oxadiazoles I [R1 = Ph, 4-FC6H4, 3-furylmethyl, etc.; R2 = Ph, 3-HOC6H4, 3-BrC6H4, etc.] was achieved from the corresponding isothiocyanates and hydrazides in the presence of tert-Bu hydroperoxide (TBHP) and water under microwave irradiation The thiosemicarbazides intermediate could be derived in situ which underwent an intramol. cyclodesulfurization under microwave irradiation Apart from being simpler and green, this method offered significant advantages, such as short reaction times, economy and no requirement for a catalyst, with easy workup procedures to afford a variety of 2-amino-1,3,4-oxadiazoles I in significantly high yields (85-98%). Spectroscopic techniques were employed to elucidate the chem. structures of the final compounds and ESI-MS technique was employed to establish the formation of thiosemicarbazide intermediate and requirement of oxygen source for the completion of reaction and the most plausible reaction mechanism.

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

The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 2-Furoic hydrazide( cas:3326-71-4 ) is researched.Synthetic Route of C5H6N2O2.Neethu, K. S.; Eswaran, Jayanthi; Theetharappan, M.; Bhuvanesh, Nattamai S. P; Neelakantan, M. A.; Velusamy, Kaveri M. published the article 《Organoruthenium (II) complexes featuring pyrazole-linked Schiff base ligands: Crystal structure, DNA/BSA interactions, cytotoxicity and molecular docking》 about this compound( cas:3326-71-4 ) in Applied Organometallic Chemistry. Keywords: ruthenium arene half sandwich pyrazole Schiff base complex preparation; DNA protein intercalation ruthenium arene pyrazole Schiff base complex; crystal structure ruthenium arene pyrazole Schiff base complex; mol structure ruthenium arene pyrazole Schiff base complex. Let’s learn more about this compound (cas:3326-71-4).

Half-sandwiched ruthenium (II) arene complexes with piano stool-like geometry with the general formula [(p-cymene)RuClL1] and [(p-cymene)RuClL2] [where L1 = (Z)-N’-((1,3-diphenyl-1H-pyrazol-4-yl)methylene)furan-2-carbohydrazide and L2 = (Z)-N’-((1,3-diphenyl-1H-pyrazol-4-yl)methylene)thiophene-2-carbohydrazide] were synthesized and characterized. The single crystal X-ray data revealed that the complexes belong to the same crystal system (monoclinic) with octahedral geometry, where the ruthenium atom is surrounded by hydrazone ligand coordinated through ON atoms, one chloride labile co-ligand and the remaining three coordination sites covered by an electron cloud of p-cymene moiety. The interaction between the complexes and DNA/bovine serum albumin (BSA) was evaluated using absorption and emission titration methods showing intercalative modes of interaction. The DNA cleavage ability of the complexes was checked by agarose gel electrophoresis method exhibiting the destruction of DNA duplex arrangement. To understand the interaction between ruthenium complex and DNA/BSA mol., mol. docking studies were performed. In vitro cytotoxicity of the complexes was examined by the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay on human lung cancer cell line, A549, and found that at lower IC50, cell growth inhibition has occurred. Similarly, the IC50 values of the complexes treated with cancerous cell lines have produced a significant amount of lactase dehydrogenase and nitrite content in the culture medium, which were evaluated as apoptosis-inducing factors, suggesting that the ruthenium (II) arene hydrazone complexes with pyrazole ligands have promising anticancer activities.

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Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

Application of 3326-71-4. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: 2-Furoic hydrazide, is researched, Molecular C5H6N2O2, CAS is 3326-71-4, about Phosphine-Free Ruthenium Complex-Catalyzed Synthesis of Mono- or Dialkylated Aryl Hydrazides via the Borrowing Hydrogen Strategy. Author is Joly, Nicolas; Bettoni, Leo; Gaillard, Sylvain; Poater, Albert; Renaud, Jean-Luc.

A diaminocyclopentadienone ruthenium tricarbonyl complex-catalyzed synthesis of mono- or dialkylated aryl hydrazides from N-unsubstituted aryl hydrazides and various substituted primary and secondary alcs. as alkylating reagents using the borrowing hydrogen strategy has been developed. Deuterium labeling experiments confirmed that the alcs. are the hydride source in this cascade process. D. functional theory (DFT) calculations unveiled the origin and the threshold between the mono- and dialkylation.

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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, Research Support, N.I.H., Extramural, Research Support, Non-U.S. Gov’t, Organic Letters called Divergent Reactivity during the Trapping of Benzynes by Glycidol Analogs: Ring Cleavage via Pinacol-Like Rearrangements vs Oxirane Fragmentations, Author is Zhang, Juntian; Hoye, Thomas R., which mentions a compound: 37443-42-8, SMILESS is O=C(C1OCCC1)OC, Molecular C6H10O3, Quality Control of Methyl tetrahydrofuran-2-carboxylate.

Hydroxy-containing cyclic ethers react with thermally generated benzynes to produce aryl ethers. Diverse reactivity was observed Cleavage of the cyclic ether was involved in most of the pathways. The transformations are rationalized via initial formation of oxonium ion-containing 1,3-zwitterions arising from preferential nucleophilic attack on the benzyne by the ether oxygen. Pinacol-like rearrangements, including ring expansion, to yield aldehydes or ketones and oxirane fragmentations to generate aryl enol ethers were main competing events.

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Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: cis-Cyclohexane-1,2-dicarboxylic acid(SMILESS: O=C([C@H]1[C@@H](C(O)=O)CCCC1)O,cas:610-09-3) is researched.Reference of 2-Furoic hydrazide. The article 《The ionization of aliphatic dicarboxylic acids in water》 in relation to this compound, is published in Journal of Solution Chemistry. Let’s take a look at the latest research on this compound (cas:610-09-3).

Potentiometric, calorimetric, and dilatometric data on the ionization of several saturated dicarboxylic acids in water at 25° are reported. A correlation is attempted between structure and thermodn. evidences for the two dissociation stages of the diacids considered, in particular in terms of the propensity toward intramol. H bond formation of some singly ionized species.

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Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

Reference of 2-Furoic hydrazide. 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 Lemon Juice as a Biocatalyst Under Ultrasound Irradiation: Synthesis and Pharmacological Evaluation of 2-amino-1,3,4-thiadiazoles. Author is Prasad, Malavattu G.; Lakshmi, Chapala V.; Katari, Naresh K.; Pal, Manojit.

An ultrasound-assisted method facilitated by lemon juice has been developed to synthesize 2-amino-1,3,4-thiadiazole derivatives I (Ar = Ph, 2-methoxy-5-nitrophenyl, pyridin-3-yl, etc.) that could act as potential anticancer agents. Accordingly, a convenient method has been developed for the rapid synthesis of this class of compounds I under a mild and non-hazardous reaction condition in good yields. The methodol. involved the reaction of various acid hydrazides ArC(O)NHNH2 with TMSNCS in the presence of lemon juice in PEG-400 at room temperature (25-30°C) under ultrasound irradiation These compounds I were assessed for their cytotoxic properties against two different metastatic breast cancer cell lines e.g., MDAMB-231 and MCF-7 and subsequently against SIRT1. The 2-amino 1,3,4-thiadiazole derivatives I (Ar = 4-methoxyphenyl, 3-methoxyphenyl, 2,3-dimethoxyphenyl, 2-methoxy-5-nitrophenyl) showed promising growth inhibition of MDAMB- 231 and MCF-7 cell lines and SIRT1 inhibition in vitro. Indeed, I (Ar = 3-methoxyphenyl) was found to be a potent inhibitor of SIRT1.

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

Gamov, G. A.; Khodov, I. A.; Belov, K. V.; Zavalishin, M. N.; Kiselev, A. N.; Usacheva, T. R.; Sharnin, V. A. published the article 《Spatial structure, thermodynamics and kinetics of formation of hydrazones derived from pyridoxal 5′-phosphate and 2-furoic, thiophene-2-carboxylic hydrazides in solution》. Keywords: pyridoxal phosphate hydrazone conformer hydrolysis kinetics overhauser effect.They researched the compound: 2-Furoic hydrazide( cas:3326-71-4 ).Application of 3326-71-4. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:3326-71-4) here.

The spatial structure of pyridoxal 5′-phosphate hydrazones of 2-furoic hydrazide; thiophene-2-carboxylic hydrazide in aqueous solution was studied by means of quantum chem. calculations and NOE experiment The hydrazones could exist as a mixture of different conformers; however, the specific ones could be suggested from exptl. and calculated data. The stability constants of hydrazones at pH of 1.9; 6.6; 7.0; 7.4 were determined using UV-Vis spectroscopy. Rate constants of the hydrazone formation and hydrolysis reaction within the range of 6.6-7.4 pH were obtained. Isothermal calorimetric titration was performed in order to determine the change in the free Gibbs energy, enthalpy and entropy of hydrazones formation at pH of 6.6. Hydrazones were synthesized and characterized by means of 1H, 13C, 31P NMR, IR, UV-Vis, fluorescent, MS-spectroscopy as well as DSC and elemental anal.

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

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Stereoisomeric biologically active compounds. I. Some conversions of cis-4-chloro-4-cyclohexene-1,2-dicarboxylic acid》. Authors are Rashidyan, L. G.; Tatevosyan, G. T..The article about the compound:cis-Cyclohexane-1,2-dicarboxylic acidcas:610-09-3,SMILESS:O=C([C@H]1[C@@H](C(O)=O)CCCC1)O).Category: benzisoxazole. Through the article, more information about this compound (cas:610-09-3) is conveyed.

cf. Baeyer, Ann. Chem. 258, 215(1890); U.S. 1,967,862, CA 28, 5994. To 10 g. cis-4-chloro-4-cyclohexene-1,2-dicarboxylic acid (I) and 60 ml. H2O, under cooling and stirring, a solution of 21 g. KMnO4 in 650 650 ml. H2O was added over 3 hrs. The cooling and stirring was another 2 hrs. and the mixture left standing overnight, yielding meso-butane-1,2,3,4-tetracarboxylic acid m. 191-2°. I (204.5 g.) and 15 ml. concentrated H2SO4 in 500 ml. absolute MeOH was refluxed for 8 hrs. Dimethyl cis-4-chloro-4-cyclohexene-1,2-dicarboxylate (II), b5 148-50°, d204 1.0553, n20D 1.4935 was obtained in 71.3% yield. II (20 g.) and 18 ml. 85% H2NNH2 was refluxed for 3 hrs. Trans-4-chloro-4-cyclohexene-1,2-dicarboxylic acid dihydrazide (III) m. 222-4° (60% EtOH) was obtained in 69.5% yield. To 30 g. III in 105 ml. 10% HCl and 280 ml. CH2Cl2 at 18-20°, a solution of 20.8 g. NaNO3 in 48.5 ml. H2O was slowly added. The nonaqueous layer was dried, filtered, and treated with 160 ml. absolute EtOH. The CH2Cl2 was evaporated, the mixture refluxed for 2 hrs., 210 ml. 40% NaOH added and steam distilled The distillate was acidified with 10% HCl giving the trans-4-chloro-1,2-diamino-4-cyclohexene-2HCl m. 326-8° in 72.1% yield. III (38 g.) and a solution of 26.6 g. NaOH in 350 ml. H2O was refluxed for 12 hrs. and acidified, giving trans-4-chloro-4-cyclohexene-1,2-dicarboxylic acid (IV) m. 115-17° (H2O) in 89.8% yield. IV (10 g.) was oxidized with KMnO4 as described above, giving the dianhydride of dl-butane-1,2,3,4-tetracarboxylic acid m. 172-3°. A solution of 21 g. IV, 8 g. NaOH and 70 ml. H2O was hydrogenated in an autoclave in the presence of 35 g. Ni on Cr2O3 at 100° and 100 atm. The solution was filtered and acidified giving trans-cyclohexane-1,2-dicarboxylic acid (V) m. 220° (Me2O) in 78.2% yield. I (60 g.) and 23.5 g. NaOH in 200 ml. H2O was hydrogenated as described above giving cis-cyclohexane-1,2-dicarboxylic acid (VI), m. 192°, in 92.1% yield. A mixture of 8 g. VI and 20 ml. concentrated HCl was heated in a sealed tube at 180° for 8-10 hrs. and V, m. 220-1°, was obtained in 88.8% yield.

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Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

In general, if the atoms that make up the ring contain heteroatoms, such rings become heterocycles, and organic compounds containing heterocycles are called heterocyclic compounds. An article called Synthesis, characterization, and nonlinear optical properties of some new series of S-(5-aryl-1,3,4-oxadiazol-2-yl)-2-chloroethanethioate derivatives, published in 2019, which mentions a compound: 3326-71-4, Name is 2-Furoic hydrazide, Molecular C5H6N2O2, Electric Literature of C5H6N2O2.

In the present investigation, some novel S-(5-aryl-1,3,4-oxadiazol-2-yl)-2-chloroethanethioate I [Ar = Ph, 2-ClC6H4, 2-furanyl, 2-O2NC6H4, 3-O2NC6H4] derivatives were synthesized and their impact on optical properties was studied. The nonlinear refractive indexes of compounds I were also measured in dichloromethane via Z-scan method using a continuous wave diode-pumped laser at 532 nm wavelength. The nonlinear refractive coefficient of compounds I was obtained from 1011 m2/W order. Regarding the appropriate nonlinearity of these compounds, they could be considered good candidates for biooptical and photonic applications. All the synthesized compounds I were also evaluated for their antibacterial and antifungal activities. The bioactive assay showed that the synthetic compounds displayed variable inhibition zones against tested bacterium Escherichia coli and fungus Aspergillus fumigatus in comparison to enrofloxacin and amphotericin as reference drugs, which are normally used for treating such infections. Synthesized compounds were characterized by elemental anal. and various spectroscopic methods including FTIR, 1H NMR, 13C NMR and UV-Vis techniques.

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Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

SDS of cas: 610-09-3. 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: cis-Cyclohexane-1,2-dicarboxylic acid, is researched, Molecular C8H12O4, CAS is 610-09-3, about An Open-Framework Material with Dangling Organic Functional Groups in 24-Ring Channels. Author is Zhu, Jin; Bu, Xianhui; Feng, Pingyun; Stucky, Galen D..

An open-framework material with dangling organic functional groups in 24-ring channels, Zn3(O3PCH2CO2)2(O3PCH2CO2H)(NH3CH2CH2NH3)(BTC) (BTC = 1,3,5-benzenetricarboxylic acid), was prepared and its crystal structure was determined The material with a tetrahedral zeolite-type structure belongs to space group R3̅, Z = 18, a 41.663(7), c 7.843(2)Å, R = 7.43, Rw = 19.7%. Each O3PCH2CO2 group behaves like a regular PO43- group in zeolite-type frameworks and is 4-connected to 4 Zn sites; 2 of the 3 unique Zn sites are 4-connected to P atoms sites. The 3rd Zn site is pentacoordinated to 5 O atoms and 3-connected to P sites because 2 pairs of O atoms are chelating O atoms from 2 O3PCH2CO2 groups.

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