Heterocyclic Building Blocks-Benzisoxazole

Wu, Yuan-Yuan; Shao, Wu-Bin; Zhu, Jian-Jun; Long, Zhou-Qing; Liu, Li-Wei; Wang, Pei-Yi; Li, Zhong; Yang, Song published the article 《Novel 1,3,4-Oxadiazole-2-carbohydrazides as Prospective Agricultural Antifungal Agents Potentially Targeting Succinate Dehydrogenase》. Keywords: oxadiazolecarbohydrazide agricultural antifungal targeting succinate dehydrogenase; 1,3,4-oxadiazole; bioactivity; carbohydrazide; succinate dehydrogenase inhibitor.They researched the compound: 2-Furoic hydrazide( cas:3326-71-4 ).Recommanded Product: 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.

A novel simple 1,3,4-oxadiazole-2-carbohydrazides was reported to discover low-cost and versatile antifungal agents. Bioassay results suggested that a majority of the designed compounds were extremely bioactive against four types of fungi and two kinds of oomycetes. This extreme bioactivity was highlighted by the applausive inhibitory effects of compounds 4b, 4h, 5c, 5g, 5h, 5i, 5m, 5p, 5t, and 5v against Gibberella zeae, affording EC50 values ranging from 0.486μg/mL to 0.799μg/mL, which were superior to that of fluopyram (2.96μg/mL) and comparable to those of carbendazim (0.947μg/mL) and prochloraz (0.570μg/mL). Meanwhile, compounds 4g, 5f, 5i, and 5t showed significant actions against Fusarium oxysporum with EC50 values of 0.652, 0.706, 0.813, and 0.925μg/mL, resp. Pharmacophore exploration suggested that the N’-phenyl-1,3,4-oxadiazole-2-carbohydrazide pattern is necessary for the bioactivity. Mol. docking of 5h with succinate dehydrogenase (SDH) indicated that it can completely locate the inside of the binding pocket via hydrogen-bonding and hydrophobic interactions, revealing that this novel framework might target SDH. This result was further verified by the significant inhibitory effect on SDH activity. In addition, SEM patterns were performed to elucidate the anti-G. zeae mechanism. Given these features, this type of frameworks is a suitable template for future exploration of alternative SDH inhibitors against plant microbial infections.

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

Application In Synthesis of Methyl tetrahydrofuran-2-carboxylate. So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic. Compound: Methyl tetrahydrofuran-2-carboxylate, is researched, Molecular C6H10O3, CAS is 37443-42-8, about Cannizzaro reaction of aldehydes in TMAH thermochemolysis.

Recently, tetramethylammonium hydroxide (TMAH) was advantageously used in the anal. pyrolysis of polymers, but yielded a great amount of carboxylic acid Me esters which were absent in conventional pyrolysis. The experiments with model compounds such as furaldehyde, benzaldehyde, hydroxy-, methoxy-, dimethoxybenzaldehyde and vanillin show that TMAH can react not only as a methylating and/or hydrolyzing agent but also with aldehydes according to a Cannizzaro reaction and the reaction products can be in-situ methylated to the corresponding esters and ethers.

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Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

Name: 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 BOPAHY: a doubly chelated highly fluorescent pyrrole-acyl hydrazone -BF2 chromophore. Author is Pookkandam Parambil, Shandev; de Jong, Flip; Veys, Koen; Huang, Jianjun; Veettil, Santhini Pulikkal; Verhaeghe, Davy; Van Meervelt, Luc; Escudero, Daniel; Van der Auweraer, Mark; Dehaen, Wim.

New easily functionalisable and highly fluorescent BOPAHY chromophores were synthesized via a 1-pot two-step reaction starting from com. available pyrrole-2-carbaldehydes and resp. acyl hydrazides in the presence of BF3·OEt2. Most importantly, all BOPAHY dyes show excellent photophys. properties with quantum yields up to 0.92. Steady-state spectroscopy and quantum chem. calculations provide a first insight into these promising properties.

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Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called Application of the cyano ester ring closure to five- and six-membered rings, published in 1938, which mentions a compound: 610-09-3, mainly applied to , Category: benzisoxazole.

cf. F. and Kao, C. A. 23, 2424. Et α,α’-dibromopimelate and KCN in absolute EtOH, refluxed for 60 hrs., give 80-8% of Et 1-cyano-1,2-cyclopentanedicarboxylate, b2 126-8°, d420 1.108, nD20 1.4560; hydrolysis with concentrated HCl gives a mixture of trans- and cis-1,2-cyclopentanedicarboxylic acid (Perkins, J. Chem. Soc. 65, 572(1894)). Similarly Et α,α’-dibromosuberate yields 48-55% of Et 1-cyano-1,2-cyclohexanedicarboxylate, b2 129-30°, d420 1.082, nD20 1.4570; hydrolysis with 20% HCl yields a mixture of the 2 1,2-cyclohexanedicarboxylic acids, the trans-isomer being obtained pure (Baeyer, Ann. 258, 213(1890)). Et α,α’-dibromoazelate and Et α,α’-dibromosebacate failed to give detectable quantities of the cyclic CN esters containing 7- or 8-membered rings.

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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 《Improved synthesis of cis-Δ4-tetrahydrophthalic anhydride and cis-hexahydrophthalic acid》. Authors are Jenkins, Edward F.; Costello, Edward J..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).Product Details of 610-09-3. Through the article, more information about this compound (cas:610-09-3) is conveyed.

Maleic anhydride (1 mole) in 150 ml. C6H6, cooled to 5°, 54 g. liquid (CH2:CH)2 added, and the mixture heated to 115° (within 15 min. the temperature rises to 145° and the pressure to 11 atm.) and allowed to stand overnight, gives 90% cis-Δ4-tetrahydrophthalic anhydride (I), m. 103-4°. I (30.4 g.) in 150 ml. AcOH, hydrogenated 0.5 hr. over 200 mg. Pt oxide at room temperature and 4.5 atm., and the mixture boiled with H2O, gives 90% cis-hexahydrophthalic acid, m. 190-1°.

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Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic.Asano, Takehiro; Nakagawa, Yoshinao; Tamura, Masazumi; Tomishige, Keiichi researched the compound: Methyl tetrahydrofuran-2-carboxylate( cas:37443-42-8 ).Computed Properties of C6H10O3.They published the article 《Hydrogenolysis of tetrahydrofuran-2-carboxylic acid over tungsten-modified rhodium catalyst》 about this compound( cas:37443-42-8 ) in Applied Catalysis, A: General. Keywords: rhodium tungsten oxide silica catalyst THF carboxylic acid hydrogenolysis; hydroxyvalerate derivative hydrogenolysis catalyst. We’ll tell you more about this compound (cas:37443-42-8).

Catalysts for reduction of tetrahydrofuran-2-carboxylic acid (THFCA), which can be synthesized from furfural via oxidation and hydrogenation, were explored among the combinations of noble metal and reducible metal oxide supported on SiO2. Rh-WOx/SiO2 catalysts showed activity in C-O hydrogenolysis at 2-position of THFCA (to δ-valerolactone and 5-hydroxyvaleric acid) and higher yield ratio of these C-O hydrogenolysis products to carboxylic acid hydrogenation products than other bimetallic catalysts. The activity of Rh-WOx/SiO2 catalysts was highest at W/Rh = 0.25 mol/mol. X-ray diffraction, TPR, CO adsorption and XAFS characterizations showed that the Rh-WOx/SiO2 (W/Rh = 0.25) catalyst contained Rh metal particles with surface modification with isolated W2+ oxide species. The mechanism that hydride-like species formed on Rh atom attacks the C atom at the α-position (2-position) of adsorbed carboxylate on W atom is proposed based on the similar kinetics and similar catalyst structure to Rh-MOx/SiO2 (M = Re, Mo) which is known to be active in THFA hydrogenolysis to 1,5-pentanediol.

Compound(37443-42-8)Computed Properties of C6H10O3 received a lot of attention, and I have introduced some compounds in other articles, similar to this compound(Methyl tetrahydrofuran-2-carboxylate), if you are interested, you can check out my other related articles.

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

SDS of cas: 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 A new fluorescent chemosensor for Al(III) detection with highly selective in aqueous solution and solid test paper. Author is Xiu, Deping; Shi, Junjie; Deng, Miaoran; Song, Huihua; Hao, Zhiqiang; Feng, Qi; Yu, Haitao.

A new fluorescent chemosensor (I) based on salicylaldehyde hydrazide was facilely synthesized through one-step reaction, which exhibited turn-on fluorescent response to Al(III) with 18-fold fluorescence enhancement in aqueous solution at pH 5.5. The binding stoichiometry of 1 toward Al(III) was in 1:1. High selectivity and sensitivity to Al(III) were achieved, which featured a detection limit of 67 nmol L-1 and a linear rang of 1-10 μmol L-1. More importantly, the sensing process could be also performed on solid test paper. After the addition of Al(III), a significant emission color change from yellow to cyan was observed by naked eye due to the intrinsic aggregation-induced emission (AIE) characteristic of 1.

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Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

Related Products of 37443-42-8. 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: Methyl tetrahydrofuran-2-carboxylate, is researched, Molecular C6H10O3, CAS is 37443-42-8, about Electrochemical fluorination of several esters derived from oxolane-2-yl-carboxylic acid, oxolane-2-yl-methanol and oxane-2-yl-methanol. Author is Abe, Takashi; Tamura, Masanori; Sekiya, Akira.

Electrochem. fluorination (ECF) of ester derivatives of (tetrahydro-2-furanyl)carboxylic acid (I), (tetrahydro-2-furanyl)methanol (II) and (2-oxanyl)methanol (III) were investigated. Perfluoro oxolane carbonyl fluoride was obtained from derivatives of I and II, and perfluoro(oxane-2-yl-carbonyl fluoride) was obtained from derivatives of III as the desired compounds, resp. From the ECF of acetates, perfluoro-spiro-ether derivatives having a dioxolane ring were also obtained as the cyclization product in low yield together with a perfluoro acid fluoride. The structure of these perfluoro-spiro-ether derivatives was confirmed by analyzing the chlorinated products, which were obtained by the reaction with AlCl3.

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

Epoxy compounds usually have stronger nucleophilic ability, because the alkyl group on the oxygen atom makes the bond angle smaller, which makes the lone pair of electrons react more dissimilarly with the electron-deficient system. Compound: 2-Furoic hydrazide, is researched, Molecular C5H6N2O2, CAS is 3326-71-4, about Chemistry of mixed-ligand oxidovanadium(IV) complexes of aroylhydrazones incorporating quinoline derivatives: Study of solution behavior, theoretical evaluation and protein/DNA interaction.Safety of 2-Furoic hydrazide.

A series of eight hexacoordinated mixed-ligand oxidovanadium(IV) complexes [VO(Lx)(LN-N)] (1-8), where Lx = L1 – L4 are four differently substituted ONO donor aroylhydrazone ligands and LN-N are N,N-donor bases like 2,2′-bipyridine (bipy) (1, 3, 5 and 7) and 1,10-phenanthroline (phen) (2, 4, 6 and 8), are reported. All synthesized complexes were characterized by various physicochem. techniques and mol. structures of 1 and 6 were determined by x-ray crystallog. With a view to evaluate the biol. activity of the VIVO species, the behavior of the systems VIVO2+/Lx, VIVO2+/Lx/bipy and VIVO2+/Lx/phen was studied as a function of pH in a mixture of H2O/DMSO 50/50 (volume/volume). DFT calculations allowed finding out the relative stability of the tautomeric forms of the ligands, and predicting the structure of vanadium complexes and their EPR parameters. To study their interaction with proteins, firstly the ternary systems VIVO2+/L1,2 with 1-methylimidazole, which is a good model for histidine binding, were examined Subsequently the interaction of the complexes with lysozyme (Lyz), cytochrome c (Cyt) and bovine serum albumin (BSA) was studied. The complexes showed moderate binding affinity towards BSA, while no interaction takes place with lysozyme and cytochrome c. This could be explained with the higher number of accessible coordinating and polar residues for BSA than for Lyz and Cyt. Further, the complexes were also evaluated for their DNA binding propensity through UV-visible absorption titration and fluorescence spectral studies. These results were consistent with BSA binding affinity and showed moderate binding affinity towards CT-DNA.

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Reference:
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 Direct Catalytic Symmetrical, Unsymmetrical N,N-Dialkylation and Cyclization of Acylhydrazides Using Alcohols, published in 2020-08-21, which mentions a compound: 3326-71-4, Name is 2-Furoic hydrazide, Molecular C5H6N2O2, Synthetic Route of C5H6N2O2.

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