Heterocyclic Building Blocks-Benzisoxazole

Royes, Jordi; Ni, Shaofei; Farre, Albert; La Cascia, Enrico; Carbo, Jorge J.; Cuenca, Ana B.; Maseras, Feliu; Fernandez, Elena published an article about the compound: Methyl tetrahydrofuran-2-carboxylate( cas:37443-42-8,SMILESS:O=C(C1OCCC1)OC ).Name: Methyl tetrahydrofuran-2-carboxylate. 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:37443-42-8) through the article.

The synthesis of spiroheterocyclic structures with a pendant methylene boronate substituent has been accomplished to promote further functionalization. A Cu-catalyzed borylative ring closing C-C coupling of an alkenyl halide is the key step toward the synthesis of [m.n]-spirocycles (m,n = 3-5). Computational studies on the mechanism reproduced all the exptl. trends and explain the enhanced reactivity of systems leading to strained smaller rings. The optimized protocol also gives access to dispirocycle scaffolds, fully characterized by x-ray diffraction.

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Benzisoxazole – Wikipedia,
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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.Safety of 2-Furoic hydrazide.Prabakaran, G.; Manivarman, S.; Bharanidharan, M. published the article 《Catalytic synthesis, ADMET, QSAR and molecular modeling studies of novel chalcone derivatives as highly potent antioxidant agents》 about this compound( cas:3326-71-4 ) in Materials Today: Proceedings. Keywords: chalcone derivative antioxidant agent. Let’s learn more about this compound (cas:3326-71-4).

A series of (E)-3-(3-(5-chlorothiophen-2-yl)-1-(furan-2-carbonyl)-2,3-dihydro-1H-pyrazol-4-yl)-1-(substituted)prop-2-en-1-one derivatives 5a-c was synthesized from the reaction of 3-(5-chlorothiophen-2-yl)-1-(furan-2-carbonyl)-2,3-dihydro-1H-pyrazole-4-carbaldehyde (2) with various substituted acetophenes by the use of TiO2-ZnS in ethanol under reflux conditions. All are structurally supported by IR spectrum and the basic testing and screening, and find that compounds 5a are potential antioxidants for their in vitro-antioxidant activity against DPPH. The results in vitro were compared with the results of the mol. docking, ADMET, QSAR and bioactivity study and it was found that the results were observed in good correlations with in vitro anti-oxidant results in silicon binding affinities. The anal. of mol. dockings revealed the interactions between the synthesized ligands and protein tyrosine kinase (2HCK) amino acid residues and has a strong hydrogen connexion to this enzyme.

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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 《Hunsdiecker reaction of silver salts of cis- and trans-1,2-cyclohexanedicarboxylic acid》. Authors are Abell, Paul I..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).Application of 610-09-3. Through the article, more information about this compound (cas:610-09-3) is conveyed.

Decarboxylation of the Ag salts of cis- and trans-1,2-cyclohexanedicarboxylic acids (I, Ia) by the action of halogen according to Hunsdiecker, et al. (C.A. 38, 374), gave only trans-1,2-dibromocyclohexane (IIa) through isomerization which appeared to take place at an intermediate stage in the reaction. Com. cis-1,2-cyclohexanedicarboxylic anhydride hydrolyzed in boiling H2O gave I, m. 191-4°, isomerized by heating 8 hrs. at 170-80° with a small amount of dilute HCl in a sealed tube to yield 61.5% Ia, m. 228.5-30.5° (from EtOH). Carefully neutralized solutions of the Na salts of I and Ia treated with an exactly equivalent quantity of aqueous AgNO3 and filtered, the precipitate carefully washed with H2O, alc., and Et2O, dried several days over P2O5 in vacuo, and screened to 100 mesh gave Ag salts (III, IIIa) suitable for reaction with Br. Reaction of III and IIIa with Br was carried out at various temperatures by the inverse addition procedure of Conly (C.A. 48, 2561b) in which the dry III or IIIa was added to Br in CCl4, in an apparatus in which the speed and extent of the reaction were followed by observation of the CO2 evolved. The products of the reaction were tabulated (Ag salt, temperature of reaction, % yield, m.p. IIa, n25D, and structure as shown by infrared spectrum given): III, 0-25°, 43, -4.8°, 1.5503, all trans; III, reflux, 47, -4.7°, 1.5505, all trans; IIIa, 0-25°, 48, -4.5°, 1.5507, all trans; IIIa, reflux, 37, -2.5°, 1.5510, all trans. To establish the stability to isomerization under the above exptl. conditions, known cis-1,2-dibromocyclohexane (II) and IIa were refluxed 12 hrs. with Br and AgBr. II, m. 10.0°, n25D 1.5512, was recovered with a 60% yield of material, m. 6.5°, n25D 1.5511, all cis; and IIa, m. -4.5°, n25D 1.5505, similarly yielded 94% material, m. -4.5°, n25D 1.5505, all trans. Although the data did not distinguish partial isomerization from complete retention of configuration a very large proportion of II survived the reaction. No isomerization of II took place on 12 hrs. refluxing with Br and AgBr in anhydrous CCl4. The mechanistic implications were discussed briefly.

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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, Journal of Organic Chemistry called Hunsdiecker reaction of silver salts of cis- and trans-1,2-cyclohexanedicarboxylic acid, Author is Abell, Paul I., which mentions a compound: 610-09-3, SMILESS is O=C([C@H]1[C@@H](C(O)=O)CCCC1)O, Molecular C8H12O4, Electric Literature of C8H12O4.

Decarboxylation of the Ag salts of cis- and trans-1,2-cyclohexanedicarboxylic acids (I, Ia) by the action of halogen according to Hunsdiecker, et al. (C.A. 38, 374), gave only trans-1,2-dibromocyclohexane (IIa) through isomerization which appeared to take place at an intermediate stage in the reaction. Com. cis-1,2-cyclohexanedicarboxylic anhydride hydrolyzed in boiling H2O gave I, m. 191-4°, isomerized by heating 8 hrs. at 170-80° with a small amount of dilute HCl in a sealed tube to yield 61.5% Ia, m. 228.5-30.5° (from EtOH). Carefully neutralized solutions of the Na salts of I and Ia treated with an exactly equivalent quantity of aqueous AgNO3 and filtered, the precipitate carefully washed with H2O, alc., and Et2O, dried several days over P2O5 in vacuo, and screened to 100 mesh gave Ag salts (III, IIIa) suitable for reaction with Br. Reaction of III and IIIa with Br was carried out at various temperatures by the inverse addition procedure of Conly (C.A. 48, 2561b) in which the dry III or IIIa was added to Br in CCl4, in an apparatus in which the speed and extent of the reaction were followed by observation of the CO2 evolved. The products of the reaction were tabulated (Ag salt, temperature of reaction, % yield, m.p. IIa, n25D, and structure as shown by infrared spectrum given): III, 0-25°, 43, -4.8°, 1.5503, all trans; III, reflux, 47, -4.7°, 1.5505, all trans; IIIa, 0-25°, 48, -4.5°, 1.5507, all trans; IIIa, reflux, 37, -2.5°, 1.5510, all trans. To establish the stability to isomerization under the above exptl. conditions, known cis-1,2-dibromocyclohexane (II) and IIa were refluxed 12 hrs. with Br and AgBr. II, m. 10.0°, n25D 1.5512, was recovered with a 60% yield of material, m. 6.5°, n25D 1.5511, all cis; and IIa, m. -4.5°, n25D 1.5505, similarly yielded 94% material, m. -4.5°, n25D 1.5505, all trans. Although the data did not distinguish partial isomerization from complete retention of configuration a very large proportion of II survived the reaction. No isomerization of II took place on 12 hrs. refluxing with Br and AgBr in anhydrous CCl4. The mechanistic implications were discussed briefly.

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Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: Methyl tetrahydrofuran-2-carboxylate, is researched, Molecular C6H10O3, CAS is 37443-42-8, about A Powerful Chiral Phosphoric Acid Catalyst for Enantioselective Mukaiyama-Mannich Reactions, the main research direction is imine ketene acetal chiral phosphoric acid enantioselective Mukaiyama Mannich; amino carboxylic ester stereoselective preparation quaternary stereogenic center; chiral phosphoric acid preparation enantioselective diastereoselective Mukaiyama Mannich catalyst; Brønsted acids; Mukaiyama-Mannich reactions; asymmetric catalysis; chiral phosphoric acids; quaternary stereogenic centers.Category: benzisoxazole.

A new BINOL-derived chiral phosphoric acid bearing 2,4,6-trimethyl-3,5-dinitrophenyl substituents at the 3,3′-positions was developed. The utility of this chiral phosphoric acid is demonstrated by a highly enantioselective (ee up to >99 %) and diastereoselective (syn/anti up to >99:1) asym. Mukaiyama-Mannich reaction of imines with a wide range of ketene silyl acetals. Moreover, this method was successfully applied to the construction of vicinal tertiary and quaternary stereogenic centers with excellent diastereo- and enantioselectivity. Significantly, BINOL-derived N-triflyl phosphoramide constitutes a complementary catalyst system that allows the title reaction to be applied to more challenging imines without an N-(2-hydroxyphenyl) moiety.

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Benzisoxazole – Wikipedia,
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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, Antifungal Activity, 3D-QSAR and Molecular Docking Study of Novel Menthol-Derived 1,2,4-Triazole-thioether Compounds, published in 2021, which mentions a compound: 3326-71-4, Name is 2-Furoic hydrazide, Molecular C5H6N2O2, Quality Control of 2-Furoic hydrazide.

A series of novel menthol-derived triazole-thioether compounds I [R = 2-MeC6H4, 3,4-di-MeOC6H3, 2-thienyl, etc.] were designed, synthesized, characterized structurally and evaluated biol. to explore more potent natural product-based antifungal agents. The bioassay results revealed that at 50μg/mL, some of the target compounds exhibited good inhibitory activity against the tested fungi, especially against Physalospora piricola. Compounds I [R = 2-MeC6H4, 2-ClC6H4, 3,4-di-MeOC6H3, 2-furyl, etc.] had inhibition rates of 93.3%, 79.4%, and 79.4%, resp., against P. piricola, much better than that of the pos. control chlorothalonil. Compounds I [R = 3,4-di-MeOC6H3, 3-FC6H4] held inhibition rates of 82.4% and 86.5% against Cercospora arachidicola and Gibberella zeae, resp., much better than that of the com. fungicide chlorothalonil. Compound I [R = 2-MeC6H4] displayed antifungal activity of 90.5% and 83.8%, resp., against Colleterichum orbicalare and Fusarium oxysporum f. sp. cucumerinum. Compound I [R = 2-IC6H4] had inhibition rates of 88.6%, 80.0%, and 88.0%, resp., against F. oxysporum f. sp. cucumerinu, Bipolaris maydis and C. orbiculare. Furthermore, compound I [R = 2-MeC6H4] showed the best and broad-spectrum antifungal activity against all the tested fungi. To design more effective antifungal compounds against P. piricola, 3D-QSAR anal. was performed using the CoMFA method, and a reasonable 3D-QSAR model (r2 = 0.991, q2 = 0.514) was established. The simulative binding pattern of the target compounds with cytochrome P 450 14α-sterol demethylase (CYP51) was investigated by mol. docking.

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Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

Beyzaei, Hamid; Malekraisi, Farideh; Aryan, Reza; Ghasemi, Behzad published the article 《Green aqueous synthesis and antimicrobial evaluation of 3,5-disubstituted 1,2,4-triazoles》. Keywords: disubstituted triazole green preparation antibacterial antifungal.They researched the compound: 2-Furoic hydrazide( cas:3326-71-4 ).SDS of cas: 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.

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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Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

Most of the natural products isolated at present are heterocyclic compounds, so heterocyclic compounds occupy an important position in the research of organic chemistry. A compound: 3326-71-4, is researched, SMILESS is O=C(C1=CC=CO1)NN, Molecular C5H6N2O2Journal, Russian Journal of Organic Chemistry called Modification of Monocarboxylic Acid Hydrazides with Tropylium Salts, Author is Yunnikova, L. P.; Esenbaeva, V. V., the main research direction is hydrazide tropylium salt modification.Product Details of 3326-71-4.

Nicotinic, isonicotinic, and furan-2-carboxylic acid hydrazides reacted with 2 equiv of tropylium perchlorate or tetrafluoroborate to give the corresponding N’N’-di(cyclohepta-2,4,6-trein-1-yl) derivatives as a result of electrophilic substitution of both hydrogen atoms in the primary amino group. The reaction of furan-2-carbohydrazide with an equimolar amount of tropylium salt gave N’-(cyclohepta-2,4,6-trien-1-yl)furan-2-carbohydrazide.

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Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

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 Synthesis, crystal structure, DNA/bovine serum albumin binding and antitumor activity of two transition metal complexes with 4-acylpyrazolone derivative. Author is Zhang, Yan-Ping; Li, Yue; Xu, Guan-Cheng; Li, Jin-Yu; Luo, Hua-Ying; Li, Jin-Yao; Zhang, Li; Jia, Dian-Zeng.

Two new complexes, namely [Cu6L6] (1) and [Zn(HL)2] (2) (H2L = N-(1-phenyl-3-methyl-4-propenylidene-5-pyrazolone)-2-furancarboxylic acid hydrazide), have been synthesized and characterized. Single crystal x-ray anal. indicates that complex 1 has a hexanuclear structure and complex 2 exhibits a mononuclear structure. The DNA/bovine serum albumin (BSA) binding properties of 1 and 2 were investigated by absorption spectroscopy and fluorescence quenching. Both complexes could effectively intercalate to DNA with calculated quenching constants of 2.6 × 105 and 1.25 × 105 M-1, resp. The quenching mechanism of the intrinsic fluorescence of BSA by the complexes is a static one. The cytotoxicities of 1 and 2 were investigated in two human tumor cell lines, human esophageal cancer cells (Eca-109) and cervical cancer cells (HeLa). Complex 1 exhibits higher antitumor activity than 2. Furthermore, 1 can inhibit HeLa cells by inducing apoptosis and G0/G1 phase cell cycle arrest. All results demonstrate that 1 and 2 both have DNA/BSA binding capacity and antitumor activity.

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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 《Stereochemistry of cyclic compounds. 1,3-Cyclopentenedione in Diels-Alder reaction》. Authors are Kucherov, V. F.; Ivanova, L. I..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).Recommanded Product: 610-09-3. Through the article, more information about this compound (cas:610-09-3) is conveyed.

Oxidation of 1,3-cyclopentenediol with CrO3 in AcOH with ice cooling gave 26% 1,3-cyclopentenedione (I), b1 60°, n20D 1.5045, m. 35-6°, after cooling. The dione condenses readily with butadiene in C6H6 (pyrogallol added) in 2 weeks at room temperature to yield cis-Δ5-hexahydroindene-1,3-dione, m. 157.5-8.5°; hydrogenation over Pd gave 1,3-hydrindandione, m. 86-6.5°, which with Br2-NaOH gave cis-1,2-cyclohexanedicarboxylic acid, m. 186.5-7.5°. I condensed with isoprene in C6H6 to the adduct, 5-methyl-Δ5-hexahydroindene-1,3-dione, m. 84.5-5.5°. Cyclopentadiene gave the adduct, C10H10O2, m. 178-8.5°, which hydrogenated over Pd to endomethylenehydrindan-1,3-dione, m. 166-6.5°. I and 1-vinylcyclohexene gave the adduct, 4,5-tetramethylene-Δ5-hexahydroindene-1,3-dione, m. 120-1°. I and 6-methoxy-1-vinyl-Δ3,4-dihydronaphthalene similarly gave in 1 day at room temperature II, m. 206.5-7.5°.

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