Heterocyclic Building Blocks-Benzisoxazole

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, Jingxi Huagong called Synthesis of the alkyl esters of α-furoic acid as flavors, Author is Yao, Lihong; Su, Chang’an; Chen, Xin; Qi, Liquan; Tie, Mei, which mentions a compound: 37443-42-8, SMILESS is O=C(C1OCCC1)OC, Molecular C6H10O3, Application In Synthesis of Methyl tetrahydrofuran-2-carboxylate.

The seven alkyl esters of α-furoic acid were synthesized in 80-95.6% yields by refluxing the solution of benzene (or toluene) containing 0.1 mol α-furoic acid and the corresponding aliphatic alcs. (0.12∼0.5 mol) for 3 h in the presence of p-toluenesulfonic acid (0.01 mol) and 5 mL 30% hydrogen peroxide.

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

HPLC of Formula: 3326-71-4. 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 4,6-Diacetyl Resorcinol Based Vanadium(V) Complexes: Reactivity and Catalytic Applications. Author is Maurya, Mannar R.; Jangra, Nancy; Avecilla, Fernando; Correia, Isabel.

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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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 《FT-IR and FT-Raman spectroscopy study of the cyclic anhydride intermediates for the esterification of cellulose. Part 3. Cyclic anhydrides formed by the isomers of cyclohexanedicarboxylic acid》. Authors are Yang, Charles Q.; Zhang, Guobao.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 In Synthesis of cis-Cyclohexane-1,2-dicarboxylic acid. Through the article, more information about this compound (cas:610-09-3) is conveyed.

Multifunctional carboxylic acids were used as crosslinking agents for cotton and wood pulp cellulose. In the authors’ previous research, the authors found that a polycarboxylic acid esterifies cellulose through the formation of a 5-membered cyclic anhydride intermediate by the dehydration of 2 carboxyl groups. The authors studied the formation of those cyclic anhydride intermediates by different isomers of cyclohexanedicarboxylic acid (CHA) so that the authors can elucidate the effects of mol. structure on the formation of the anhydride intermediates. The authors found that both cis- and trans-1,2-CHA form 5-membered anhydride intermediates when temperature reaches their m.p. and that cis-1,2-CHA forms the cyclic anhydride at temperatures lower than does trans-1,2-CHA. 1,3-CHA forms 6-membered cyclic anhydride at temperatures much higher than its m.p. The formation of a 5-membered cyclic anhydride intermediates takes place at temperatures lower than that of a 6-membered anhydride. This is probably the main reason why those polycarboxylic acids with their carboxylic acid groups bonded to the adjacent carbons of the mol. backbones are more effective crosslinking agents for cellulose than those with their carboxylic groups bonded to the alternative carbons. No formation of cyclic anhydride was found for 1,4-CHA. The formation of a 5-membered cyclic anhydride was accelerated by monosodium phosphate, which is used as a catalyst for the esterification of cotton cellulose by polycarboxylic acids.

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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: 37443-42-8, is researched, SMILESS is O=C(C1OCCC1)OC, Molecular C6H10O3Journal, Tsuruoka Kogyo Koto Senmon Gakko Kenkyu Kiyo called Catalytic hydrogenation of furan derivatives. 8. The behavior of products with the passage of the reaction time, Author is Shinozaki, Kohichi; Abe, Mitsuyuki; Uchiyama, Midori, the main research direction is hydrogenation furan palladium; THF preparation catalyst.Quality Control of Methyl tetrahydrofuran-2-carboxylate.

Hydrogenation of I in R1OH (R1 = lower alkyl) in the presence of Pd black or PdO was studied. I (R = H, Me) over Pd black formed small amounts of intermediate by-product ketals (II), which were hydrogenolyzed to the main products (III). With PdO, considerable amounts of II were formed from I (R = H, Me, CH:CHCO2Me, CO2Me). The amount of II formed decreased with increasing size of both R and R1.

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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 Michael addition mediated domino cyclization of hydrazide embedded pyrazolyl derivatives: biological and its molecular docking examinations, published in 2021, which mentions a compound: 3326-71-4, mainly applied to quinoline pyrazoline preparation antitumor antibacterial human mol docking, Electric Literature of C5H6N2O2.

Three quinolinyl-tethered pyrazolines I (R = 3-MeOC6H4, 2-furyl, 4-pyridyl) were synthesized in good yields by domino Michael-addition/cyclization of (E)-2-chloro-3-[2-(4-methylphenyl)ethenyl]-8-methylquinoline, prepared from 2-chloro-8-methyl-3-quinolinecarboxaldehyde and 4-methylacetophenone, with arylhydrazides RC(O)NHNH2. The newly synthesized compounds have been examined for the antimicrobial and anticancer activities by MTT assay as well as mol. docking studies.

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Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics

Name: Methyl tetrahydrofuran-2-carboxylate. 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: Methyl tetrahydrofuran-2-carboxylate, is researched, Molecular C6H10O3, CAS is 37443-42-8, about Palladium-catalyzed asymmetric hydrogenation of furan carboxylic acids. Author is Maris, Mihaela; Huck, Wolf-Rudiger; Mallat, Tamas; Baiker, Alfons.

Enantioselective hydrogenation of aromatic and heteroaromatic compounds is the field where chirally modified metal hydrogenation catalysts have the biggest potential compared to homogeneous chiral transition metal complexes. Here we report the hydrogenation of furan and benzofuran carboxylic acids over a cinchonidine-modified 5 wt% Pd/Al2O3 catalyst. (S)-Tetrahydrofuran-2-carboxylic acid was synthesized in 4 h at rt and 30 bar with 95% yield and 32% ee. The ee was lower in the hydrogenation of methylfuran carboxylic acids but up to 100% de was achieved. In the slow hydrogenation of benzofuran-2-carboxylic acid, the ee went up to 50% at 29% yield. The potential application of the method is limited by the competing hydrogenation of the quinoline rings of cinchonidine in the latter reaction, necessitating the feeding of small amounts of cinchonidine during reaction. Still, this simple method using an easily available chiral modifier and catalyst affords the highest rate and ee reported so far in the catalytic asym. hydrogenation of furan and benzofuran carboxylic acids, and it may be an attractive route in combination with optical resolution We assume that the reaction mechanism is analogous to that described for α,β-unsaturated carboxylic acids over the same catalyst, involving a 1:2-type interaction between the cinchonidine and the acid dimer.

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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 Preparation of γ-butyrolactones by the oxidation of monofunctional derivatives of tetrahydrofuran, published in 1972, which mentions a compound: 37443-42-8, Name is Methyl tetrahydrofuran-2-carboxylate, Molecular C6H10O3, Name: Methyl tetrahydrofuran-2-carboxylate.

Liquid phase oxidation of tetrahydrofurfuryl alc., its formate and acetate, and Me 2-tetrahydrofurancarboxylate, largely at 115°, in 10-25 hr in a flow-type glass reactor gave good yields of γ-butyrolactone or its γ-CH2OH, CH2O2CH, CH2OAc or CO2Me derivatives, resp., HCO2H and succinic acid. Evidently the oxidation occurred at the C2 and C5 positions. Uv light promoted the reaction and allowed its operation at lower temperature The summary yields of the lactones were 72-95%. The last substrate above was oxidized in the presence of Mn(OAc)2.4H2O catalyst at 70°.

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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: 37443-42-8, is researched, SMILESS is O=C(C1OCCC1)OC, Molecular C6H10O3Journal, ACS Catalysis called Copper-Catalyzed Borylative Ring Closing C-C Coupling toward Spiro- and Dispiroheterocycles, Author is Royes, Jordi; Ni, Shaofei; Farre, Albert; La Cascia, Enrico; Carbo, Jorge J.; Cuenca, Ana B.; Maseras, Feliu; Fernandez, Elena, the main research direction is copper catalyst borylative ring closing coupling spiro dispiroheterocycle mechanism; crystal structure mol spiroheterocyclic pendant methylene boronate preparation optimized.Category: benzisoxazole.

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,
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.Morawetz, Herbert; Choi, Ling Siu researched the compound: cis-Cyclohexane-1,2-dicarboxylic acid( cas:610-09-3 ).Quality Control of cis-Cyclohexane-1,2-dicarboxylic acid.They published the article 《Ionization equilibria in dicarboxylic acids undergoing conformational transitions》 about this compound( cas:610-09-3 ) in Journal of Physical Chemistry. Keywords: ionization dicarboxylic acid conformation; succinic acid ionization conformation. We’ll tell you more about this compound (cas:610-09-3).

Succinic acid and substituted succinic acids undergo conformational transitions during ionization, and these are expected to affect their ionization equilibrium The 1H NMR data on the dependence of the conformational equilibrium of succinic acid and meso-2,3-dimethylsuccinic acid on their degree of ionization are interpreted in terms of the ratio of the 2nd ionization constants of the gauche and trans isomer, K2g/K2t, and the equilibrium constant Kc for the gauche-trans transition of the unionized acid. The K2g/K2t ratios obtained for the 2 above acids are compared with theratio of the 2nd ionization constants of cis- and trans-cyclohexane-1,2-dicarboxylic acids used as model compounds in which the carboxyls are gauche and trans to each other.

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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 《Hydrogenation of aromatic compounds with the aid of platinum. III. Hydrogenation with platinum containing oxygen》. Authors are Willstatter, Richard; Jaquet, Daniel.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.

cf. C. A. 7, 1508. Certain reductions, like that of phthalic anhydride (a), which cannot be effected catalytically with Pt free from O, can be initiated by loading the Pt with O and brought to completion by again treating the Pt with O as the catalyst gradually loses its O by the formation of H2O. Oxygen-free Pt and that containing O behave like 2 different contact substances in reduction processes. Thus, 20.3 g. (a) in 75 cc. glacial AcOH with 5 g. Pt absorbed only 400 cc. H; if, however, the H gasometer was shut off and the reaction bulb evacuated, then allowed to fill with air, shaken 1 min. (whereupon O was rapidly absorbed -about 5 cc. per g. Pt) and the air was driven out with H, about 500 cc. of H was again absorbed after each such activation until the 20th and 21st times, when the absorption of H was 1230 and 5600 cc., rasp. The total absorption was 17040 cc. (20°, 760 mm.) or, deducting about 1150 cc. used up by the O introduced in the activations, 15890 cc. or 4.8 mols. Of the 2 rings in (a) the 5-membered one is reduced before the C6H6 ring; the first product is phthalide (b) which is partially reduced to hexahydrophthalide (c) and partially to o-MeC6H4CO2H (d) which is then reduced to the hexahydrotoluic acid (e). If the process is interrupted when only a little H has been absorbed there is obtained, besides some C6H6(CO2H)2, a mixture of (b) and (c), and while (b) is easily reduced further to (d), (c) cannot be reduced to (e). If in the process of isolation alkali is employed the (c) is in part obtained as methylolhexahydrobenzoic acid. Among the reduction products is also cis-hexahydrophthalic acid (f). In the reduction described above were obtained 7 g. (c) (partially hydrolyzed), 7 g. (e) and 4 g. (f). In a similar reduction of (b) 3.4 mols. H were absorbed and there were obtained about equal parts of (e) and (c). Phthalimide behaves quite differently from (a) on reduction, the aromatic nucleus and not the CO groups taking up the O. The activation of the Pt with O is not necessary but the reduction is successful only with the best Pt sponge preparations; many which were active towards C6H6 were inactive towards the imide. Nor can MeOH, EtOH or cyclohexane be used as a solvent; in glacial AcOH the reduction proceeds smoothly. cis-Hexahydrophthalimide seps. from H2O, alc. and AcOH in monoclinic prisms, m. 132°. Naphthalic acid purified by crystallization from alc. cannot be reduced because it always contains some anhydride (g) but the acid freshly precipitated from alk. solution can be reduced; contrary to C10H8, it takes up only 4 atoms of H; the tetrahydronaphthalic acid (h) seps. in cube-like prisms, m. 196° with loss of H2O and conversion into the anhydride, m. 119°. (g), like (a), can be reduced only with Pt activated with O; after about 4 mols. H2 have been absorbed the reaction slows up. As far as the (g) itself is reduced, the anhydride ring is attacked, but as some of the (g) is hydrolyzed by the H2O formed, some (h) is obtained. Among the reduction products are tetrahydro-1-methylnaphthalene-8-carboxylic acid (i), tetra- and decahydronaphthalides and a small amount of decahydroacenaphthene. The 2 naphthalides could not be isolated pure. The (i) seps. from Et2O-petr. ether in needles, m. 150°. o-C6H4(CO2H)2 is easily reduced in AcOH when entirely free from the anhydride, yielding exclusively the cis-hexahydro acid, m. 191-2°. The p-acid in AcOH suspension is reduced much more rapidly on gentle warming, giving about equal parts of the cis- and cis-trans-hexahydro acids, m. 162-3° and about 300°, resp. The m-acid, if pure, is likewise easily reduced in AcOH suspension, forming chiefly the cis- and some cis-trans-hexahydro acid. p-Toluylic acid very quickly gives exclusively or almost exclusively the liquid hexahydro acid whose amide m. 175-6°. Indole in AcOH smoothly absorbs 8 atoms H with formation of perhydroindole, b720 182-3°, b12 65°, a basic oil of medium consistency and unpleasant, penetrating, onion-like odor, d420 0.9947; chloroplatinate, reddish yellow monoclinic tablets from alc., m. 172-3° (not sharply); picrate, fine needles from alc., m. 137-8° (not sharply). If the reduction is interrupted before it is complete (e. g., when 2 atoms of H have been absorbed), the product contains unchanged indole, dihydroindole and perhydroindole, the last being removed by shaking the Et2O solution with 0.1 N HCl until the alk. reaction just disappears, and the first two being separated by fractional precipitation from Et2O with picric acid.

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