Day: April 20, 2022

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.Qian, Peng; Zhou, Zhenghong; Wang, Li; Wang, Zhicheng; Wang, Zhongwei; Zhang, Zhenlei; Sheng, Liangquan researched the compound: 2-Furoic hydrazide( cas:3326-71-4 ).SDS of cas: 3326-71-4.They published the article 《Electrosynthesis of 2-(1,3,4-Oxadiazol-2-yl)aniline Derivatives with Isatins as Amino-Attached C1 Sources》 about this compound( cas:3326-71-4 ) in Journal of Organic Chemistry. Keywords: oxadiazolyl aniline electrosynthesis intramol decarboxylative coupling isatin hydrazine. We’ll tell you more about this compound (cas:3326-71-4).

An intramol. decarboxylative coupling reaction for the construction of 2-(1,3,4-oxadiazol-2-yl)aniline derivatives was developed from readily available isatins and hydrazides by virtue of electrochem. In this reaction, isatins were employed as amino-attached C1 sources, providing a variety of 2-(1,3,4-oxadiazol-2-yl)aniline derivatives with moderate to good yields.

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Reference:
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: 2-Furoic hydrazide(SMILESS: O=C(C1=CC=CO1)NN,cas:3326-71-4) is researched.Electric Literature of C12H12N2. The article 《Tin powder promoted synthesis of α-trifluoromethyl homoallylic hydrazides》 in relation to this compound, is published in Youji Huaxue. Let’s take a look at the latest research on this compound (cas:3326-71-4).

An efficient tin powder promoted multicomponent one-pot reaction was developed for the synthesis of α-trifluoromethyl homoallylic hydrazides from Et trifluoropyruvate, hydrazides and allylic bromides in the presence of Bronsted and Lewis acid in 1,4-dioxane under reflux conditions. The method avoids the use of toxic stannanes and allows easy operation. The reaction proceeds smoothly under mild reaction conditions to give the corresponding products in good yields.

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

Li, Zhe-qi; Wu, Yan-bo; Cao, Kui published the article 《Technology of selective hydrogenation and methyl esterification of furoic acid over Pd/γ-Al2O3 catalyst》. Keywords: selective hydrogenation methyl esterification furoic acid platinum gamma alumina.They researched the compound: Methyl tetrahydrofuran-2-carboxylate( cas:37443-42-8 ).Related Products of 37443-42-8. 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:37443-42-8) here.

The hydrogenation and Me esterification of furoic acid over Pd/γ-Al2O3 catalysts were investigated in a fixed-bed microreactor by one-step method. Effects of the reaction temperature, pressure, gas flow rate of H2, liquid flow rate of furoic acid and method were studied. Under the optimal reaction conditions of 0.5 MPa pressure, at 150°, H2 gas flow rate of 5000 mL/h-1 and liquid flow rate of 5.0 mL/h-1, the conversion of furoic acid, selectivity to Me THF formiate and yield of Me THF formiate can reach 99.0%, 98.2%, and 97.2%, resp. Performance of the catalyst does not deteriorate after being used for 360 h. This green technol. has the characteristic of low reaction pressure, easy operation, high activity and selectivity and stability of the catalyst and facile separation of the catalyst from products.

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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: Methyl tetrahydrofuran-2-carboxylate( cas:37443-42-8 ) is researched.SDS of cas: 37443-42-8.Ali, Rameez; Guan, Yong; Leveille, Alexandria N.; Vaughn, Elizabeth; Parelkar, Sangram; Thompson, Paul R.; Mattson, Anita E. published the article 《Synthesis and Anticancer Activity of Structure Simplified Naturally Inspired Dimeric Chromenone Derivatives》 about this compound( cas:37443-42-8 ) in European Journal of Organic Chemistry. Keywords: dimeric chromenone synthesis anticancer; tetrahydroxanthone synthesis anticancer; Cancer; Drug Design; Drug Discovery; Medicinal Chemistry; Natural Products. Let’s learn more about this compound (cas:37443-42-8).

Select dimeric chromenones exhibit low micromolar cytotoxicity toward lymphoma and leukemia cell lines, L5178Y and HL60, resp. The bioactive dimeric chromenones were identified from a focused library of structurally simplified derivatives of naturally occurring dimeric chromenones and tetrahydroxanthones that was prepared as part of this study. The simple dimeric chromenone scaffolds contain no stereogenic centers, are easily synthesized, and may be utilized as lead compounds in cancer research and drug discovery.

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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 《Synthesis of bicyclo[4.2.0]octane-7,8-diol, a derivative of “”cycloöctatetraene dichloride””》. Authors are Cope, Arthur C.; Herrick, Elbert C..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).COA of Formula: C8H12O4. Through the article, more information about this compound (cas:610-09-3) is conveyed.

Butadiene (0.6-0.8 l./min.) was passed into 500 cc. dry warmed C6H6 containing 196 g. maleic anhydride and heating discontinued when the temperature reached 50°; the absorption of gas gradually slowed and was stopped in 2-2.5 hrs., and the mixture allowed to stand overnight, yielding 281.5-94.5 g. cis-Δ4-tetrahydrophthalic anhydride (I), m. 103-4°. I (228 g.), 525 cc. com. absolute EtOH, and 2.5 g. p-MeC6H4SO3H were refluxed 12-16 hrs., the EtOH removed by 2 azeotropic distillations with PhMe, the residue cooled, 200 cc. ether added, and the ether extract dried, yielding 280-92 g. cis-di-Et Δ1-tetrahydrophthalate (II), b5 129-31°, n23D 1.4610; the same procedure yielded 239 g. di-Me ester (III), b5 120-2°, n25D 1.4700. Hydrogenation of 226 g. II with 0.5 g. prereduced Adams catalyst in 20 cc. absolute EtOH or 1 g. 1% Pd-on-C without solvent at 30-15 lb./sq. in. for 3-5 hrs. yielded 215-19 g. cis-hexahydrophthalate (IV), b9 130-2°, n25D 1.4510; hexahydro compound from III, b5 110-12°, n25D 1.4570. In the following preparation all materials and apparatus were carefully dried; the original paper should be consulted for details. IV (76 g.) in 2130 cc. xylene was added during 45.5 hrs. to 1 l. refluxing xylene containing 31.3 g. Na, the mixture cooled in an ice-salt bath, 1.5 l. xylene siphoned off and discarded, 78.5 cc. AcOH in 500 cc. ether added during 30 min., the NaOAc filtered off and extracted with ether, and the ether and xylene distilled off in vacuo, yielding 1.1 g. bicyclo[4.2.0]octan-7-ol-8-one (VI), m. 178-84.5° (from EtOH); fractionation of the residue from the ether filtrate yielded 5.7 g. VI, n25D 1.4992, d254 1.1218, MRD calculated 36.66, found 36.71. The following derivatives of VI were prepared and purified by chromatography: 3,5-dinitrobenzoate, m. 131-2° (from methylcyclohexane); p-phenylazobenzoate, m. 138-9° (from hexane); 2,4-dinitrophenylosazone, m. 248.5-57.5° (from EtOAc); the residue yielded an uninvestigated compound, m. 152.5-3.5°. VI (1.89 g.) reduced at atm. pressure in 40 cc. absolute EtOH with 2 g. W-7 Raney Ni yielded 0.315 g. trans-bicyclo[4.2.0]octane-7,8-diol (VII), m. 140.5-1.5°. VII (0.043 g.) and 0.326 g. p-PhN2C6H4COCl (VIII) refluxed 11 hrs. with 10 cc. pyridine yielded 0.132 g. bis(p-phenylazobenzoate), m. 174.8-5.8° (from methylcyclohexane). Concentration of the hexane solution from VII and distillation of the residue yielded 5% cis-bicyclo compound (IX), m. 71.5-3.5°; VIII derivative, m. 165-6°. Addnl. evidence for the structure of IX and VII was obtained from their effect on the pH of 0.1 M boric acid.

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Reference:
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.Thuery, Pierre; Atoini, Youssef; Harrowfield, Jack researched the compound: cis-Cyclohexane-1,2-dicarboxylic acid( cas:610-09-3 ).Related Products of 610-09-3.They published the article 《Crown Ethers and Their Alkali Metal Ion Complexes as Assembler Groups in Uranyl-Organic Coordination Polymers with cis-1,3-, cis-1,2-, and trans-1,2-Cyclohexanedicarboxylates》 about this compound( cas:610-09-3 ) in Crystal Growth & Design. Keywords: uranyl alkali metal crown ether cyclohexanedicarboxylate polymeric complex preparation; crystal structure uranyl alkali metal crown ether cyclohexanedicarboxylate polymer; luminescence uranyl alkali metal crown ether cyclohexanedicarboxylate polymeric complex. We’ll tell you more about this compound (cas:610-09-3).

Alkali metal cations (Na+, K+) and crown ether mols. (12C4, 15C5, 18C6) were used as addnl. reactants during the hydrothermal synthesis of uranyl ion complexes with cis/trans-1,3-, cis-1,2- and trans-1,2-cyclohexanedicarboxylic acids (c/t-1,3-chdcH2, c-1,2-chdcH2, and t-1,2-chdcH2, resp., the latter as racemic or pure (1R,2R) enantiomer). Oxalate anions generated in situ are present in all the six complexes isolated and crystallog. characterized, [(UO2)2(c-1,3-chdc)2(C2O4)][UO2(H2O)5]·(12C4)·2H2O (1), [(UO2)4Na2(c-1,2-chdc)2(C2O4)3(15C5)2] (2), [(UO2)4K2(c-1,2-chdc)2(C2O4)3(18C6)1.5(H2O)1.5] (3), [(UO2)12K5(R-t-1,2-chdc)4(C2O4)10(18C6)5(OH)(H2O)3]·4H2O (4), [(UO2)12K5(rac-t-1,2-chdc)4(C2O4)10(18C6)5(OH)(H2O)3]·4H2O (5), and [(UO2)8K4(rac-t-1,2-chdc)4(C2O4)6(18C6)3(H2O)2] (6). In complex 1, the [UO2(H2O)5]2+ counterions link the ladderlike uranyl-containing one-dimensional polymers and the uncomplexed crown ether mols. through hydrogen bonds. In all the other complexes, two-dimensional uranyl/chdc/oxalate subunits are formed, with topologies depending on the stoichiometry, in which the 1,2-chdc2- ligands are bound to three uranium atoms, one of them chelated by the two carboxylate groups, and the oxalate ligands are bis-chelating. In complex 2, the Na(15C5)+ cations are bound to one layer through double Na-carboxylate or Na-oxo cis-bonding and they are thus mere decorating groups. In contrast, the quasi-planar K(18C6)+ groups in 3-6, partially affected by disorder, are generally trans-coordinated to two uranyl oxo groups pertaining to different layers, thus uniting the latter into a three-dimensional framework.

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

Love, Dillon; Kim, Kangmin; Domaille, Dylan W.; Williams, Olivia; Stansbury, Jeffrey; Musgrave, Charles; Bowman, Christopher published an article about the compound: 2-Furoic hydrazide( cas:3326-71-4,SMILESS:O=C(C1=CC=CO1)NN ).HPLC of Formula: 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.

Despite the powerful nature of the aza-Michael reaction for generating C-N linkages and bioactive moieties, the bis-Michael addition of 1° amines remains ineffective for the synthesis of functional, step-growth polymers due to the drastic reduction in reactivity of the resulting 2° amine mono-addition adduct. In this study, a wide range of com. hydrazides are shown to effectively undergo the bis-Michael reaction with divinyl sulfone (DVS) and 1,6-hexanediol diacrylate (HDA) under catalyst-free, thermal conditions to afford moderate to high mol. weight polymers with Mn = 3.8-34.5 kg mol-1. The hydrazide-Michael reactions exhibit two distinctive, conversion-dependent kinetic regimes that are 2nd-order overall, in contrast to the 3rd-order nature of amines previously reported. The mono-addition rate constant was found to be 37-fold greater than that of the bis-addition at 80°C for the reaction between benzhydrazide and DVS. A significant majority (12 of 15) of the hydrazide derivatives used here show excellent bis-Michael reactivity and achieve >97% conversions after 5 days. This behavior is consistent with calculations that show minimal variance of electron d. on the N-nucleophile among the derivatives studied. Reactivity differences between hydrazides and hexylamine are also explored. Overall, the difference in reactivity between hydrazides and amines is attributed to the adjacent nitrogen atom in hydrazides that acts as an efficient hydrogen-bond donor that facilitates intramol. proton-transfer following the formation of the zwitterion intermediate. This effect not only activates the Michael acceptor but also coordinates with addnl. Michael acceptors to form an intermol. reactant complex.

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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 《The kinetics of the acid-catalyzed hydrolysis of the methyl esters of cyclohexanedicarboxylic acids》. Authors are Smith, Hilton A.; Scrogham, Kenneth G.; Stump, Billy L..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).COA of Formula: C8H12O4. Through the article, more information about this compound (cas:610-09-3) is conveyed.

Isomeric cyclohexane dicarboxylic acids (I) were made by reduction of phthalic acids: cis-1,2 (II), m. 194°; trans-1,2 (III), m. 227.5-9.4°; cis-1,3 (IV), m. 167.2-8.2°; cis-1,4 (V), m. 170-2°; and trans-1,4 (VI), m. 312-13°. Di-Me esters made by acid-catalyzed esterification with MeOH were: II, b12 124.4°; III, m. 30.2-30.8°; V, b10 131°; and VI, m. 69°. IV di-Me ester, b10 130.6°, was made from the Ag salt and MeI, whereas trans-1,3-di-Me ester (VII), b20 140°, was made from H and 1,3-C6H4(CO2Me)2 with Adams Pt catalyst. Mono-Me derivative of II, m. 68.5-9.0°, was made similarly from 2-HO2CC6H4CO2Me and H. Mono-Me derivative of III, m. 94.5-95°, was made from the acid and MeOH. Mono-Me derivative of IV, m. 66.2-7.0°, was made from the acid chloride and MeOH. By treatment of the di-Me esters with 1 equivalent KOH, mono-Me derivative of V, m. 106.6-8.6°, mono-Me derivative of VI, m. 125.6-6.8°, and mono-Me derivative of trans-1,3-I were prepared Acid-catalyzed rate constants for these esters were determined at 25°, 35°, 45°, and 55° and the heats of activation calculated Me and di-Me esters of II and III hydrolyzed most slowly, those of IV and VI most rapidly, and those of V and VII at an intermediate rate.

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

Heterocyclic compounds can be divided into two categories: alicyclic heterocycles and aromatic heterocycles. Compounds whose heterocycles in the molecular skeleton cannot reflect aromaticity are called alicyclic heterocyclic compounds. Compound: 37443-42-8, is researched, Molecular C6H10O3, about A scalable chemoenzymic preparation of (R)-tetrahydrofuran-2-carboxylic acid, the main research direction is chemoenzymic asym preparation tetrahydrofurancarboxylic acid; protease asym preparation tetrahydrofurancarboxylic acid.COA of Formula: C6H10O3.

To develop a practical scalable approach to (R)-tetrahydrofuran-2-carboxylic acid (I), a chiral building block for furopenem, enantioselective hydrolysis of its esters is explored: When Et (±)-tetrahydrofuran-2-carboxylate (II, 2 M, 288 g/L) is digested by an Aspergillus melleus protease {0.2% (w/v)} in a 1.5 M potassium phosphate buffer (pH 8) for 20 h, enantioselective hydrolysis proceeds with E = 60 to give I in 94.4% ee. On separation from the leftover antipodal (S)-II by partition, I is treated with dicyclohexylamine in Me Et ketone/methanol (5:1) to precipitate the crystalline salt that contains I of >99% ee in 22% overall yield from II.

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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 《Condensation of aromatic aldehydes with glycine and acetylglycine》. Authors are Dakin, H. D..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).Formula: C8H12O4. Through the article, more information about this compound (cas:610-09-3) is conveyed.

The condensation referred to in the title is complicated by a competing reaction between CH2(NH2)CO2H and BzH, forming a non-acetylated derivative possibly of a type resembling a Schiff base. The 2 reactions are shown thus: (1) H2NCH2CO2H → AcNHCH2CO2H → MeC:N.C(:CHPh).CO.O → MeCONHC(:CHPh)CO2H, (2) HO2CCH2NH2 + BzH → HO2CCH2N:-CHPh (I) or O.CO.CH2.NH.CHPh. I may be called benzylideneglycine and was isolated and analyzed. Because the 2nd condensation product is a non-acetylated compound its formation can be largely suppressed by acetylating the glycine before the reaction. Correspondingly larger yields of the azlactone of α-acetamidocinnamic acid were obtained. Acetylation was most easily effected by warming glycine suspended in 3 parts of glacial AcOH with the theoretical amount of Ac2O until solution was obtained. A variety of aldehydes was used although the product from salicyl aldehyde was the most interesting. AcOC6H4CH:C.N:CMe.O.CO (II) → HOC3H4CH:C(NHAc)CO2H (III) → O.C6H4.CH:C(NHAc).CO (IV). II on treating with alkali and subsequent acidification forms the transient III which quickly passes over to IV. Detailed exptl. data are given.

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