Month: April 2022

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: 6797-13-3, is researched, Molecular C9H9NO, about Direct α-Chalcogenation of Aliphatic Carboxylic Acid Equivalents, the main research direction is alpha chalcogenation aliphatic carboxylic acid; thioether selenoether preparation copper catalyzed chalcogenation.Product Details of 6797-13-3.

A novel approach to α-chalcogenation of aliphatic carboxylic acids has been developed by means of transforming them as the corresponding benzazoles. The catalyst system, consisting of CuI, DMSO, and a base, operates through a unique mechanism to access a range of practically significant thio- and selenoethers that are otherwise challenging to achieve. The applicative potentials have been exemplified by utilizing the resultant chalcogenated compounds as the precursor for the synthesis of biol. pertinent mols. and synthetic intermediates.

This compound(2-Ethylbenzo[d]oxazole)Product Details of 6797-13-3 was discussed at the molecular level, the effects of temperature and reaction time on the properties of the compound were discussed, and the optimum reaction conditions were selected.

Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

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-Mercapto-5-methylbenzimidazole, is researched, Molecular C8H8N2S, CAS is 27231-36-3, about In vitro metabolism of 4-methyl- and 5-methyl-2-mercaptobenzimidazole, thyrotoxic and hepatotoxic rubber antioxidants, in rat liver microsomes.Application In Synthesis of 2-Mercapto-5-methylbenzimidazole.

The metabolism of 4-methyl-2-mercaptobenzimidazole (4-MeMBI), 5-methyl-2-mercaptobenzimidazole (5-MeMBI), and 2-mercaptobenzimidazole (MBI) was examined in vitro in rat liver microsomes. The test chems. were incubated in the presence of liver microsomes from male Sprague-Dawley rats, and their metabolism was analyzed by HPLC. The metabolism amount increased in an incubation time-dependent manner, and was similar among the test chems. SKF-525A, a non-selective inhibitor of cytochrome P 450 (CYP) enzymes, decreased the metabolic rate of all the test chems., indicating the involvement of liver microsomal CYP enzymes. When liver microsomes from rats treated with CYP-inducers (β-naphthoflavone, phenobarbital, and isoniazid) were used, 4-MeMBI was more decreased than 5-MeMBI, particularly in the phenobarbital-treated group. These results, together with the reported inducibility of the drug-metabolizing activity by the test chems., partly explained the counteraction in the toxic effects between 4-MeMBI and 5-MeMBI in the in vivo study.

This compound(2-Mercapto-5-methylbenzimidazole)Application In Synthesis of 2-Mercapto-5-methylbenzimidazole was discussed at the molecular level, the effects of temperature and reaction time on the properties of the compound were discussed, and the optimum reaction conditions were selected.

Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

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-Mercapto-5-methylbenzimidazole, is researched, Molecular C8H8N2S, CAS is 27231-36-3, about 2-(3-Bromo-1-phenylsulfonyl-RH-indol-2-ylmethylsulfanyl)-6-methyl-1H-benzimidazole.Computed Properties of C8H8N2S.

In the title compound, C23H18BrN3O2S2, the sulfonyl-bound Ph ring and benzimidazole moiety are nearly orthogonal to the indole ring system. The mol. structure is stabilized by C-H···Br and C-H···O H bonding interactions. In the crystal structure, glide-related mols. are linked by N-H···N H bonds to form chains along the c axis and adjacent chains are interlinked by C-H···π interactions into a three-dimensional network. Crystallog. data are given.

This compound(2-Mercapto-5-methylbenzimidazole)Computed Properties of C8H8N2S was discussed at the molecular level, the effects of temperature and reaction time on the properties of the compound were discussed, and the optimum reaction conditions were selected.

Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

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: 96651-85-3, is researched, Molecular C13H18ClN, about Spirovesamicols: Conformationally Restricted Analogs of 2-(4-Phenylpiperidino)cyclohexanol (Vesamicol, AH5183) as Potential Modulators of Presynaptic Cholinergic Function, the main research direction is spirovesamicol preparation vesamicol receptor ligand structure; cholinergic neurotransmission spirovesamicol vesamicol receptor ligand.SDS of cas: 96651-85-3.

In an effort to develop selective inhibitors of vesicular acetylcholine storage, the authors have synthesized a series of semirigid vesamicol receptor ligands based on the structure of 2-(4-phenylpiperidino)cyclohexanol (vesamicol, AH5183). In these compounds, the planes of the Ph and piperidyl moieties of the parent ligand vesamicol are held at right angles by vinyl, ethylene, and propylene bridges to form N-substituted derivatives of spiro[indene-1,4′-piperidine], 2,3-dihydrospiro[indene-1,4′-piperidine], and 3,4-dihydrospiro[naphthalene-1(2H),4′-piperidine], resp. Preliminary evaluation of these compounds in elec. organ synaptic vesicles revealed several potent vesamicol receptor ligands, such as1′-(2-hydroxy-1,2,3,4-tetrahydronaphth-3-yl)spiro[1H-indene-1,4′-piperidine] and 1′-(2-hydroxy-1,2,3,4-tetrahydronaphth-3-yl)spiro[2-bromo-1H-indene-1,4′-piperidine], which display subnanomolar affinity for this receptor. In general, the vinyl and ethylene bridges yielded the most potent analogs while the propylene-bridged analogs were among the least potent compounds The increased rigidity of these spiro-fused compounds, relative to the corresponding simple 4-phenylpiperidine derivatives of vesamicol, is expected to confer greater selectivity for the vesamicol receptor.

This compound(2,3-Dihydrospiro[indene-1,4′-piperidine] hydrochloride)SDS of cas: 96651-85-3 was discussed at the molecular level, the effects of temperature and reaction time on the properties of the compound were discussed, and the optimum reaction conditions were selected.

Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Liu, Xing; Liu, Min; Xu, Wan; Zeng, Meng-Tian; Zhu, Hui; Chang, Cai-Zhu; Dong, Zhi-Bing published an article about the compound: 2-Mercapto-5-methylbenzimidazole( cas:27231-36-3,SMILESS:SC1=NC2=CC(C)=CC=C2N1 ).Formula: C8H8N2S. 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:27231-36-3) through the article.

An efficient and practical method for the one-step synthesis of benzothiazole-2-thiols I [R = H, 5-Cl; X = S], benzoxazole-2-thiols I [R = H, 5-Me, 5-Br, etc.; X = O] and benzimidazoline-2-thiones such as II by cyclization of 2-aminothiophenols, 2-aminophenols, and 1,2-phenylenediamines with tetramethylthiuram disulfide (TMTD) in water was described. This method was also used for the synthesis of 4,5-dihydro-thiazole-2-thiol, 4,5-dihydro-oxazole-2-thiol and 1,3-ethylenethiourea from their corresponding aliphatic amines and (TMTD). The features of this method included metal/ligand-free, excellent yield, short reaction time and broad substrate scope. The method provided a facile and convenient preparation of some potentially biol. active compounds

This compound(2-Mercapto-5-methylbenzimidazole)Formula: C8H8N2S was discussed at the molecular level, the effects of temperature and reaction time on the properties of the compound were discussed, and the optimum reaction conditions were selected.

Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Benzoxazole derivatives》. Authors are Skraup, Siegfried; Moser, Marie.The article about the compound:2-Ethylbenzo[d]oxazolecas:6797-13-3,SMILESS:CCC1=NC2=CC=CC=C2O1).Category: benzoxazole. Through the article, more information about this compound (cas:6797-13-3) is conveyed.

cf. C. A. 14, 926. In the continuation of the study of the opening of the ring of benzoxazole (A) and its homologs a number of interesting observations were made which seem to be characteristic of the A system. All attempts to prepare benzoxazole-2-nitrile from the 2-NH2 derivative through the diazonium compound failed; after the treatment with HNO2, the amine does, to be sure, give a distinct violet color with R-salt, but the greater part of the amine is always recovered unchanged. A decisive proof of the aromatic nature of A derivatives, however, is found in the oxidation of 2-methyl-benzoxazole to benzoxazole-2-carboxylic acid (B), which can be obtained in better yield by the oxidation of 2-o-hydroxyphenylbenzoxazole (C). Instead of reacting normally to form a ketone with Grignard reagents, the chloride of B to a great extent, the anilide exclusively, exerts an energetic reducing action. The chloride with PhMgBr gives chiefly benzoxazylmethyl alc. (D), together with a little benzoxazyldiphenylcarbinol (E), probably formed by combination of a 2nd mol. of the PhMgBr with the primary intermediate ketone; E in concentrated H2SO4 exhibits deep red halochromism phenomena, another fact indicative of the aromatic nature of the A derivatives The anilide with MeMgI gives exclusively benzoxazole-2-aldehyde anil (F), undoubtedly formed by reduction of the tautomeric form O.C6H4.N:CC(OH):NPh of the anilide; contrary to other Schiff bases, F is hardly attacked by acids but easily decomposed into the aldehyde and PhNH2 by alkalies. The desired benzoxazyl Ph ketone (G) was finally obtained from its oxime which in turn was prepared from 2-benzylbenzoxazole (H). The velocity of hydrolysis of a further number of 2-substituted derivatives of A has been measured; the reaction is apparently monomol. (the H2O being present in excess) and in all but the Bz and PhCH2 derivatives the velocity constants found agreed with those calculated for a monomol. reaction. Below are given, after the substituent, the time in min. and the velocity constant (0.4343k): At 19°: H, 1, 0.0915. At 61°: PhCH2, 29, 0.0094; 120, 0.0031; Et, 30, 0.0033; 128, 0.0031; Me, 60, 0.00279; 120, 0.00279. At 108°: Me, 5, 0.0926; 20, 0.0848; m-O2NC6H4, 372, 0.0059; Bz, 58, 0.0047; 121, 0.0023; Ph, 134, 0.0019; 360, 0.0017; p-MeOC6H4, 371, 0.00067; 887, 0.00066; β-naphthyl, 479, 0.00058; 936, 0.00049; α-naphthyl, 436, 0.00024; 1024, 0.00019; o-HOC6H4, 960, 0.00024; 2450, 0.00013; p-O2NC6H4, 1100, 0.00010; 2615, 0.00005. The sharp difference between aliphatic and aromatic radicals, which had already been pointed out, is clear. Also, the velocity of hydrolysis of the Et is somewhat greater than that of the Me derivative, i. e., the valence demand (see S. and Freundlich C. A. 16, 3646) of Et is smaller than that of Me, in accordance with Meerwein’s observation that alkyls with an odd number of C atoms have a greater affinity demand than those with an even number The great difference between the unsubstituted A and its Me homolog shows that in this respect (valence demand), also, H occupies a peculiar position, which certainly is closely connected with the differing properties of the initial members of homologous series (HCO2H, HCHO, differences between aldehydes and ketones, etc.). The temperature coefficient of the reaction as determined for the Me derivative (2.07 according to the Berthelot, 4015 according to the Arrhenius formula) is strikingly small as compared with those usually found for apparently monomol. reactions. C, obtained in 53% yield from equimol, amounts of and o-H2NC6H4OH and o-HOC6H4CONH2 fused together until the temperature rises to 200° and NH3 is no longer evolved (about 1.5 h.), long needles with a pink tinge from alc., m. 123°, soluble in organic solvents generally with a strong fluorescence, in AcOH with red-violet color, difficulty in alkali with violet fluorescence; in KOH with KMnO4 on the H2O-bath it gives 48% of the potassium salt, golden yellow leaflets, of B, white precipitate, m. 85°, loses CO2 with formation of A on the H2O-bath, also when heated with 20% HCl but not with boiling alkalies. Chloride, obtained in 93.7% yield from the K salt and SOCl2 on the H2O -bath, m. 85°, has an unpleasant penetrating odor; 4 g. in Et2O cautiously treated with the calculated amount of PhMgBr, boiled 1 h. and allowed to stand overnight yields a product separated by means of cold alc. into 0.3 g. E, m. 157°, and D (obtained exclusively if the PhMgBr is added to a hot solution of the chloride), m. 125°, b14 200-30°. Anilide of B, m. 156-7°. F (5 g. from 10 g. of the anilide with MeMgI), m. 153°. Refluxed 1 h. in alc. with 3.7 g. ONC6H4NMe2 and 3 cc. of 35% NaOH, 5 g. H gives 5 g. of the compound O.C6H4.N:CCPh: NC6H4NMe2, fine needles from alc., begins to decompose 150°. The compound O.C6H4.N:CCPh:NNHC6H3(NO2)2 (1.5 g. from 1.5 g. H in AcOH allowed to stand 12 h. with 2,4-(O2N)2C6H3N:NSO4H), yellow crystals from PhMe, m. 140°. Oxime of G (18 g. from 20 g. H in cold Et2O, 10 g. NaOEt and 15 g. AmNO2. shaken several hrs., filtered, dissolved in NaOH, freed from AmOH with Et2O and precipitated with CO2), crystals from 50% alc., m. 193°; 4 g. heated 2 h. at 180-90° in a sealed tube with 40 g. AcOH (dehydrated by freezing twice and distilling over P2O5), gives 2-2.5 g. G, soluble with golden yellow color in concentrated H2SO4 or HCl, reprecipitated by H2O. 2-Ethylbenzoxazole, from o-H2NC6H4OH and EtCN heated 24 h. at 205-10°, b. 210°, d20 1.081. 2-β-Naphthylbenzoxazole, from o-H2NC6H4OH and β-C10H7CN boiled 8 h., m. 115-6°, fluoresces strongly in 2-p-Nitrophenylbenzoxazole (1 g. from H2NC6H4OH and 5 g. O2NC6H4CN heated 1 h. at 135-40° and sublimed through filter paper), long needles with pink tinge from CHCl3, m. 260°, soluble in hydrocarbons with intense green fluorescence. The o- and m-compounds cannot be prepared in this way; that a derivative of A is formed is indicated by the intense green fluorescence of the solution of the product in petr. ether, which, however, dissolves but traces of it; vacuum distillation leads to decomposition and only traces of a high boiling product are obtained; raising the temperature of the condensation reaction or using a higher boiling solvent (cumene, PhCl) also results in decomposition The m-compound was prepared by Ransom’s method (Am. Chem. J. 23, 24 (1900)) (yield, 4.5%). All the hydrolysis velocity measurements were made with 20.2% HCl.

This compound(2-Ethylbenzo[d]oxazole)Category: benzoxazole was discussed at the molecular level, the effects of temperature and reaction time on the properties of the compound were discussed, and the optimum reaction conditions were selected.

Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Name: 2-Ethylbenzo[d]oxazole. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: 2-Ethylbenzo[d]oxazole, is researched, Molecular C9H9NO, CAS is 6797-13-3, about Metal free montmorillonite KSF clay catalyzed practical synthesis of benzoxazoles and benzothiazoles under aerobic conditions. Author is Kummari, Vijaya Babu; Chiranjeevi, Kalavakuntla; Suman Kumar, Alleni; Aravind Kumar, Rathod; Yadav, Jhillu Singh.

An efficient method for the synthesis of benzoxazoles and benzothiazoles I [R = Cl, Me, NO2, t-Bu; R1 = Me, Et, i-Pr; X = O, S] via montmorillonite KSF clay catalyzed condensation reaction of β-diketones and 2-aminophenols or 2-aminothiophenols resp. was reported. The efficiency of the reaction reflected from the wide substrate scope with electronic differentiation on aryls. The reaction was metal free and proceeded without the exclusion of air or moisture, and further the catalyst could be recycled up to 3-5 catalytic cycles.

This compound(2-Ethylbenzo[d]oxazole)Name: 2-Ethylbenzo[d]oxazole was discussed at the molecular level, the effects of temperature and reaction time on the properties of the compound were discussed, and the optimum reaction conditions were selected.

Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

SDS of cas: 481054-89-1. 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: Ethyl 6-bromoquinoline-3-carboxylate, is researched, Molecular C12H10BrNO2, CAS is 481054-89-1, about Synthesis of quinoline-3-carboxylates by a Rh(II)-catalyzed cyclopropanation-ring expansion reaction of indoles with halodiazoacetates. Author is Morten, Magnus; Hennum, Martin; Bonge-Hansen, Tore.

A novel synthesis of Et quinoline-3-carboxylates from reactions between a series of indoles and halodiazoacetates was reported. The formation of the quinoline structure was probably the result of a cyclopropanation at the 2- and 3-positions of the indole followed by ring-opening of the cyclopropane and elimination of H-X.

This compound(Ethyl 6-bromoquinoline-3-carboxylate)SDS of cas: 481054-89-1 was discussed at the molecular level, the effects of temperature and reaction time on the properties of the compound were discussed, and the optimum reaction conditions were selected.

Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Phua, Pim Huat; White, Andrew J. P.; de Vries, Johannes G.; Hii, King Kuok published the article 《Enabling ligand screening for palladium-catalyzed enantioselective aza-Michael addition reactions》. Keywords: parallel ligand screening stereoselective aza Michael addition palladium; carbamate oxoalkenyl amine Michael addition parallel ligand screening palladium; benzamide oxoalkenyl amine Michael addition parallel ligand screening palladium.They researched the compound: (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole( cas:503538-69-0 ).Electric Literature of C38H24F4O4P2. 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:503538-69-0) here.

The bis(trifluoromethanesulfonate)palladium(II) dihydrate complex, Pd(OTf)2·2 H2O (I), is an active palladium(II) precursor for the generation of dicationic palladium(II) catalysts. Parallel ligand screening is carried out for the first time and twenty-four chiral ligands were evaluated for the asym. aza-Michael addition of aromatic amines to (1-oxo-2-alkenyl)carbamic acid tert-Bu esters and N-[(2E)-1-oxo-2-alkenyl]benzamide derivatives Enantioselectivity of >99% can be obtained. Catalytic precursors generated from I using this new protocol have been identified.

This compound((R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole)Electric Literature of C38H24F4O4P2 was discussed at the molecular level, the effects of temperature and reaction time on the properties of the compound were discussed, and the optimum reaction conditions were selected.

Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Synthetic anticonvulsants. Preparation and properties of some benzoxazoles》. Authors are Bywater, W. G.; Coleman, W. R.; Kamm, Oliver; Merritt, H. Houston.The article about the compound:2-Ethylbenzo[d]oxazolecas:6797-13-3,SMILESS:CCC1=NC2=CC=CC=C2O1).Quality Control of 2-Ethylbenzo[d]oxazole. Through the article, more information about this compound (cas:6797-13-3) is conveyed.

The following benzoxazoles were prepared by heating mol. equivalents of tech. o-H2NC6H4OH and the appropriate acid, amide, or nitrile to boiling for several hrs.; the reaction mixture was distilled at atm. pressure and the crude product, if liquid, was dissolved in petr. ether and washed with 10% NaOH, which destroyed the characteristic fluorescence of the crude material. The solids were pulverized and washed with 10% alkali and H2O before crystallizing from dilute EtOH or Me2CO. The m.ps. and b.ps. are corrected AmCO2H gives 67.2% of 2-amylbenzoxazole, b2 125°, b. 264-6°; Et2CHCO2H gives 44.3% of the (1-ethylpropyl) analog, b1 110°, b. 250-2°; caprylic acid yields 61.5% of the heptyl analog, b4 174-5°, b. 294-8°; lauramide yields 30% of the hendecyl analog, b1 179-84°, b. 347-53°, m. 32-3°; oleic acid gives 38.6% of the 8-heptadecenyl analog, b2 248-9°; Ph2CHCO2H yields 55.1% of the (diphenylmethyl) analog, m. 69.5-70.5°; (CH2CO2H)2 gives 44.5% of 2,2′-ethylenedibenzoxazole, m. 194.5-5.5°. The following yields (%) were obtained of known 2-alkyl derivatives of benzoxazole: Et 50, hexyl 71.4, pentadecyl 26, heptadecyl 27.7, Ph 33.3, PhCH2 82.4 (from PhCH2CO2H), 40.6 (from PhCH2CN), p-ClC6H4 30.5, HO 35, styryl 4 [in this reaction a by-product b14 87-9° (HCl salt, m. 154-5°, N 8.2%, Cl 20.38%)]. Benzoxazolone results in 35% yield by fusing CO(NH2)2 with tech. o-H2NC6H4OH at 200°; BuNHCONH2 gives 10.2%; urethan gives 53%. Anticonvulsant activity [A, if the convulsive threshold is elevated to more than 50 ma., B, if increased by 20-30 ma. 2 hrs. after treatment; the figure is the dose (g./kg.) at which the rating was established] of 2-substituted benzoxazoles was determined as follows: Me, A, 0.5; Et, B, 0.37; Am, B, 0.15; (1-ethylpropyl), B, 0.25; hexyl, B, 1.0; heptyl, A, 0.38; pentadecyl, B, 0.41; benzyl, A, 0.3; benzimidazole, A, 0.47; dilantin Na, A, 0.05. Toxicity data (LD40) in g./kg. (white mice, orally): HO 0.94, Me 1.10, Et 1.0, Am 1.3, (1-ethylpropyl) 1.3, hexyl 2.75, heptyl 2.3, pentadecyl 5+, heptadecyl 10.5+, Ph 5+, benzyl 1.75, (p-chlorophenyl) 6, (diphenylmethyl) 0.05, 2-aminobenzimidazole 0.60, dilantin Na 0.5.

This compound(2-Ethylbenzo[d]oxazole)Quality Control of 2-Ethylbenzo[d]oxazole was discussed at the molecular level, the effects of temperature and reaction time on the properties of the compound were discussed, and the optimum reaction conditions were selected.

Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem