Tag: M.W=200-250

Rong, Nianxin; Yuan, Yongsheng; Chen, Huijie; Yao, Changguang; Li, Teng; Wang, Yantao; Yang, Weiran published the artcile< A practical route to 2-iodoanilines via the transition-metal-free and base-free decarboxylative iodination of anthranilic acids under oxygen>, Related Products of 20776-50-5, the main research area is iodoaniline regioselective preparation; anthranilic acid oxygen decarboxylative iodination.

A simple and practical procedure for synthesizing 2-iodoanilines ArNH2 [Ar = 2-IC6H4, 2-I-4-BrC6H3, 2-I-4-MeOC6H3, etc.] had been developed. A series of highly regioselective 2-iodoanilines ArNH2 was obtained in satisfactory to good yields (of up to 90%) by carrying out the decarboxylative iodination of readily available anthranilic acids with inexpensive KI and I2 as halogen donors under transition-metal-free and base-free conditions. Oxygen was shown to be necessary for the transformation. This practical decarboxylative iodination route was operationally scalable and shown to exhibit high functional-group tolerance. Control experiments suggested that a radical pathway was involved in the transformation.

Organic Chemistry Frontiers published new progress about Aromatic amines Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 20776-50-5 belongs to class bromides-buliding-blocks, and the molecular formula is C7H6BrNO2, Related Products of 20776-50-5.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Xuan, Yi-ning; Chen, Zhen-yu; Yan, Ming published the artcile< An organocatalytic cascade reaction of 2-nitrocyclohexanone and α,β-unsaturated aldehydes with unusual regioselectivity>, Name: 3-(4-Bromophenyl)acrylaldehyde, the main research area is nitrocyclohexanone aldehyde unsaturated organocatalyst conjugate addition Henry reaction; nonanone bicyclo stereoselective preparation.

An organocatalytic cascade reaction of 2-nitrocyclohexanone and α,β-unsaturated aldehydes was developed. Bicyclo[3.3.1]nonanone products, e.g., I, were obtained with good yields and excellent enantioselectivities. The reaction occurred with unusual regioselectivity. A dienolate-iminium activation mechanism was proposed. The products were transformed to eight-membered cyclic ketones, e.g., II, with high enantioselectivity.

Chemical Communications (Cambridge, United Kingdom) published new progress about Bicyclic compounds, ketones Role: SPN (Synthetic Preparation), PREP (Preparation). 3893-18-3 belongs to class bromides-buliding-blocks, and the molecular formula is C9H7BrO, Name: 3-(4-Bromophenyl)acrylaldehyde.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Viana, Hugo; Carreiro, Elisabete P.; Goth, Albertino; Bacalhau, Patricia; Caldeira, Ana Teresa; Martins, Maria do Rosario; Burke, Anthony Joseph published the artcile< Sequential alcohol oxidation/putative homo Claisen-Tishchenko-type reaction to give esters: a key process in accessing novel biologically active lactone macrocycles>, SDS of cas: 135999-16-5, the main research area is diether ester preparation acetylcholinesterase butyrylcholinesterase inhibitor; aryloxyethyl alc tandem PCC oxidation Claisen Tishchenko esterification; lactone macrocycle preparation; borylated diether ester regioselective preparation Suzuki Miyaura coupling.

Application of a sequential pyridinium chlorochromate (PCC) alc. oxidation/putative Cr-catalyzed Claisen-Tishchenko reaction of primary alcs. to provide diether-esters, e.g., I was reported. The reaction could be conducted with 1 equiv of PCC and 1 equiv of BF3·OEt2. Indications based on literature precedent were that the reaction might proceed via a sequential alc. oxidation to the aldehyde followed by a putative Cr or boron catalyzed Claisen-Tishchenko-type reaction. Using this efficient methodol., a family of novel diether-esters was synthesized in very good yields; some of these mols. were subsequently tested against both acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE). In addition, a new synthetic strategy for the synthesis of lactone macrocycles with potential biol. activity was also disclosed. This methodol. included the regioselective borylation of the ester substrate and a subsequent Suzuki-Miyaura coupling to obtain the desired lactone macrocycle.

RSC Advances published new progress about Borylation. 135999-16-5 belongs to class bromides-buliding-blocks, and the molecular formula is C7H7BrO2, SDS of cas: 135999-16-5.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Tang, Shi; Xu, Zhen-Hua; Liu, Ting; Wang, Shuo-Wen; Yu, Jian; Liu, Jian; Hong, Yu; Chen, Shi-Lu; He, Jin; Li, Jin-Heng published the artcile< Radical 1,4-Aryl Migration Enabled Remote Cross-Electrophile Coupling of α-Amino-β-Bromo Acid Esters with Aryl Bromides>, Synthetic Route of 401-78-5, the main research area is arylated amino acid ester regioselective diastereoselective preparation; aminobromo acid ester aryl bromide tandem coupling nickel catalyst; amino acid esters; cross-electrophile coupling; nickel radical relay; radical aryl migration.

Here an unprecedented, efficient nickel-catalyzed radical relay was reported for the remote cross-electrophile coupling of β-bromo-α-benzylamino acid esters with aryl bromides via 1,4-aryl migration/arylation cascades. β-Bromo-α-benzylamino acid esters were considered as unique mol. scaffolds allowing for aryl migration reactions, which were conceptually novel variants for the radical Truce-Smiles rearrangement. This reaction enabled the formation of two new C(sp3)-C(sp2) bonds using a bench-stable Ni/bipyridine/Zn system featuring a broad substrate scope and excellent diastereoselectivity, which provided an effective platform for the remote aryl group migration and arylation of amino acid esters via redox-neutral C(sp3)-C(sp2) bond cleavage. Mechanistically, this cascade reaction was accomplished by combining two powerful catalytic cycles consisting of a cross-electrophile coupling and radical 1,4-aryl migration through the generation of C(sp3)-centered radical intermediates from the homolysis of C(sp3)-Br bonds and the switching of the transient alkyl radical into a robust α-aminoalkyl radical.

Angewandte Chemie, International Edition published new progress about Amino acid esters Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 401-78-5 belongs to class bromides-buliding-blocks, and the molecular formula is C7H4BrF3, Synthetic Route of 401-78-5.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Wu, Guojiao; Deng, Yifan; Wu, Chaoqiang; Zhang, Yan; Wang, Jianbo published the artcile< Synthesis of α-Aryl Esters and Nitriles: Deaminative Coupling of α-Amino-Esters and α-Aminoacetonitriles with Arylboronic Acids>, Safety of Ethyl 2-(3-bromophenyl)acetate, the main research area is nitrile benzeneacetonitrile preparation; benzeneacetic areneacetic acid ester preparation; arenes; boron; diazo compounds; nitriles; synthetic methods.

Transition-metal-free synthesis of α-aryl esters and nitriles using arylboronic acids with α-amino esters and α-(amino)acetonitrile derivatives, resp., as starting materials has been developed. The reaction represents a rare case of converting C(sp3)-N bonds (carbon-nitrogen bonds) into C(sp3)-C(sp2) bonds (carbon-carbon bonds). The reaction conditions are mild, demonstrate good functional-group tolerance, and can be scaled up. The synthesis of the target compounds was achieved using glycine ester hydrochloride, leucine ester hydrochloride, aspartate ester hydrochloride, alanine ester hydrochloride as starting materials in a reaction with (aryl)boronic acids. The title compounds thus formed included benzeneacetic acid esters, 1-naphthaleneacetic acid ester, benzenepropanoic acid esters, α-phenyl-1H-indole-3-propanoic acid ester, benzenebutanoic acid ester and similar substances. A reaction of (aryl)boronic acids with α-(amino)acetonitrile gave α-(alkyl)benzeneacetonitrile derivatives Nitriles included α-(hexyl)benzeneacetonitrile, α-phenyl-3-thiophenepropanenitrile and similar compounds

Angewandte Chemie, International Edition published new progress about Amino acid esters Role: RCT (Reactant), RACT (Reactant or Reagent). 14062-30-7 belongs to class bromides-buliding-blocks, and the molecular formula is C10H11BrO2, Safety of Ethyl 2-(3-bromophenyl)acetate.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Mel’nikov, N. N.; Turetskaya, R. Kh.; Baskakov, Yu. A.; Boyarkin, A. N.; Kuznetsova, M. S. published the artcile< The structure and the physiological activity of substituted phenylacetic and naphthylacetic acids>, Product Details of C9H9BrO2, the main research area is .

Introduction of halogen into the ring of PhCH2CO2H increases the physiol. activity, which is greatest with Cl; Br is less active; iodine in the p-position does not increase activity. Most active are the 2-halo, least active the 4-halo derivatives, while the 3-halo derivatives are intermediate. This is the reverse order of activity in comparison with phenoxyacetic acids. Introduction of a 2nd halogen does not change the physiol. activity, while a 3rd halogen can either reduce or increase activity. A Me group in the p-position reduces the activity, and 3 Me groups reduce it very much. A smaller decrease in activity is caused by a p-MeO group. Halogenation of m-MeC6H4OCH2CO2H causes increased activity, the greatest activity resulting from 4-substitution, and lesser activity from 2-halogenation. With 2,4-D as the standard which gave 100% increase of wheat coleoptile growth at 1 mg./l. concentration, and heteroauxin as the standard which gave 100% increase of kidneybean root growth, the following physiol. results were obtained in plant tests; (in above order, with 1, 10, and 100 mg./l. concentrations tested for the wheat growth, and 10, 50 and 100 mg./l. concentrations for the kidney bean growth). Substituted phenylacetic acids (substituents given): H, m. 76°, -2%, +45%, -, -, +4%, 0%; ο-Cl, m. 95°, +70%, +84%, – +5%, +150%, -; m-Cl, m. 74°, +9%, +61%, -, -, +62%, +260%; p-Cl, m. 106°, +13%, +71%, -, -, +55%, +91%; ο-Br, m. 104°, +7%, +71%, -, -, +33%, +104%; p-Br, m. 114°, +2%, +80%, -, -, 0%, +8%; p-I, m. 135°, -4%, -6%, -, -, 0%, +21%; 2,4-di-Cl, m. 131°, +10%, +80%, -, -, +58%, +162%; 2,5-di-Cl, m. 105°, +13%, +80%, -, -, +30%, +120%; 2,3,4-tri-Cl, m. 136°, +40%, +71%, -, -, +150%, -60%; 2,4,5-tri-Cl analog, m. 126°, 0%, +56%, -, -, +98%, +100%; p-MeO, m. 83°, -, +20%, +20%, -, 0%, 0%; p-Me, m. 92°, -, +5%, +6%, -, 0%, 0%; 4,3-ClMe, m. 83°, +22%, +73%, -, -, +7%, +69%; 4,3-BrMe, m. 81°, +20%, +71%, -, -, 14%, +90%; 6,3-ClMe, m. 86°, -2%, +40%, -, -, 0%, -25%; 6,3-BrMe, m. 82°, -8%, +59%, -, -, +66%, +66%;, 2,4-ClMe, m. 106°, +13%, +44%, -, -, +12%, +33%; 3,4-Me(MeO), m. 127°, -, +1%, +34%, -, 0%, 0%; 2,4,5-Tri-Me, m. 117°, -, +3%, -6%, -, -21%, -25%; 2,4-Me(MeO), m. 107°, -, -12%, +25%, -, 0%, 0%. In substituted naphthylalkylcarboxylic acids it was shown that removal of CO2H from the ring by more than 1 C atom reduces the physiol. activity and the compounds with an acid group at the 1-position on C10H8 skeleton are the only active ones; substances with 2-substitution are inactive. Substitution of alkyl groups or MeO groups into the C10H8 ring leads to sharp decline in activity. The following results were obtained in biol. tests (same standards as above): Substituted 1-naphthaleneacetic acids (substituents given): H, m. 131°, +77%, + 169%, -, -, +92%, -; 4-MeO, m. 144°, +2%, -12%, -, +10%, +27%, +9%; 4-Me, m. 148°, +1%, +1%, +4%, +36%, +24%, -10%; 4-Et, m. 129°, +9%, -, -, +9%, +6%, +27%; 4-Pr, m. 119°, -5%, -7%, -, +24%, +50%, +32%; 4-Bu, m. 110°, -, -14%, -, +21%, +20%, +33%. 1-C10H7COCH2CH2CO2H, m. 132°, +9%, +60%, -, -, -, -; 1-C10H7(CH2)3CO2H, m. 1602, +9%, +46%, -, -, -, -; 2-C10H7COCH2CH2CO2H, m. 174°, -25%, -9%, -, -, -, -, 2-C10H7(CH2)3CO2H, m. 109°, -3%, -5%, -, -, -, -. Most of the above acids were prepared by the Willgerodt reaction others through the nitriles from the corresponding benzyl halides.

Doklady Akademii Nauk SSSR published new progress about Halogens. 215949-57-8 belongs to class bromides-buliding-blocks, and the molecular formula is C9H9BrO2, Product Details of C9H9BrO2.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Mhadhbi, Oumaima; Liu, Linhao; Benzai, Amal; Mellah, Besma; Besbes, Neji; Ollivier, Jerome; Cordier, Marie; Doucet, Henri published the artcile< Palladium-catalyzed direct C5-arylation or C4,C5-diarylation of 2-alkylisothiazol-3-ones>, Reference of 401-78-5, the main research area is aryl alkylisothiazolone preparation regioselective; alkylisothiazolone aryl bromide paladium catalyst arylation.

The regioselectivity of the Pd-catalyzed direct arylation of unsubstituted 2-alkylisothiazol-3(2H)-ones was investigated. Conditions for the regioselective palladium-catalyzed direct C5-arylation of 2-alkylisothiazol-3-ones using aryl bromides as the coupling partners are reported. This procedure tolerates a wide variety of substituents such as nitro, nitrile, ester, chloro, fluoro, trifluoromethyl, trifluoromethoxy, difluoromethoxy at para-, meta- and also ortho-positions on the aryl bromide. Both methyl- and octyl-substituents at 2-position of alkylisothiazol-3-ones are tolerated. Moreover, at a more elevated temperature in the presence of a larger excess of the aryl bromide, the access to the C4,C5-diarylated alkylisothiazol-3-ones is also possible, revealing that the C4-position of isothiazol-3(2H)-ones is reactive for direct arylation when the C5-position is blocked. Therefore, this method provides a one pot access to a wide variety of isothiazolinone derivatives allowing to modify easily their biol. properties.

Tetrahedron published new progress about Aryl bromides Role: RCT (Reactant), RACT (Reactant or Reagent). 401-78-5 belongs to class bromides-buliding-blocks, and the molecular formula is C7H4BrF3, Reference of 401-78-5.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Mo, Di-Wei; Dong, Shuai; Sun, Haiyan; Chen, Jia-Sheng; Pang, Jian-Xin; Xi, Bao-Min; Chen, Wen-Hua published the artcile< Synthesis and potent inhibitory activities of carboxybenzyl-substituted 8-(3-(R)-aminopiperidin-1-yl)-7-(2-chloro/cyanobenzyl)-3-methyl-3,7-dihydro-purine-2,6-diones as dipeptidyl peptidase IV (DPP-IV) inhibitors>, Quality Control of 85070-57-1, the main research area is dihydropurinedione derivative preparation dipeptidyl peptidase IV inhibitory activity; 3-Methyl-3,7-dihydro-purine-2,6-dione; Diabetes; Dipeptidyl peptidase IV inhibitor; Inhibitory activity; Synthesis.

Fourteen 3-methyl-3,7-dihydro-purine-2,6-dione derivatives bearing carboxybenzyl and 2-chloro/cyanobenzyl groups at the N-1 and N-7 positions, resp., were synthesized as dipeptidyl peptidase IV (DPP-IV) inhibitors. These compounds were characterized on the basis of NMR (1H and 13C) and ESI MS data. In vitro bioassay indicates that most of these compounds showed moderate to good inhibitory activities against DPP-IV. Among them, compound I (IC50 = 36 nM) exhibited comparable activity with a pos. control, Sitagliptin (IC50 = 16 nM). In addition, the structure-activity relationship of these compounds is also briefly discussed.

Bioorganic & Medicinal Chemistry Letters published new progress about Antidiabetic agents. 85070-57-1 belongs to class bromides-buliding-blocks, and the molecular formula is C9H8BrFO2, Quality Control of 85070-57-1.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Klett, Johannes; Wozniak, Lukasz; Cramer, Nicolai published the artcile< 1,3,2-Diazaphospholene-Catalyzed Reductive Cyclizations of Organohalides>, Recommanded Product: 2-Bromo-4-(trifluoromethyl)phenol, the main research area is dihydrobenzofurane pyrrolidine preparation photochem; aryl alkyl halide reductive cyclization diazaphospholene hydride catalyst; Cyclizations; Diazaphospholenes; Homogeneous Catalysis; Photocatalysis; Radical Reactions.

1,3,2-Diazaphospholene hydrides (DAP-Hs) are highly nucleophilic organic hydrides serving as main-group catalysts for a range of attractive transformations. DAP hydrides can act as stoichiometric hydrogen atom transfer agents in radical reactions. Herein, authors report a DAP-catalyzed reductive radical cyclization of a broad range of aryl and alkyl halides under mild conditions. The pivotal DAP catalyst turnover was achieved by a DBU-assisted σ-bond metathesis between the formed DAP halide and HBpin, which rapidly regenerates DAP-H. The transformation is significantly accelerated by irradiation with visible light. Mechanistic investigations indicate that visible light irradiation leads to the formation of DAP dimers, which are in equilibrium with DAP radicals and accelerate the cyclization. The direct use of (DAP)2 enabled a catalytic protocol in the absence of light.

Angewandte Chemie, International Edition published new progress about Anilines Role: RCT (Reactant), RACT (Reactant or Reagent). 81107-97-3 belongs to class bromides-buliding-blocks, and the molecular formula is C7H4BrF3O, Recommanded Product: 2-Bromo-4-(trifluoromethyl)phenol.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Rueping, Magnus; Sugiono, Erli; Merino, Estibaliz published the artcile< Asymmetric iminium ion catalysis: an efficient enantioselective synthesis of pyranonaphthoquinones and β-lapachones>, Safety of 3-(4-Bromophenyl)acrylaldehyde, the main research area is asym synthesis pyranonaphthoquinone addition cyclization aliphatic aromatic aldehyde hydroxynaphthoquinone; lapachone derivative asym synthesis pyranonaphthoquinone.

An addition-cyclization reaction cascade triggered by an organocatalyst was used for the enantioselective preparation of a series of biol. active 1,2- and 1,4-pyranonaphthoquinones, e.g. I, from aliphatic and aromatic α,β-unsaturated aldehydes and 2-hydroxy-1-4-naphthoquinone. A trimethylsilyl-protected diarylprolinol serves as the Lewis base organocatalyst.

Angewandte Chemie, International Edition published new progress about Addition reaction catalysts. 3893-18-3 belongs to class bromides-buliding-blocks, and the molecular formula is C9H7BrO, Safety of 3-(4-Bromophenyl)acrylaldehyde.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary