Month: October 2022

Zhang, Lei; Rogers, Bruce N.; Duplantier, Allen J.; McHardy, Stanley F.; Efremov, Ivan; Berke, Helen; Qian, Weimin; Zhang, Andy Q.; Maklad, Noha; Candler, John; Doran, Angela C.; Lazzaro, John T.; Ganong, Alan H. published the artcile< 3-(Imidazolylmethyl)-3-aza-bicyclo[3.1.0]hexan-6-yl)methyl ethers: A novel series of mGluR2 positive allosteric modulators>, Application In Synthesis of 6136-93-2, the main research area is imidazolylmethylazabicyclohexanol ether preparation metabotropic glutamate receptor modulator.

The synthesis and structure-activity relationship of a novel series of 3-(imidazolylmethyl)-3-azabicyclo[3.1.0]hexan-6-ylmethyl ethers, derived from a high throughput screening, are described. Subsequent optimization led to identification of potent, metabolically stable and orally available mGluR2 pos. allosteric modulators.

Bioorganic & Medicinal Chemistry Letters published new progress about Metabotropic glutamate receptor 2 Role: BSU (Biological Study, Unclassified), BIOL (Biological Study). 6136-93-2 belongs to class nitriles-buliding-blocks, and the molecular formula is C6H11NO2, Application In Synthesis of 6136-93-2.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Chatterjee, Arpita; Murmu, Chudamani; Peruncheralathan, S. published the artcile< Copper-catalysed N-arylation of 5-aminopyrazoles: a simple route to pyrazolo[3,4-b]indoles>, Recommanded Product: 2-(2-Bromo-5-fluorophenyl)acetonitrile, the main research area is phenylaminopyrazole preparation copper catalyst arylation; phenyl pyrazoloindole preparation.

A copper-catalyzed intramol. N-arylation of 5-aminopyrazoles is demonstrated for the first time. Highly substituted pyrazolo[3,4-b]indoles were synthesized. In particular, the indole core was decorated with halogens and alkyl and methoxy groups. Furthermore, a selective N-arylation of unsym. diaryl bromide containing pyrazoles was exemplified, resulting in valuable pyrazolo[1,5-a]benzimidazoles.

Organic & Biomolecular Chemistry published new progress about Aryl bromides Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 886761-96-2 belongs to class nitriles-buliding-blocks, and the molecular formula is C8H5BrFN, Recommanded Product: 2-(2-Bromo-5-fluorophenyl)acetonitrile.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Val, Cristina; Rodriguez-Garcia, Carlos; Prieto-Diaz, Ruben; Crespo, Abel; Azuaje, Jhonny; Carbajales, Carlos; Majellaro, Maria; Diaz-Holguin, Alejandro; Brea, Jose M.; Loza, Maria Isabel; Gioe-Gallo, Claudia; Contino, Marialessandra; Stefanachi, Angela; Garcia-Mera, Xerardo; Estevez, Juan C.; Gutierrez-de-Teran, Hugo; Sotelo, Eddy published the artcile< Optimization of 2-Amino-4,6-diarylpyrimidine-5-carbonitriles as Potent and Selective A1 Antagonists>, Quality Control of 21667-62-9 , the main research area is amino diarylpyrimidin carbonitrile preparation adenosine receptor SAR docking.

Herein, document of a large collection of 108 2-amino-4,6-disubstituted-pyrimidine derivatives as potent, structurally simple, and highly selective A1AR ligands. The most attractive ligands were confirmed as antagonists of the canonical cyclic adenosine monophosphate pathway, and some pharmacokinetic parameters were preliminarilly evaluated. The library, built through a reliable and efficient three-component reaction, comprehensively explored the chem. space allowing the identification of the most prominent features of the structure-activity and structure-selectivity relationships around this scaffold. These included the influence on the selectivity profile of the aromatic residues at positions R4 and R6 of the pyrimidine core but most importantly the prominent role to the unprecedented A1AR selectivity profile exerted by the Me group introduced at the exocyclic amino group. The structure-activity relationship trends on both A1 and A2AARs were conveniently interpreted with rigorous free energy perturbation simulations, which started from the receptor-driven docking model that guided the design of these series.

Journal of Medicinal Chemistry published new progress about Adenosine A1 receptor antagonists. 21667-62-9 belongs to class nitriles-buliding-blocks, and the molecular formula is C9H6ClNO, Quality Control of 21667-62-9 .

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Abel-Snape, Xavier; Wycich, Gina; Lautens, Mark published the artcile< Synthesis of Indenes and Benzofulvenes via a Palladium-Catalyzed Three-Component Reaction>, Category: nitriles-buliding-blocks, the main research area is indene benzofulvene preparation palladium catalyst three component reaction.

A palladium-catalyzed three-component domino reaction to access indene derivatives is reported. This reaction proceeds via the sequential formation of three bonds: the first two resulting from inter- and intramol. carbopalladation and the final bond arising from an attack by a terminating nucleophilic reagent. Modifying the starting tether on the iodoarene led to either indenes or benzofulvenes. Three termination variations were compatible with this sequence, which furnished products in moderate to good yields. The oxabicycle used in this work acts as an acetylene surrogate, which is revealed in a postcatalytic retro-Diels-Alder step. A diastereomerically enriched mixture of oxabicyclic derivatives allowed for preliminary results for the enantioselective synthesis of indenes.

ACS Catalysis published new progress about Alkenynes Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 38487-85-3 belongs to class nitriles-buliding-blocks, and the molecular formula is C8H8N2O, Category: nitriles-buliding-blocks.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Song, Jian; Zheng, Wen-Hua published the artcile< A highly enantioselective approach towards optically active γ-amino alcohols by tin-catalyzed kinetic resolution of 1,3-amino alcohols>, Computed Properties of 21667-62-9, the main research area is benzoyl amino alc preparation enantioselective tin; amino alc benzyl chloride acylation kinetic resolution.

A highly enantioselective kinetic resolution of racemic 1,3-amino alcs. via O-acylation was achieved using a chiral organotin as the catalyst. Alkyl- and aryl-substituted 1,3-amino alcs. were resolved with excellent efficiencies to afford the recovered 1,3-amino alcs. and acylative products with high enantioselectivities, with s factors up to >600. Notably, the chiral organotin catalyst was more selective for anti-1,3-amino alcs. than for syn-isomers. A Gram-scale reaction with loading using 2 mol% catalysts demonstrated the utility of this protocol.

Chemical Communications (Cambridge, United Kingdom) published new progress about Acylation. 21667-62-9 belongs to class nitriles-buliding-blocks, and the molecular formula is C9H6ClNO, Computed Properties of 21667-62-9.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Wan, Bin; Lu, Zhuoer; Wu, Zhuo; Cheng, Cang; Zhang, Yanghui published the artcile< Diastereoselective Construction of Eight-Membered Carbocycles through Palladium-Catalyzed C(sp3)-H Functionalization>, COA of Formula: C8H5BrFN, the main research area is alkylphenyl bromide biphenylene palladium catalyst diastereoselective cross coupling reaction; dihydrotribenzoannulene preparation.

A palladium-catalyzed cross-coupling reaction of 2-alkylphenyl bromides with biphenylene was developed. The reactions formed eight-membered carbocycles through C(sp3)-H activation and the formation of two C-C bonds, and the chiral products were obtained with excellent diastereoselectivity. The reaction provided a new strategy for the construction of eight-membered carbocycles, and the products represent a novel type of chiral scaffold.

Organic Letters published new progress about Aryl bromides Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 886761-96-2 belongs to class nitriles-buliding-blocks, and the molecular formula is C8H5BrFN, COA of Formula: C8H5BrFN.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Scheibler, Helmuth; Beiser, Willy; Cobler, Heinz; Schmidt, Anton published the artcile< Compounds of bivalent carbon. VIII. Some derivatives of diethoxyacetic acid and their adaptation to carbon monoxide acetal cleavage>, COA of Formula: C6H11NO2, the main research area is .

In the reaction between (EtO)2CHCO2Et and NaOEt or Et2NMgBr the C(OEt)2 formed by the cleavage of the C chain readily reacts with the EtOH which is split off simultaneously, forming pentaethoxyethane and heptaethoxypropane. Since the sec. NHEt2, is indifferent toward C(OEt)2, attempts were made to prepare dialkylamides of (EtO)2CHCO2H for use instead of (EtO)2CHCO2Et for the C(OEt)2 cleavage. These dialkylamides cannot be prepared under the usual conditions but (EtO)2CHCONMe2 (I) was finally obtained by heating the components in a sealed tube at 100° in the presence of CaCl2 to bind the EtOH set free, and (EtO)2CHCON(CH2Ph)2 (II) was obtained from (EtO)2CHCO2Et and (PhCH2)2NMgBr in boiling C6H6. When I and II were treated with Me2NMgBr and (PhCH2)2NMgBr, resp., and, after removal of the ether (both that used as solvent and the ether of constitution), the products were subjected to dry distillation in vacuo, the product obtained from Me2NMgBr yielded a compound m. 134° containing no trace of EtO (Zeisel) and giving NH3 instead of NHMe2 on hydrolysis. Analysis indicated that it was OHCCONH2.3H2O, and from the low-boiling products of the reaction (condensed in liquid air) was isolated Et2O after removal of the NHMe2 with C6H4(CO)2O in the presence of quinoline. In the experiment with II there was obtained no low-boiling distillate; the product was N(CH2Ph)3. formed according to the scheme (EtO)2CHC(OMgBr)[N(CH2Ph)2]2 → N(CH2Ph)3 + (EtO)2CHC(OMgBr):NCH2Ph. These dialkylamides are therefore not adapted to the C(OEt)2 cleavage. As (EtO)2CHCO2Et can be used for this purpose but the EtOH formed simultaneously gives rise to secondary reactions, attempts were made to prepare the Ph instead of the Et ester. (EtO)2CHCOCl cannot be made because 1 of the 2 EtO groups in (EtO)2CHCO2H immediately reacts with PCl5 or SOCl2. The Ph ester can be obtained by treating the acid in the presence of excess of pyridine first with SOCl2 and then with PhOH, but the. ester so prepared is difficultly purified. Favorable results were obtained only when ClSO2Ph was used with the acid in ether in the presence of pyridine, the resulting (EtO)2CHCOOSO2Ph decomposing on heating in ether into SO2 and (EtO)2CHCO2Ph. As the ester is very sensitive to acids it was freed from admixed pyridine with MeI. With Et2NMgBr the ester gave (EtO)2CHCONEt2 but the chief product was a non-distillable mass which decomposed at higher temperatures and was perhaps formed by combination of PhOH with a polymerization product of C(OEt)2. Furthermore, in the part of the product consisting chiefly of NHEt2, monomeric C(OEt)2 was detected and determined by means of HgCl2 after it had been hydrolyzed to HCO2H with dilute alkali. Diethoxyacetdimethylamide (I), b12 105°; yield, 50.5%. Dibenzylamide (II), light yellow, b1 168-70° (yield, 26%). Ph diethoxyacetate, b13 150-2°; yield, 61.1%. Diethoxyacetonitrile, obtained in 30% yield from the amide in quinoline slowly treated at 90° with P2O6, b12 55-6°.

Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen published new progress about 6136-93-2. 6136-93-2 belongs to class nitriles-buliding-blocks, and the molecular formula is C6H11NO2, COA of Formula: C6H11NO2.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Bowman, W. Russell; Bridge, Colin F.; Brookes, Philip; Cloonan, Martin O.; Leach, David C. published the artcile< Cascade radical synthesis of heteroarenes via iminyl radicals>, Computed Properties of 89324-17-4, the main research area is radical cyclization iminyl vinyl nitrile heteroarene preparation; heteroarene alkaloid tetracycle indolizinoquinolinone ring preparation; cyclization radical reaction mechanism iminyl.

A novel cascade cyclization protocol has been developed which ‘zips up’ two rings to form new tetracycles. In the protocol, treatment of vinyl bromides and iodides with hexamethylditin radicals yields intermediate vinyl radicals which undergo 5-exo cyclization onto nitrile groups to yield intermediate iminyl radicals. The iminyl radicals can undergo 6-endo cyclization (or 5-exo followed by neophyl rearrangement) to yield tetracyclic π-radicals which lose hydrogen radical in an H-abstraction step. Me radicals, generated from the breakdown of trimethylstannyl radicals, are proposed as a possible H-abstractor for this final oxidative step. The protocol has been used to synthesize the tetracyclic rings A-D (tetracycle indolizino[1,2-b]quinolin-9(11H)-one) of the anticancer alkaloids camptothecin, mappicine, nothapodytine B and nothapodytine A. The protocol has also been applied to the synthesis of analogs of camptothecin in which ring A has been replaced by thiophene (8,10-dihydrothieno[2′,3′:5,6]pyrido[2,3-a]indolizin-8-one) and ring D by pyrrole (10H-pyrrolizino[1,2-b]quinoline) and benzene (11H-indeno[1,2-b]quinolin-11-one).

Journal of the Chemical Society, Perkin Transactions 1 published new progress about Alkaloids Role: SPN (Synthetic Preparation), PREP (Preparation) (tetracyclic). 89324-17-4 belongs to class nitriles-buliding-blocks, and the molecular formula is C6H4N2O, Computed Properties of 89324-17-4.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Ben Messaouda, M.; Mahjoub, A.; Mogren Al-Mogren, M.; Abderrabba, M.; Hochlaf, M. published the artcile< Substituent effects on vibrational and electronic excitation spectra of pyridone tautomers and ions: The case of the cyano group>, Electric Literature of 89324-17-4, the main research area is substituent effect vibrational electronic excitation spectra cyano substituted pyridone.

In this theor. work, we computed the equilibrium geometries and a set of rotational and vibrational spectroscopic parameters for cyano substituted 2-pyridones neutral or cationic and their tautomers (cyano 2-hydroxypyridines). We examined also the effect of tautomerism equilibrium on those systems. In our anal., we mostly focused on the perturbations induced by the CN group on the electronic structure and on the spectroscopy of 2-pyridone/2-hydroxypyridine block. Moreover, we investigated the pattern of their low lying electronic states at both the PBE0/aug-cc-pVDZ D. Functional Theory (DFT) and the CASSCF/aug-cc-pVTZ levels of theory. Vertical excitation spectra and both adiabatic and vertical ionization energies were performed.

Journal of Molecular Structure published new progress about Adiabatic ionization potential. 89324-17-4 belongs to class nitriles-buliding-blocks, and the molecular formula is C6H4N2O, Electric Literature of 89324-17-4.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Jiang, Shuai; Cao, Wen-Bin; Xu, Xiao-Ping; Ji, Shun-Jun published the artcile< Cobalt-Catalyzed Isocyanide-Based Three-Component Cascade for the Synthesis of Quinazolines>, Related Products of 38487-85-3, the main research area is quinazoline preparation; arylisocyanide arylamine azide three component tandem heterocyclization cobalt catalyst.

A Co-catalyzed cyclization reaction of isocyanides 1-NC-4-R-5-R1C6H2CN (R = H, Me, F, OMe, etc.; R1 = H, OMe, Br), azides R2S(O)ON3 (R2 = n-Pr, Ph, cyclohexyl, thiophen-2-yl, etc.), and amines R3NH2 (R3 = n- Bu, Ph, 1-methyl-1H-indol-5-yl, etc.) to access quinazoline derivatives I and II (R4 = H, n-Bu, t-Bu, 4-methylphenyl) was described. This protocol features a high atom economy, mild reaction conditions, excellent yields, and a broad substrate scope. This cascade reaction involved three or four C-N bonds and the formation of one or two rings. The quinazolin-4(H)-imines I and II obtained are proven to be versatile intermediates for further valuable transformations. It was also found that the cobalt catalyst could be isolated from the reaction mixture and reused.

Organic Letters published new progress about Amines Role: RCT (Reactant), RACT (Reactant or Reagent). 38487-85-3 belongs to class nitriles-buliding-blocks, and the molecular formula is C8H8N2O, Related Products of 38487-85-3.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts