Tag: M.W=150-200

Yu, Shuling; Lv, Ningning; Liu, Zhanxiang; Zhang, Yuhong published the artcile< Cu(II)-Mediated C-C/C-O Bond Formation via C-H/C-C Bond Cleavage: Access to Benzofurans Using Amide as a Traceless Directing Group>, Safety of 3-(3-Chlorophenyl)-3-oxopropanenitrile, the main research area is benzofuran preparation; benzamide benzoylacetonitrile heterocyclization copper catalyst.

A copper-mediated synthesis of 2,3-disubstituted benzofurans I (R1 = H, 5-F, 3-Cl, 5-NO2, etc.; R2 = 4-MeC6H4, 4-FC6H4, 2-thienyl, etc.) with the assistance of an 8-aminoquinolyl auxiliary is described from readily available benzamides R1C6H4C(O)NHQ (Q=) and benzoylacetonitriles R2C6H4C(O)CH2CN. In this reaction, the C-C bond is successfully constructed via C-H activation, and C-O bond is subsequently formed at the original position of the amide group in a one-pot manner. The amide directing group is detached simultaneously under the reaction conditions through C-C bond cleavage. Surprisingly, the distinct isoquinolinone products II (R3 = H, 6-Me, 6-NO2, 7-CF3; R4 = H, Me) can be achieved by changing the reaction conditions using ammonia as amine source.

Advanced Synthesis & Catalysis published new progress about Acetonitriles Role: RCT (Reactant), RACT (Reactant or Reagent). 21667-62-9 belongs to class nitriles-buliding-blocks, and the molecular formula is C9H6ClNO, Safety of 3-(3-Chlorophenyl)-3-oxopropanenitrile.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Booth, Brian L.; Collis, Alan published the artcile< One-step synthesis of N1-(1-benzylisoquinolin-3-yl)phenylacetamidinium trifluoromethanesulfonate derivatives from phenylacetonitriles and trifluoromethanesulfonic acid>, COA of Formula: C8H5F2N, the main research area is phenylacetonitrile cyclotrimerization triflic acid; benzylisoquinolinylphenylacetamidinium triflate.

The phenylacetonitriles 3,4-R1R2C6H3CH2CN (I, R1 = H, Me, Cl, R2 = H; R1 = H, R2 = Cl, F; R1 = R2 = Cl, F) and 2-cyclohexylphenylacetonitrile react with CF3SO3H under various conditions to give the corresponding title salts, e.g. II, in moderate to high yields. This novel cyclotrimerization reaction can also be carried out with I (R1 = R2 = H) using FSO3H and, in low yield, with HBF4.Et2O while ClSO3H, 4-MeC6H4SO3H, and HCl/ZnCl2 give only PhCH2CONH2 under similar conditions. Reaction of I (R1 = R2 = H) with dry HCl resulted mainly in the formation of 1,3,5-tribenzyltriazine. Isoquinoline formation is not observed upon reaction of either I (R1 = H, MeO, R2 = MeO) with CF3SO3H, but complex product mixtures probably resulting from Houben-Hoesch reactions are obtained. I (R1 = H, R2 = AcO) gives a low yield of the Fries rearrangement product.

Journal of Chemical Research, Synopses published new progress about Cyclotrimerization. 658-99-1 belongs to class nitriles-buliding-blocks, and the molecular formula is C8H5F2N, COA of Formula: C8H5F2N.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Du, Bingnan; Jiang, Xiaoqing; Sun, Peipei published the artcile< Palladium-Catalyzed Highly Selective ortho-Halogenation (I, Br, Cl) of Arylnitriles via sp2 C-H Bond Activation Using Cyano as Directing Group [Erratum to document cited in CA158:330848]>, HPLC of Formula: 21423-84-7, the main research area is erratum halosuccinimide ortho halogenation arylnitrile palladium catalyst; nitrile aromatic ortho halogenation halosuccinimide palladium catalyst erratum.

The authors provide clarification that there is competition during the halogenation of 4-methoxybenzonitrile and revise the corresponding results.

Journal of Organic Chemistry published new progress about Halogenation catalysts. 21423-84-7 belongs to class nitriles-buliding-blocks, and the molecular formula is C8H6ClN, HPLC of Formula: 21423-84-7.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Porter, Thomas C.; Smalley, Robert K.; Teguiche, Mabrouk; Purwono, Bambang published the artcile< Tetrazolo[1,5-a]quinolines and 1,2,3-triazolo[1,5-a]quinazolines by the action of cyano carbanions on 2-azidoaryl carbonyl compounds>, Quality Control of 658-99-1, the main research area is tetrazoloquinoline preparation; quinoline tetrazolo preparation; triazoloquinazoline preparation; quinazoline triazolo preparation; cyano carbanion azidophenyl carbonyl compound cyclocondensation.

In protic solvents, 2-N3C6H4CHO undergoes base-catalyzed condensation with cyano carbanions to yield tetrazolo[1,5-a]quinolines, whereas in aprotic media 1,2,3-triazolo[1,5-a]quinazolines are formed. Triazoloquinazolines are also obtained from 2-N3C6H4Ac and from 2-N3C6H4CN, whereas with 2-N3C6H4COCl hydroxytetrazoloquinolines result. 2,1-Oxazolo[4,3-c]tetrazolo[1,5-a]quinolines are obtained by the action of selected cyano carbanions on 2-N3C6H4CN+O- and a 1,2,3-triazolo[1,5-a]quinoline by base-catalyzed condensation of 2-N3C6H4CN with (PhCH2)2CO.

Synthesis published new progress about Aromatic carbonyl compounds Role: RCT (Reactant), RACT (Reactant or Reagent). 658-99-1 belongs to class nitriles-buliding-blocks, and the molecular formula is C8H5F2N, Quality Control of 658-99-1.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Liu, Chong; Yuan, Jing; Zhang, Zhenfeng; Gridnev, Ilya D.; Zhang, Wanbin published the artcile< Asymmetric Hydroacylation Involving Alkene Isomerization for the Construction of C3-Chirogenic Center>, Name: 3-(3-Chlorophenyl)-3-oxopropanenitrile, the main research area is arylcyclopentanone enantioselective preparation; rhodium catalyst enantioselective intramol hydroacylation arylenal alkene isomerization; mechanism transition state energy rhodium catalyzed enantioselective hydroacylation arylenal; alkene isomerization; cycloketones; hydroacylation; rhodacycle; β-H elimination.

A new transformation pattern for enantioselective intramol. hydroacylation has been developed involving an alkene isomerization strategy. Proceeding through a five-membered rhodacycle intermediate, 3-enals such as I (or their Z isomers) were converted to C3- or C3,C5-chirogenic cyclopentanones such as II with satisfactory yields, diastereoselectivities, and enantioselectivities. A catalytic cycle has been theor. calculated and the origin of the stereoselection is rationally explained.

Angewandte Chemie, International Edition published new progress about Cyclopentanones Role: SPN (Synthetic Preparation), PREP (Preparation) (3-aryl-2,2-disubstituted). 21667-62-9 belongs to class nitriles-buliding-blocks, and the molecular formula is C9H6ClNO, Name: 3-(3-Chlorophenyl)-3-oxopropanenitrile.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Zeng, Ge; Liu, Jichao; Shao, Yinlin; Zhang, Fangjun; Chen, Zhongyan; Lv, Ningning; Chen, Jiuxi; Li, Renhao published the artcile< Selective Synthesis of β-Ketonitriles via Catalytic Carbopalladation of Dinitriles>, Computed Properties of 21667-62-9, the main research area is dinitrile arylboronic acid palladium carbopalladation addition catalyst; ketonitrile preparation.

A practical, convenient, and highly selective method of synthesizing β-ketonitriles from the Pd-catalyzed addition of organoboron reagents to dinitriles has been developed. This method provides excellent functional-group tolerance, a broad scope of substrates, and the convenience of using com. available substrates. The method is expected to show further utility in future synthetic procedures.

Journal of Organic Chemistry published new progress about Addition reaction. 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

Smith, William J. III; Sawyer, J. Scott published the artcile< A novel and selective method for the N-arylation of indoles mediated by KF/Al2O3>, HPLC of Formula: 94087-40-8, the main research area is regioselective arylation indole potassium fluoride.

Indole was treated with aryl electrophiles in the presence of 37% KF/Al2O3 and catalytic 18-crown-6 in DMSO at 120 °C to give regioselectively 1-arylindoles in fair to excellent yield. Electrophiles containing electronically unfavorable substitution patterns or leaving groups, such as 3-chlorobenzonitrile, coupled effectively under the reaction condition. For example, the potassium-fluoride mediated arylation of 1H-indole with 3-chloro-2-fluorobenzonitrile gave 3-chloro-2-(1H-indol-1-yl)benzonitrile (68% yield).

Tetrahedron Letters published new progress about Arylation, regioselective. 94087-40-8 belongs to class nitriles-buliding-blocks, and the molecular formula is C7H3ClFN, HPLC of Formula: 94087-40-8.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Sheng, Cheng; Ling, Zheng; Ahmad, Tanveer; Xie, Fang; Zhang, Wanbin published the artcile< Copper-Catalyzed Regioselective [3+3] Annulations of Alkynyl Ketimines with α-Cyano Ketones: the Synthesis of Polysubstituted 4H-Pyran Derivatives with a CF3-Containing Quaternary Center>, Application In Synthesis of 21667-62-9, the main research area is trifluoromethyl pyran preparation regioselective enantioselective; alkynyl ketimine cyano ketone ring closing reaction copper catalyst; [3+3] annulations; copper catalyzed; polysubstituted 4H-pyran derivatives.

Regioselective [3+3] annulation of alkynyl ketimines R1CCC(=NR)(CF3) (R1 = benzyl, naphthalen-1-yl, triethylsilyl, etc.; R = Boc) with α-cyano ketones R2C(O)CH2CN (R2 = Et, 4-methylphenyl, thiophen-2-yl, etc.) for the synthesis of polysubstituted 4H-pyran derivatives I with a quaternary CF3-containing center has been realized by using Cu(OAc)2 as the catalyst. The novel strategy tolerates a wide range of α-CF3 alkynyl ketimines and α-cyano ketones with both aryl and alkyl substituents. A preliminary asym. synthesis of chiral product II (R3 = Ph, 4-MeC6H4, 4-ClC6H4, etc.; R4 = Boc, Cbz) has been attempted by using copper and chiral thiourea as the cocatalyst with excellent yields (86-99%) and good enantioselectivities (71-78% ee). Furthermore, product I (R = Boc; R1 = R2 = Ph) could be obtained on a gram-scale reaction with 75% yield and 99% ee after recrystallization Several products were also transformed readily. Control experiments indicate that the reaction involves a process with a base-catalyzed or chiral thiourea-catalyzed Mannich-type reaction followed by a highly regioselective copper-catalyzed ring-closing reaction on the alkynyl moiety in a 6-endo-dig fashion.

Chemistry – A European Journal published new progress about [3+3] Cycloaddition reaction (regio-, stereoselective). 21667-62-9 belongs to class nitriles-buliding-blocks, and the molecular formula is C9H6ClNO, Application In Synthesis of 21667-62-9.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Gonzalez-Fernandez, Rebeca; Crochet, Pascale; Cadierno, Victorio published the artcile< Synthesis of β-hydroxyamides through ruthenium-catalyzed hydration/transfer hydrogenation of β-ketonitriles in water: Scope and limitations>, Category: nitriles-buliding-blocks, the main research area is ketonitrile preparation ruthenium catalyst tandem hydration transfer hydrogenation; hydroxyamide preparation.

A cascade process for the straightforward one-pot conversion of β-ketonitriles into β-hydroxyamides was reported. The process, that proceeded in water employing the arene-ruthenium(II) complex [RuCl2(η6-p-cymene){P(4-C6H4F)2Cl}] as catalyst in combination with sodium formate involved the initial hydration of the β-ketonitrile substrates to generate the corresponding β-ketoamide intermediates which subsequently undergo the transfer hydrogenation (TH) of the carbonyl group. Employing a family of forty different β-ketonitriles featuring diverse substitution patterns, the scope and limitations of the processed was established.

Journal of Organometallic Chemistry published new progress about Amides, hydroxy Role: SPN (Synthetic Preparation), PREP (Preparation). 21667-62-9 belongs to class nitriles-buliding-blocks, and the molecular formula is C9H6ClNO, Category: nitriles-buliding-blocks.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Tan, Xiangyu; Gu, Qianqian; Yang, Xingjiang; Yang, Yingying; Hu, Bingwei; Mao, Shuai; Lin, Jun; Jin, Yi published the artcile< Palladium-Catalyzed [2+3] Cycloaddition/Cross-Coupling Reaction: Z/E and Diastereoselective Synthesis of Dendralene-Functionalized Dihydrofurans>, Name: 3-(3-Chlorophenyl)-3-oxopropanenitrile, the main research area is dendralene dihydrofuran preparation diastereoselective; allenyl acetate oxonitrile cycloaddition cross coupling palladium catalyst.

Herein, a Pd-catalyzed [2+3] cycloaddition/cross-coupling reaction of allenyl acetates R(OAc)CH=C=CH2 (R = Ph, 4-phenylphenyl, naphthalen-1-yl, thiophen-3-yl, etc.) for the Z/E selective and diastereoselective synthesis of dendralene-functionalized dihydrofurans I (R1 = Ph, 4-fluorophenyl, cyclopropyl, furan-2-yl, etc.) were described. Remarkably, mechanistic studies show the formation of an epoxide from a carbonyl bond via cycloaddition, which is practically and mechanistically significant for the construction of other bioactive heterocyclic epoxides. This research also revealed the utility and potential of allenic esters as C2 synthons and 1,2-biselectrophiles in cycloaddition reactions.

Organic Letters published new progress about [3+2] Cycloaddition reaction. 21667-62-9 belongs to class nitriles-buliding-blocks, and the molecular formula is C9H6ClNO, Name: 3-(3-Chlorophenyl)-3-oxopropanenitrile.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts