Month: October 2022

Guo, Wei; Cai, Liuhuan; Xie, Zhen; Mei, Weijie; Liu, Gongping; Deng, Ling; Zhuo, Xiaoya; Zhong, Yumei; Zou, Xiaoying; Zheng, Lvyin; Fan, Xiaolin published the artcile< Photocatalyzed intermolecular amination for the synthesis of hydrazonamides>, Computed Properties of 21667-62-9 , the main research area is hydrazonamide preparation diastereoselective; ketonitrile disubstituted hydrazine amination photocatalyst.

A sequential multi-component reaction of β-ketonitriles with N,N-disubstituted hydrazines is designed and developed through a photocatalyzed intermol. amination process to afford hydrazonamides I [R = Et, Ph, 2-furyl, etc.; R1 = Me, Et, n-Pr, etc.; R2 = Ph, 3-MeC6H4, 4-ClC6H4, etc.]. This work reported the first example of the use of N,N-disubstituted hydrazines as two different “”amine”” sources, characterized by isotope labeling experiments The C-CN/N-N bonds were cleaved and new C-N/C=N bonds were constructed in a one-pot reaction. This protocol could be carried out without the addition of any external metals, ligands, bases, oxidants and reductants, and possessed the advantages of operational simplicity, mild reaction conditions, and good functional group tolerance. Furthermore, this approach enabled late-stage modifications of structurally complex bioactive mols., natural products and drugs, thus showing potential applications in the field of organo-pharmaceutical chem.

Organic Chemistry Frontiers published new progress about Amination. 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

Bollini, Mariela; Domaoal, Robert A.; Thakur, Vinay V.; Gallardo-Macias, Ricardo; Spasov, Krasimir A.; Anderson, Karen S.; Jorgensen, William L. published the artcile< Computationally-Guided Optimization of a Docking Hit to Yield Catechol Diethers as Potent Anti-HIV Agents>, Product Details of C7H3ClFN, the main research area is catechol ether anti HIV reverse transcriptase inhibitor computational optimization.

A 5-μM docking hit has been optimized to an extraordinarily potent (55 pM) non-nucleoside inhibitor of HIV reverse transcriptase. Use of free energy perturbation (FEP) calculations to predict relative free energies of binding aided the optimizations by identifying optimal substitution patterns for Ph rings and a linker. The most potent resultant catechol diethers feature terminal uracil and cyanovinylphenyl groups. A halogen bond with Pro95 likely contributes to the extreme potency of compound 42 (I). In addition, several examples are provided illustrating failures of attempted grafting of a substructure from a very active compound onto a seemingly related scaffold to improve its activity.

Journal of Medicinal Chemistry published new progress about AIDS (disease). 94087-40-8 belongs to class nitriles-buliding-blocks, and the molecular formula is C7H3ClFN, Product Details of C7H3ClFN.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Shiba, Tetsuo; Inami, Kaoru; Sawada, Kozo; Hirotsu, Yoshihiro published the artcile< Synthesis and geometric configuration of 2-(hydroxyiminomethyl)thiazole-4-carboxylic acid in antibiotic althiomycin>, Application of C6H11NO2, the main research area is althiomycin configuration; hydroxyiminomethylthiazole preparation configuration.

Isomeric oximes I (R = Et) were prepared from (EtO)2CHCO2Et in 6 steps. The isomers were separated and their configuration determined by nuclear Overhauser enhancement. These assignments were used to established that I (R = H) in althiomycin have the syn configuration and it isomerized on purification on acid ion exchange resin. Althiomycin has the syn configuration II.

Heterocycles published new progress about Configuration. 6136-93-2 belongs to class nitriles-buliding-blocks, and the molecular formula is C6H11NO2, Application of C6H11NO2.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Balwe, Sandip Gangadhar; Kim, Jong Su; Kim, Yeong-Il; Jeong, Yeon Tae published the artcile< Diversity-oriented one-pot synthesis of furan based densely substituted biheteroaryls via isocyanide insertion>, Category: nitriles-buliding-blocks, the main research area is aroylacetonitrile arylglyoxal Knoevenagel condensation isocyanide insertion cascade heterocyclization; biheteroaryl furan diversity oriented synthesis; PTSA Knoevenagel condensation isocyanide insertion cascade heterocyclization catalyst.

A facile and efficient acid-catalyzed cascade reaction for the synthesis of novel biheteroaryl structural motifs containing densely functionalized furans has been developed. The reaction sequence involves a Knoevenagel condensation of arylglyoxals with aroyl or heteroaroylacetonitrile and subsequently an isocyanide insertion via formal [4+1] cycloaddition followed by rapid [1,3]-H shift to afford uniquely decorated novel biheterocycles, e.g., I. Furthermore, the scope of the methodol. was extended to diverse biheteroaryls by employing 3-(2-furyl)-3-oxopropanenitrile, 3-cyanoacetyl-1-methylindole, 3-oxo-3-(1H-pyrrol-2-yl)propanenitrile, 3-(1H-indol-3-yl)-3-oxopropanenitrile, 3-oxo-3-(2-thienyl)propionitrile and benzoylacetonitriles.

Tetrahedron published new progress about [4+1] Cycloaddition reaction (formal). 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

Yadav, Maruti B.; Vagh, Sandip S.; Jeong, Yeon Tae published the artcile< Divergent Annulation of Spiro[indoline-pyran] and Fused (Epoxyetheno)indeno-Furan from 1,2-Diketone and 1-Cyanoketone>, Formula: C9H6ClNO, the main research area is isatin benzoylacetonitrile base catalyst regioselective chemoselective Paal Knorr reaction; benzoylphenyl oxospiroindolinepyran carbonitrile preparation; acenaphthylenedione benzoylacetonitrile base catalyst regioselective chemoselective Paal Knorr reaction; epoxyethenoindeno furancarbonitrile preparation.

A simple and efficient method for the construction of spiro[indoline-pyran] and fused (epoxyetheno)indeno[1,2-b]furan compounds from 1-cyanoketones and 1,2-diketone was developed. The synthesis proceeded via the Knoevenagel and Michael adduct through intramol./Paal-Knorr cyclization under similar reaction condition. The less commonly used 1-cyanoketones and active carbonyl compounds served as the indole containing pyran and bicyclic furan source for the preparation of a new series of heterocyclic compounds This heterocyclic structure allows one and more than one tetra-substituted carbon center and sequential hexa- and penta-cyclic core under very mild conditions and showed excellent chemo and regioselectivity. In addition, the synthesis of spiro[indoline-pyran] and (epoxyetheno)indeno[1,2-b]furan was demonstrated in a gram scale.

European Journal of Organic Chemistry published new progress about Chemoselectivity. 21667-62-9 belongs to class nitriles-buliding-blocks, and the molecular formula is C9H6ClNO, Formula: C9H6ClNO.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Burkholder, Timothy P.; Kudlacz, Elizabeth M.; Maynard, George D.; Liu, Xiao-Gao; Le, Tieu-Binh; Webster, Mark E.; Horgan, Stephen W.; Wenstrup, David L.; Freund, David W.; Boyer, Fred; Bratton, Larry; Gross, Raymond S.; Knippenberg, Robert W.; Logan, Deborah E.; Jones, Bryan K.; Chen, Teng-Man; Geary, Julie L.; Correll, Melinda A.; Poole, J. Chuck; Mandagere, Arun K.; Thompson, Thomas N.; Hwang, Kin-Kai published the artcile< Synthesis and structure-activity relationships for a series of substituted pyrrolidine NK1/NK2 receptor antagonists>, Category: nitriles-buliding-blocks, the main research area is pyrrolidine preparation neurokinin receptor antagonist; structure activity pyrrolidine neurokinin receptor antagonist.

The authors recently described the synthesis and characterization of MDL 105,212, a non peptide tachykinin antagonist with high affinity for NK1 and NK2 receptors. Here, the authors report the synthesis and structure-activity relationships for a series of analogs of MDL 105,212, I (Ar1 = 3-ClC6H4, 4-FC6H4, 3-pyridyl, etc., Ar2 = Ph, 3-MeOC6H4, 4-FC6H4, 3-, 4-pyridyl, R1R2N, = H2N, piperidino, morpholino, 4-methylpiperidino) and II (Ar2 = Ph, 3-, 4-pyridyl, R1R2N = H2N, morpholino, 4-methylpiperidino), with regards to NK1 and NK2 receptor binding affinity, phys.-chem. characterization; in vitro absorption potential; in vitro metabolic stability; and efficacy in a capsaicin-challenge conscious guinea pig model after oral administration.

Bioorganic & Medicinal Chemistry Letters published new progress about Structure-activity relationship, neurokinin receptor-binding. 658-99-1 belongs to class nitriles-buliding-blocks, and the molecular formula is C8H5F2N, Category: nitriles-buliding-blocks.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Gore, Babasaheb Sopan; Chiang, Chun-Hsien; Lee, Chein Chung; Shih, Yi-Lun; Wang, Jeh-Jeng published the artcile< De Novo Protocol for the Construction of Benzo[a]fluorenes via Nitrile/Alkene Activation>, Recommanded Product: 3-(3-Chlorophenyl)-3-oxopropanenitrile, the main research area is nitrile alkene alkyne chemoselective regioselective annulative cyclodimerization; benzofluorene preparation.

Unprecedented chemo- and regioselective synthesis of benzo[a]fluorenes and naphthamide-substituted benzo[a]fluorenes were constructed from the reaction of (E)-2-aroyl-3-(2-(arylalkynes/alkenes)aryl)acrylonitrile scaffolds under metal-free conditions via the activation of nitriles and alkenes, resp. A tentative reaction mechanism was proposed for this homofunctionalization of nitriles. Control experiments showed that the reaction proceeds via selective nitrile or alkene protonation, depending upon the substrates. Addnl., we demonstrated an alternative expeditious route for the synthesis of disubstituted benzo[a]fluorenes in the presence of TfOH alone.

Organic Letters published new progress about Alkenes Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 21667-62-9 belongs to class nitriles-buliding-blocks, and the molecular formula is C9H6ClNO, Recommanded Product: 3-(3-Chlorophenyl)-3-oxopropanenitrile.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Mondal, Buddhadeb; Balha, Megha; Pan, Subhas Chandra published the artcile< Organocatalytic asymmetric spirocyclization reactions of cyclic 2,4-dienones with cyanoketones: synthesis of spiro-dihydropyrano cyclohexanones>, Application In Synthesis of 21667-62-9 , the main research area is cyclic dienone cyanoketone cinchona alkaloid organocatalyst spirocyclization; spiro dihydropyrano cyclohexanone diastereoselective enantioselective preparation.

The first organocatalytic asym. synthesis of spiro-dihydropyrano cyclohexanones was developed via the cascade reaction between cyanoketones and cyclic 2,4-dienones. A cinchona alkaloid-derived bifunctional primary amine catalyst in combination with N-Boc-tleucine was found to be the most effective for this spirocyclization reaction and provided the desired products in moderate to good yields with high enantioselectivities.

Organic & Biomolecular Chemistry published new progress about Alkadienones Role: PRP (Properties), RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 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

Liu, Hui; Yan, Yingkun; Zhang, Jiayan; Liu, Min; Cheng, Shaobing; Wang, Zhouyu; Zhang, Xiaomei published the artcile< Enantioselective dearomative [3+2] annulation of 5-amino-isoxazoles with quinone monoimines>, Synthetic Route of 21667-62-9, the main research area is aminoisoxazole quinone monoimine chiral phosphoric acid catalyst dearomative cycloaddition; benzofuroisoxazole diamine preparation enantioselective; quinone monimine aminoisoxazole phosphoric acid tandem dearomative cycloaddition cyclization; epoxyazenometheno dihydrobenzofuropyrrolyl benzenesulfonamide preparation enantioselective.

The first enantioselective dearomative [3+2] annulation of 5-aminoisoxazoles with quinone monoimines was realized using a chiral phosphoric acid as catalyst. Various novel (bridged) isoxazoline fused dihydrobenzofurans bearing two continuous quaternary stereocenters were achieved in moderate to good yields (up to 94%) with moderate to good enantioselectivities (up to 98% ee). The absolute configurations of two products were assigned by X-ray crystal structural analyses and a plausible reaction mechanism was proposed.

Chemical Communications (Cambridge, United Kingdom) published new progress about [3+2] Cycloaddition reaction catalysts (dearomative, stereoselective). 21667-62-9 belongs to class nitriles-buliding-blocks, and the molecular formula is C9H6ClNO, Synthetic Route of 21667-62-9.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Yadav, Maruti B.; Bhosle, Suresh R.; Jeong, Yeon Tae published the artcile< DBU-promoted synthesis of novel heterocyclic [4.3.3] propellanes from α-cyanoketones and cyclic α-diketones>, Related Products of 21667-62-9, the main research area is heterocyclic tetrahydro benzofuran propellane preparation chemoselective diastereoselective one pot; cyclic alpha diketone cyanoketone multicomponent DBU catalyst.

An effective base-catalyzed Knoevenagel, Michael and intramol./Paal-Knorr cyclization strategy for the construction of heterocyclic [4.3.3] tetrahydro epoxyetheno benzo-furan propellanes (TEBFs) from cyclic α-diketones and α-cyanoketones is reported through single-step reaction. The reaction proceeds under mild reaction conditions and shows excellent chemo and diastereoselectivity in the absence of any external transition metal and ligands. The one-pot two-component procedure also shows the merits of straightforward reaction conditions, simple operation, using available feedstock, wide substrate scope, and high atom and step economy. This reaction provides facile access to highly substituted fused tetrahydro furo-furan propellanes, which can be used in the field of chem. and pharmaceutical research.

Tetrahedron Letters published new progress about Aryl ketones Role: RCT (Reactant), RACT (Reactant or Reagent) (cyano). 21667-62-9 belongs to class nitriles-buliding-blocks, and the molecular formula is C9H6ClNO, Related Products of 21667-62-9.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts