Month: October 2022

Traboulsi, Iman; Dange, Nitin S.; Pirenne, Vincent; Robert, Frederic; Landais, Yannick published the artcile< Enantioselective Total Synthesis of (+)-Eucophylline>, HPLC of Formula: 38487-85-3, the main research area is eucophylline total enantioselective synthesis free radical cyanation; Eucophylline; Monoterpene indole Alkaloid; cyclobutane; cyclobutene; cyclopropane; radical; sulfonyl-cyanation.

The total enantioselective synthesis of (+)-eucophylline (I) was achieved using as a key-structural motif a chiral piperidinone, II, bearing the natural product all-carbon quaternary stereocenter. The elaboration of the latter is based on two strategies relying on the free-radical carbo-cyanation and sulfonyl-cyanation resp. of enantiopure substituted cyclopropenes and cyclobutenes. Co- or Ni-boride reduction of the nitrile functional group along with the cyclopropane and cyclobutane ring-opening then led to the formation of the chiral piperidinone ring. Further elaboration of the latter into the key 1-azabicyclo[3.3.1]nonane motif followed by its coupling with a 2-cyanoaniline allowed the formation of the tetrahydrobenzo[b][1,8]-naphthyridine skeleton of I, which was finally accessible in 17 steps and 5.9% overall yield from 1,1-dibromobutene.

Chemistry – A European Journal published new progress about Cyanation. 38487-85-3 belongs to class nitriles-buliding-blocks, and the molecular formula is C8H8N2O, HPLC of Formula: 38487-85-3.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Kalogirou, Andreas S.; Kourtellaris, Andreas; Koutentis, Panayiotis A. published the artcile< Synthesis and Reactivity of 3',5'-Dichloro-1H-spiro(quinazoline-2,4'-[1,2,6]thiadiazin)-4(3H)-ones>, Quality Control of 38487-85-3, the main research area is chloro spiro quinazoline thiadiazine derivative synthesis reactivity.

A three-step synthesis of 3′,5′-dichloro-1H-spiro(quinazoline-2,4′-[1,2,6]thiadiazin)-4(3H)-ones starting from 3,4,4,5-tetra-chloro-4H-1,2,6-thiadiazine (I) is presented. The latter reacts with 2-aminobenzonitriles to give 2-[(3,5-dichloro-4H-1,2,6-thiadiazin-4-ylidene)amino]benzonitriles [e.g., I + 2-aminobenzonitrile → II (86%)] , which affords, after hydration, the resp. benzamides [II → III (84%)]. Upon heating at reflux in EtOH or HFIP, the benzamides intramolecularly cyclize onto the thiadiazine C4 position to give 3′,5′-dichloro-1H-spiro(quinazoline-2,4′-[1,2,6]thiadiazin)-4(3H)-ones [III → IV (95% in EtOH, 97% in HFIP)]. Single crystal X-ray crystallog. supports the structure of two analogs. The chloride displacement of these new spiroquinazolinones was demonstrated by Stille coupling, and by reaction with methoxide to afford both the mono and bis-methoxy derivatives

European Journal of Organic Chemistry published new progress about Aromatic nitriles Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation) (anthranilonitriles → [(dichlorothiadiazinylidene)amino]benzonitriles). 38487-85-3 belongs to class nitriles-buliding-blocks, and the molecular formula is C8H8N2O, Quality Control of 38487-85-3.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Bochis, Richard J.; Chabala, John C.; Harris, Ellwood; Peterson, Louis H.; Barash, Louis; Beattie, Thomas; Brown, Jeannette E.; Graham, Donald W.; Waksmunski, Frank S. published the artcile< Benzylated 1,2,3-triazoles as anticoccidiostats>, Recommanded Product: 2-Chloro-4-methylbenzonitrile, the main research area is triazole benzylated preparation anticoccidiostat; carbamoylaminotriazole preparation anticoccidiostat; structure activity carbamoylaminotriazole anticoccidiostat; aminobenzylcarbamoyltriazole preparation anticoccidiostat; benzyltriazole aminocarbamoyl preparation anticoccidiostat.

Substituted aminocarbamoyltriazoles I (R = Cl, H, COC6H4Cl-4; R1 = COC6H4R3, COPh, H, Cl, R3 = 4-Cl, 4-F, 4-cyano, 4-CO2Me, 4-CCl:CCl2, 4-Br, 4-iodo; R1 = COC6H3Cl2-3,4, COC6H3Cl2-2,6, etc.; R2 = H, Cl, F, Br) were prepared and evaluated in vivo for anticoccidial activity. Thus, N-alkylation of 5-amino-4-carbamoyl-1,2,3-triazole with benzene derivatives II (R4 = Br) gave I. Cyclization of II (R4 = N3) with 2-cyanoacetamide also gave I. I (R = R2 = Cl, R1 = COC6H4Cl-4) is a highly effective coccidiostat. An increase in activity was observed when the CO of the benzophenone moiety is flanked by halogens as in I (R = R2 = Cl, R1 = COC6H4Cl-4; R = R2 = Cl, R1 = COPh).

Journal of Medicinal Chemistry published new progress about Coccidiostats. 21423-84-7 belongs to class nitriles-buliding-blocks, and the molecular formula is C8H6ClN, Recommanded Product: 2-Chloro-4-methylbenzonitrile.

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>, Computed Properties of 21667-62-9 , 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, Computed Properties of 21667-62-9 .

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Suzuki, Itaru; Ogura, Kazuki; Shimazu, Jun-ya; Shibata, Ikuya published the artcile< Magnesium Halide-Catalyzed Synthesis of Oxaspiro[2.5]octenes from a Methylenecyclopropane and Acyl Cyanoalkenes>, COA of Formula: C9H6ClNO, the main research area is oxaspirooctene preparation diastereoselective chemoselective; methylenecyclopropane acyl cyanoalkene cyclization magnesium halide catalyst.

MgX2-catalyzed annulation of 1,1-di-Et 2-methylidenecyclopropane-1,1-dicarboxylate with acyl cyanoalkenes RC(O)C(CN)=CHAr (R = Me, Ph, 3-chlorophenyl, etc.; Ar = 4-fluorophenyl, 1-naphthyl, 2-furyl, etc.) was accomplished to give oxaspiro[2.5]octenes I (E = C(O)OEt) and II in excellent yields. The reaction proceeded through a rare intramol. oxa-Michael addition of Mg enolate. The oxaspiro ring was transformed into di-Et 2-((5-cyano-4,6-diphenyl-4H-pyran-2-yl)methyl)malonate at a higher temperature in the presence of MgX2.

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, COA of Formula: C9H6ClNO.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Clark, Robin D.; Jahangir, Alam published the artcile< Lateral lithiation reactions promoted by heteroatomic substituents>, Recommanded Product: 2,2-Diethoxyacetonitrile, the main research area is review Reactions; review Promoted; review Heteroatomic; review Substituents; review Lithiation; review Lateral.

A review of the article Lateral lithiation reactions promoted by heteroat. substituents.

Organic Reactions (Hoboken, NJ, United States) published new progress about Organic synthesis. 6136-93-2 belongs to class nitriles-buliding-blocks, and the molecular formula is C6H11NO2, Recommanded Product: 2,2-Diethoxyacetonitrile.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Aldeborgh, Hannah; George, Kaylene; Howe, Morgan; Lowman, Heili; Moustakas, Holger; Strunsky, Nora; Tanski, Joseph M. published the artcile< Analysis of Small Molecule X-Ray Crystal Structures: Chemical Crystallography with Undergraduate Students in a Teaching Laboratory>, COA of Formula: C7H3ClFN, the main research area is mol xray crystal structure crystalline chem education analysis.

Abstract: The mol. structures of six small mol. organic compounds have been studied by X-ray diffraction in collaboration with undergraduate students enrolled in an advanced integrated laboratory course. The structures of 3-chloro-2-fluorobenzonitrile (1) [orthorhombic, P212121, a = 3.7679(13) Å, b = 12.546(4) Å, c = 13.780(5) Å], 5-chloro-2-fluorobenzonitrile (2) [monoclinic, P21/c, a = 3.7909(7) Å, b = 14.265(3) Å, c = 12.171(2) Å, β = 92.314(3)°], 2-bromo-3′-hydroxyacetophenone (3) [triclinic, P-1, a = 7.7081(3) Å, b = 9.8840(3) Å, c = 10.7320(4) Å, α = 98.4345(4)°, β = 90.6184(4)°, γ = 105.9259(4)°], 3-chlorobenzoylacetonitrile (4) [monoclinic, Cc, a = 4.8086(6) Å, b = 32.929(4) Å, c = 10.5855(13) Å, β = 97.665(1)°], 4-bromo-1-indanone (5) [triclinic, P-1, a = 7.3731(4) Å, b = 7.5419(4) Å, c = 8.2370(4) Å, α = 62.927(1)°, β = 71.160(1)°, γ = 71.521(1)°], and 4-bromo-1-indanol (6) [monoclinic, P21/c, a = 12.7914(9) Å, b = 4.6949(4) Å, c = 27.864(2) Å, β = 94.707(1)°] reveal several different types of intermol. interactions, such as hydrogen bonding, π-stacking, halogen-halogen interactions, and C-H···X (X = O, N, halogen) interactions. Graphical Abstract: The mol. structures of six small mol. organic compounds have been studied by X-ray diffraction in collaboration with undergraduate students enrolled in an advanced integrated laboratory course. The structures reveal several different types of intermol. interactions, such as hydrogen bonding, π-stacking, halogen-halogen interactions, and C-H···X (X = O, N, halogen) interactions.

Journal of Chemical Crystallography published new progress about Chemical education (undergraduate, organic). 94087-40-8 belongs to class nitriles-buliding-blocks, and the molecular formula is C7H3ClFN, COA of Formula: C7H3ClFN.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

McElvain, S. M.; Clarke, Robert L. published the artcile< Ketene acetals. XVIII. Pentaethoxyethane and tetraethoxyethylene (diethoxyketene diethyl acetal)>, Recommanded Product: 2,2-Diethoxyacetonitrile, the main research area is .

Because Scheibler (C.A. 20, 2824) has reported that tetraethoxyethylene (diethoxyketene di-Et acetal) (I) dissociate spontaneously into C(OEt)2, an unequivocal synthesis of I was desirable. (EtO)2CHCO2Et (II) yields 84% (EtO)2CHCONH2 (III) and this with Et3N gives 76-9% (EtO)2CHCN (IV). By the method of M. and Nelson (C.A. 36, 5772.3) IV yields 66-71% (EtO)2CHC(OEt):NH2Cl (V); addition of 23.3 g. V to 30.6 g. K2CO3 in 40 ml. H2O (covered with 60 ml. ether) at -5° and shaking 1 min. give 80% Et diethoxyacetimidate (VI), b20 91-2°, nD25 1.4147, d425 0.957. VI (47.5 g.) and 104 g. absolute EtOH, kept 4 days at room temperature, give 42% NH4Cl; the remainder of the N was recovered as III; when the alc. solution was distilled, the only products isolated were a small quantity of ether and 26% II; however, if the alc. filtrate was made alk. (to phenolphthalein) with EtONa before heat was applied, there were formed 8% II, 44% III, 8% V, and 12% Et diethoxyorthoacetate (pentaethoxyethane) (VII), b8 85-6°, b. 205-7°, nD25 1.4072, d425 0.935. VII (4.7 g.), added (10 min.) to 0.08 mole EtNa in petr. ether in a N atm., gives 39% I, b5 70-1°, b740 195-6°, nD25 1.4213, d425 0.949; it shows no tendency to dissociate With EtOH I gives VII; with Br it yields (CO2Et)2 and, presumably, EtBr. (CONH2)2 m. 350° (decomposition, Cu block) or decompose 340° in a sealed tube; Michael (Ber. 28, 1632 (1895)) reported a m.p. of 417-19° (decomposition).

Journal of the American Chemical Society published new progress about 6136-93-2. 6136-93-2 belongs to class nitriles-buliding-blocks, and the molecular formula is C6H11NO2, Recommanded Product: 2,2-Diethoxyacetonitrile.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Zhang, Ya-Kai; Wang, Bin published the artcile< Synthesis of α-Ketoamides from β-Ketonitriles and Primary Amines: A Catalyst-Free Oxidative Decyanation-Amidation Reaction>, Reference of 21667-62-9 , the main research area is ketoamide preparation; ketonitrile amine decyanation amidation.

AN oxidative decyanation-amidation of β-ketonitriles and primary amines readily occurs using hydrogen peroxide sodium carbonate adduct (Na2CO3·1.5H2O2), K2CO3, and 1,4-dioxane. This reaction affords α-ketoamides under mild conditions without the need of a catalyst.

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

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>, Computed Properties 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, Computed Properties of 21667-62-9 .

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts