Tag: M.W=100-150

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

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

Dulou, Raymond; Savostianoff, Dimitri published the artcile< Synthesis of glyoxal acetals from diethoxyacetonitrile>, Computed Properties of 6136-93-2, the main research area is .

A series of RCOCH(OEt)2 (I) was prepared from (EtO)2CHCN (II) with the corresponding RMgX. II was obtained in 77% yield by ammonolysis of (EtO)2CHCO2Et and subsequent dehydration of the resulting (EtO)2CHCONH2. II (12.9 g.) in 150 cc. dry Et2O added to about 0.2 mol appropriate RMgX in Et2O (1-1.9 mol/kg.), stirred 1 h., kept 12 h. at room temperature, treated with 50 g. NH4Cl in 200 cc. H2O, and acidified with concentrated HCl to pH 2-3 yielded 80-95% corresponding I listed in the table. R, b.p./mm., n20D, d2020, % yield; Et, 98-100°/55, 1.408, 0.929, 80; iso-Pr, 103-4°/45, 1.408, 0.910, 79; Am, 104-7°/9, 1.420, 0.913, 94; C7H15, 126-30°/10-11, 1.426, 0.886, 94; Ph, 135-6°/12, 1.505, 1.040, 80; cyclohexyl, 108-13°/10, 1.448, 0.961, 95;

Comptes Rendus des Seances de l’Academie des Sciences, Serie C: Sciences Chimiques published new progress about 6136-93-2. 6136-93-2 belongs to class nitriles-buliding-blocks, and the molecular formula is C6H11NO2, Computed Properties of 6136-93-2.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Kuzuya, Masayuki; Noguchi, Akihiro; Okuda, Takachiyo published the artcile< Quantum chemical consideration of substituent effects on tautomeric properties of 2-pyridones-2-pyridinols>, Reference of 89324-17-4, the main research area is tautomerism pyridone pyridinol UV; MO tautomerism pyridone; substituent effect pyridone tautomerism.

The tautomeric properties of 2-pyridones-2-pyridinols exerted by the substituent effect were discussed on the basis of quantum chem. quantities deduced from MO calculations A substituent at the 6-position has the greatest stabilizing effect. The magnitude of this effect was greater on the 2-pyridinol form than on the 2-pyridone form, irresp. of the nature of the substituent. This led to a large predominance of the 2-pyridinol form on the 6-polar-substituted derivatives, to such an extent that it was observed by conventional UV measurements at ambient temperature In the 6-Me derivative, the 2-pyridinol form was not observed by a similar measurement due to the weak substituent effect. The association ability is still an important factor in determining tautomeric equilibrium in a solution, resulting in a strong lability to the mol. environment. The substituent effects on the stabilities of both tautomers were correlated with the N-at. charges and ring structural modifications of the tautomers.

Bulletin of the Chemical Society of Japan published new progress about Electron configuration. 89324-17-4 belongs to class nitriles-buliding-blocks, and the molecular formula is C6H4N2O, Reference of 89324-17-4.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Kotani, Shunsuke; Sakamoto, Midori; Osakama, Kazuki; Nakajima, Makoto published the artcile< A Sterically Congested α-Cyanoamine as a Cyanating Reagent: Cyanation of Acetals and Orthoesters>, Formula: C6H11NO2, the main research area is alkoxy alkanenitrile nitrile cyanation.

The cyanation of acetals and ortho-esters by using a sterically congested α-cyanoamine as a cyanation reagent was investigated. The α-cyanoamine effectively facilitated cyanation in the presence of trichlorosilyl triflate to produce a variety of cyanated adducts in excellent yields. Anal. of the reaction mixture by 1H NMR spectroscopy revealed that trichlorosilyl triflate produced an oxocarbenium cation species as an intermediate. Under optimized conditions the synthesis of the target compounds was achieved using 1,1,1-trifluoromethanesulfonic acid trichlorosilyl ester as a reagent and 2-(dicyclohexylamino)acetonitrile (cyanation agent amine-cyanide) and (dimethoxymethyl)benzene (benzaldehyde acetal), (3,3-dimethoxy-1-propen-1-yl)benzene, (dimethoxymethyl)cyclohexane, 1,1′-[(phenylmethylene)bis(oxymethylene)]bis[benzene], 2-phenyl-1,3-dioxolane (cyclic acetal) as starting materials. The title compounds thus formed included α-(methoxy)benzeneacetonitrile derivatives, α-(methoxy)-1-naphthaleneacetonitrile, 2-methoxy-4-phenyl-2-butenenitrile, α-(2-hydroxyethoxy)benzeneacetonitrile. Ortho-ester reactants included (trimethoxymethyl)benzene, 1,1′,1”-[methylidynetris(oxy)]tris[ethane] and 1,1,1-triethoxypentane. Products therefrom included α,α-dimethoxybenzeneacetonitrile.

European Journal of Organic Chemistry published new progress about Acetals Role: RCT (Reactant), RACT (Reactant or Reagent). 6136-93-2 belongs to class nitriles-buliding-blocks, and the molecular formula is C6H11NO2, Formula: C6H11NO2.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Chen, Peng; Zhuang, Yu-Xin; Diao, Peng-Cheng; Yang, Fang; Wu, Shao-Yu; Lv, Lin; You, Wen-Wei; Zhao, Pei-Liang published the artcile< Synthesis, biological evaluation, and molecular docking investigation of 3-amidoindoles as potent tubulin polymerization inhibitors>, Synthetic Route of 38487-85-3, the main research area is amidoindole preparation antiproliferative mol docking tubulin inhibitor human; 3-Amidoindoles; Antiproliferative activity; Microtubules; Tubulin polymerization.

A series of novel 3-amidoindole derivatives possessing 3,4,5-trimethoxylphenyl groups I [R1 = H, Me, Cl, OMe; R2 = 2-thienyl, Ph, 4-FC6H4, etc.] was synthesized and evaluated for their antiproliferative and tubulin polymerization inhibitory activities. Some of them demonstrated moderate to potent activities in vitro against six cancer cell lines including MCF-7, MDA-MB-231, BT549, T47D, MDA-MB-468, and HS578T. The most active compound I [R1 = Cl; R2 = 4-ClC6H4] inhibited the growth of T47D, BT549, and MDA-MB-231 cell lines with IC50 values at 0.04, 3.17, and 6.43 μM, resp. Moreover, the flow cytometric anal. clearly revealed that compound I [R1 = Cl; R2 = 4-ClC6H4] significantly inhibited growth of breast cancer cells through arresting cell cycle in G2/M phase via a concentration-dependent manner. In addition, the compound I [R1 = Cl; R2 = 4-ClC6H4] also exhibited the most potent anti-tubulin activity with IC50 values of 9.5 μM, which was remarkable, compared to CA-4. Furthermore, mol. docking anal. demonstrated the interaction of the compound I [R1 = Cl; R2 = 4-ClC6H4] at the colchicine-binding site of tubulin.

European Journal of Medicinal Chemistry published new progress about Antiproliferative agents. 38487-85-3 belongs to class nitriles-buliding-blocks, and the molecular formula is C8H8N2O, Synthetic Route of 38487-85-3.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Sanchez-Viesca, F.; Gomez, M. R. published the artcile< Anomalous Hoesch reaction>, Category: nitriles-buliding-blocks, the main research area is Hoesch reaction ethoxyacetonitrile; methane methoxyphenyl; acetonitrile ethoxy Hoesch reaction; methoxybenzene Hoesch reaction ethoxyacetonitrile; acetophenone dichlorotrimethoxy reaction.

Treating 1,2,4-trimethoxybenzene (I) with (EtO)2CHCN gave II instead of the Hoesch product III (R = R1 = EtO)(IV). Similar treatment of I with EtOCH2CN gave III (R = H, R1 = Cl). IV could not be prepared from III (R = R1 = Cl).

Revista Latinoamericana de Quimica published new progress about 6136-93-2. 6136-93-2 belongs to class nitriles-buliding-blocks, and the molecular formula is C6H11NO2, Category: nitriles-buliding-blocks.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Moderhack, Dietrich published the artcile< N-unsubstituted tetrazolocarboxaldehyde>, Application In Synthesis of 6136-93-2, the main research area is tetrazolecarboxaldehyde; aldehyde tetrazolyl.

The title compound was prepared by the cyclization of (EtO)2CHCN with N3H in the presence of pyridine to give I [R = CH(OEt)2], which was treated with HCl to give the aldehyde, which exists in the solid form as the dimer II. Upon dissolving in dry Me2SO at 80°, II gave 90% I (R = CHO), which undergoes most of the normal aldehyde reactions, e.g., aldol condensation. Reaction of I (R = CHO) with piperidine gave the unstable salt III, which upon exposure to air gave IV.

Chemiker-Zeitung published new progress about 6136-93-2. 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

Sun, Huan; Jiang, Yue; Lu, Ming-Kun; Li, Yun-Yun; Li, Li; Liu, Ji-Kai published the artcile< Iron-Catalyzed Tandem Radical Addition/Cyclization: Highly Efficient Access to Methylated Quinoline-2,4-diones>, Application In Synthesis of 38487-85-3, the main research area is methyl quinoline dione preparation; cyanoaryl acrylamide dimethyl sulfoxide photochem methylation iron catalyst.

A visible-light-induced and iron-catalyzed oxidative radical addition/cyclization cascade reaction of N-(o-cyanoaryl)acrylamides I [R1 = 4-Cl, 5-CF3, 3-Br, etc.; R2 = Me, Bn; R3 = Me, [(2,2-dimethylpropanoyl)oxy]methyl, Bn, Ph, (acetyloxy)methyl, (1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)methyl] with DMSO has been developed. The method exhibits a wide substrate scope and an excellent functional-group tolerance, thus providing an efficient and convenient access to a variety of methylated quinoline-2,4-diones II (R4 = 6-Cl, 6-CF3, 5-Br, etc.).

Synlett published new progress about Acrylamides 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, Application In Synthesis of 38487-85-3.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Patterson, Andrew W.; Peltier, Hillary M.; Ellman, Jonathan A. published the artcile< Expedient Synthesis of N-Methyl Tubulysin Analogues with High Cytotoxicity>, Related Products of 6136-93-2, the main research area is asym synthesis methyl tubulysin analog alkylation acylation heterocyclization esterification.

An optimized and highly efficient synthesis of potent, bioactive N-Me tubulysin analogs I and II has been achieved with > 40% overall yields. This synthesis represents a significant improvement over previously reported syntheses of these and related tubulysin analogs. The stereoselective synthesis of the unnatural amino acid tubuvaline is accomplished using tert-butanesulfinamide chem. N-Alkylation to form N-Me tubuvaline is performed without protection of the tubuvaline alc. by implementing a unique N-methylation strategy via formation and reduction of a 1,3-tetrahydrooxazine heterocycle. Acylation of the hindered N-Me tubuvaline amine utilizes a novel sequence of O-acylation followed by an O- to N-acyl transfer to form the hindered amide bond between N-Me tubuvaline and isoleucine. This high-yielding synthesis should enable the production of large quantities of material for biol. studies.

Journal of Organic Chemistry published new progress about Alkylation. 6136-93-2 belongs to class nitriles-buliding-blocks, and the molecular formula is C6H11NO2, Related Products of 6136-93-2.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts