Month: December 2022

Kikushima, Kotaro published the artcileCopper-mediated one-pot synthesis of trifluorostyrene derivatives from tetrafluoroethylene and arylboronate, Quality Control of 214360-44-8, the publication is Chemistry Letters (2015), 44(7), 1019-1021, database is CAplus.

The copper-mediated synthesis of trifluorostyrenes ArCF:CF₂ (Ar = C₆H₅, 4-MeOC₆H₄, 2-naphthyl, etc.) from aryl boronates and tetrafluoroethylene through the transmetalation-carbocupration-β-fluorine elimination process under one-pot procedure was described. β-Fluorine elimination of a 2-aryl-1,1,2,2-tetrafluoroethylcopper complex, generated in situ from arylboronate, copper tert-butoxide, and 1,10-phenanthroline/bathophenanthroline with tetrafluoroethylene via carbocupration, was promoted by the addition of a Lewis acid.

Chemistry Letters published new progress about 214360-44-8. 214360-44-8 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Boronic acid and ester,Benzene,Boronic Acids,Boronic acid and ester, name is 4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile, and the molecular formula is C12H14BNO2, Quality Control of 214360-44-8.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Somawardhana, C. W. published the artcileRadiopharmaceutical for differential diagnosis of tuberculoma: synthesis of carbon-11 labeled 2-[¹¹C]cyanoisonicotinic acid hydrazide, Application In Synthesis of 135048-32-7, the publication is Applied Radiation and Isotopes (1991), 42(6), 559-62, database is CAplus.

The radiochem. synthesis of 2-[¹¹C]cyanoisonicotinic acid hydrazide (I) was accomplished. Carbon-11 cyano group was introduced at the 2-position of the pyridine ring of 1-methoxy-4-methoxycarbonyl pyridinium Me sulfate via a Reissert-Kaufmann type reaction. The reaction was performed on a solid support (silica gel) to yield no-carrier-added Me 2-[¹¹C]cyano-isonicotinate in (32.4%) yield. This method is unique for the incorporation of [¹¹C]HCN to base sensitive substrates. The carbon-11-labeled Me ester was treated with hydrazine to give I. The final radiochem. yield was 10% and the synthesis time was approx. 35 min.

Applied Radiation and Isotopes published new progress about 135048-32-7. 135048-32-7 belongs to nitriles-buliding-blocks, auxiliary class Pyridine,Nitrile,Hydrazine,Amine,Hydrazide,Amide, name is 2-Cyanoisonicotinohydrazide, and the molecular formula is C9H10O4, Application In Synthesis of 135048-32-7.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Sato, Nobuhiro published the artcileStudies on pyrazines. 17. An efficient synthesis of pteridine-6-carboxylic acids, Application of 2-Aminomalononitrile 4-methylbenzenesulfonate, the publication is Journal of Heterocyclic Chemistry (1988), 25(6), 1737-40, database is CAplus.

2,4-Diaminopteridine-6-carboxylic acid (I) and pterin-6-carboxylic acid (II) were prepared by permanganate oxidation of the corresponding 6-(2-furyl)-substituted pteridines under mild conditions. Several attempts to cleave the furan ring with other oxidizing agents are also described.

Journal of Heterocyclic Chemistry published new progress about 5098-14-6. 5098-14-6 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Salt,Sulfonic acid,Amine,Benzene, name is 2-Aminomalononitrile 4-methylbenzenesulfonate, and the molecular formula is C10H11N3O3S, Application of 2-Aminomalononitrile 4-methylbenzenesulfonate.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Ohashi, Masato published the artcilePalladium-catalyzed base-free Suzuki-Miyaura coupling reactions of fluorinated alkenes and arenes via a palladium fluoride key intermediate, Product Details of C12H14BNO2, the publication is European Journal of Organic Chemistry (2013), 2013(3), 443-447, database is CAplus.

A new strategy for C-C bond formation with organoboronates through C-F activation of fluorinated alkenes and arenes was developed. In this Pd-catalyzed Suzuki-Miyaura-type cross-coupling reaction, neither a base for enhancing the reactivity of the organoboron reagents nor a Lewis acid for promoting C-F bond activation was required. A fluoro-palladium intermediate played an essential role in this reaction. In addition, a Ni(NHC) catalyst was efficient for C-C coupling through C-F bond activation of fluoroarenes.

European Journal of Organic Chemistry published new progress about 214360-44-8. 214360-44-8 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Boronic acid and ester,Benzene,Boronic Acids,Boronic acid and ester, name is 4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile, and the molecular formula is C12H14BNO2, Product Details of C12H14BNO2.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Yu, Euy Kyung published the artcileStudies on the synthesis of the 2-desamino and 2-desamino-2-methyl analogs of aminopterin intermediate at pteridine-C₇ side chain, SDS of cas: 5098-14-6, the publication is Journal of the Korean Chemical Society (1993), 37(1), 131-5, database is CAplus.

Title aminopterin intermediates I (R = H, Me, NH₂) were prepared from pyrazine II. Thus, dithiobisbenzoate III was reduced by NaBH₄ and then treated with II to give pyrazine IV. The cyclization of IV with RC(:NH)NH₂.HCl (R = H, Me, NH₂) in the presence of NaOEt followed by basic hydrolysis gave I (R = H, Me, NH₂).

Journal of the Korean Chemical Society published new progress about 5098-14-6. 5098-14-6 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Salt,Sulfonic acid,Amine,Benzene, name is 2-Aminomalononitrile 4-methylbenzenesulfonate, and the molecular formula is C9H9NO, SDS of cas: 5098-14-6.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Franzen, H. published the artcileAction of cyanides on aldehydes and ketones, HPLC of Formula: 13312-84-0, the publication is Journal fuer Praktische Chemie (Leipzig) (1914), 293-306, database is CAplus.

cf. C. A., 7, 775. The crystalline metallic derivatives previously obtained by shaking cyanides of the alk. earths in H₂O with AcCH₂CO₂Et, BzCH₂CO₂Et, and Ac₂CH₂ are not metallic derivatives of cyanohydrins as then supposed, but metallic salts of the diketones and ketonic esters. The Ca, Sr, Ba and Mg salts of AcCH₂CO₂Et were prepared and the constitution of the Ca salt of mandelonitrile, Ca[OCH(CN)Ph]₂, was proven by its conversion into the Bz derivative, by shaking the Ca salt in Et₂O with BzCl. o-Calcium chloromandelonitrile was obtained in 62% yield from CaO, HCN and o-ClC₆H₄CHO, light yellow powder. The calcium, strontium and magnesium salts of Ac₂CH₂ were obtained in the form of needles from alc. From P-MeC₆H₄CHO was obtained, in 63% yield, calcium p-methylmandelonsirile in the form of orange-yellow crystals, which gave an intense blue coloration with concentrate H₂SO₄. p-Calcium methoxymandelonitrile was prepared from anisaldehyde. The labile, crystalline compound obtained by Kohn (Monalsh., 20, 903) by the action of HCHO on Ca(CN)₂, is shown to have the constitution Ca[OCH(CaOH)CN]₂.AcH forms a similar compound, crystallization powder. KCN and AcH yielded alanine and α-iminodipropionic acid.

Journal fuer Praktische Chemie (Leipzig) published new progress about 13312-84-0. 13312-84-0 belongs to nitriles-buliding-blocks, auxiliary class Chloride,Nitrile,Benzene,Alcohol,Benzene Compounds, name is 2-(2-Chlorophenyl)-2-hydroxyacetonitrile, and the molecular formula is C8H6ClNO, HPLC of Formula: 13312-84-0.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Mailig, Melrose published the artcilePractical catalytic method for synthesis of sterically hindered anilines, Quality Control of 214360-44-8, the publication is Chemical Communications (Cambridge, United Kingdom) (2015), 51(55), 11048-11051, database is CAplus and MEDLINE.

A practical catalytic method for the synthesis of sterically hindered anilines is described. The amination of aryl and heteroaryl boronic esters is accomplished using a catalyst prepared in situ from com. available and air-stable copper(I) triflate and a diphosphine ligand. For the first time, the method can be applied to the synthesis of both secondary and tertiary anilines in the presence of a wide range of functional groups. Esters, aldehydes, alcs., aryl halides, ketones, nitriles and nitro arenes are all compatible with the reaction conditions. Finally, even the most sterically hindered anilines can be successfully prepared under mild reaction conditions. Overall, the new method addresses significant practical limitations of a transformation previously developed and provides a valuable complement to the existing methods for the synthesis of anilines. Under optimized conditions the synthesis of the target compounds was achieved using 1,1′-(oxydi-2,1-phenylene)bis[1,1-dicyclohexylphosphine] (i.e. phosphine-ether) and copper(I) triflate compound with benzene (2:1) as ligand-catalyst combination. Starting materials included N-(benzoyloxy)-N-(1-methylethyl)-2-propanamine (hydroxylamine derivative), benzoic acid 1-pyrrolidinyl ester, 4-(benzoyloxy)-1-piperazinecarboxylic acid 1,1-dimethylethyl ester, benzoic acid 4-morpholinyl ester, benzoic acid 4-hydroxy-1-piperidinyl ester, benzoic acid 2,2,6,6-tetramethyl-1-piperidinyl ester. Boronic acid cyclic esters included 5,5-dimethyl-2-(2-methylphenyl)-1,3,2-dioxaborinane, 4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile, 4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzoic acid ester, 4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzaldehyde, 2-chloro-3-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)pyridine, 5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)pyrimidine, 5,5-dimethyl-2-(3-thienyl)-1,3,2-dioxaborinane (thiophene derivative). The title compounds thus formed included 4-bromo-N,N-bis(1-methylethyl)benzenamine (tertiary amine, tertiary aniline), 2,6-dimethyl-N-(1-methylethyl)benzenamine (secondary amine, secondary aniline). The reaction of a [1,1′-(oxydi-2,1-phenylene)bis[1,1-dicyclohexylphosphine-.kappa .P]]copper complex intermediate with N-(benzoyloxy)-2-methyl-2-propanamine was reported.

Chemical Communications (Cambridge, United Kingdom) published new progress about 214360-44-8. 214360-44-8 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Boronic acid and ester,Benzene,Boronic Acids,Boronic acid and ester, name is 4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile, and the molecular formula is C12H14BNO2, Quality Control of 214360-44-8.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Fischer, H. published the artcilePyrrolenitriles and some of their transformations, Related Products of nitriles-buliding-blocks, the publication is Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen (1930), 2249-57, database is CAplus.

2,4-Dimethyl-3-cyano-5-carbethoxypyrrole, MeC:C(CN).CMe:CR.NH (I, R = CO₂Et) is saponified to the 5-CO₂H acid (II) (I, R =CO₂H) without the CN group being hydrolyzed, and distillation in vacuo gives 2,4-dimethyl-3-cyanopyrrole (III). The CN group is materially stabilized by its position on the nucleus, whereas when it is on a side chain, as in 2,4-dimethyl-3-Ω-cyano-Ω-carbetboxy-vinyl-5-carbethoxypyrrole, it can be hydrolyzed with extraordinary ease, the β-position being attacked first and then the α-position. III can be obtained still more easily by the Knorr pyrrole synthesis from AcCH₂CO₂Et and AcCH₂CONH₂, and AcCH₂NH₂.HCl instead of AcCH₂CO₂Et-NaNO₂ gives an even better yield. With HCHO and a little HCl III readily yields 3,3′,5,5′-tetramethyl-4,4′-dicyanopyrrometliane (IV) which, surprisingly enough, cannot be converted with either FeCl₃ or Br into the corresponding methene (V) although the V.HBr is obtained in good yield, with elimination of CO₂, from II with HCO₂H and 48% HBr on the H₂O bath. NH₄OH readily gives the free V in red needles which form metal complexes. III and HCN readily give an aldehyde (VI) (1, R = CHO), whose oxime yields with AC₂O 2,4-dimethyl-3,5-dicyanopyrrole (VII). With boiling HCl VI yields V.HCl. The CHO group in VI is reduced to Me by the Wolff-Kishner method, giving 2,4,5-trimethyl-3-eyanopyrrole, together with some 2,4,5-trimethylpyrrole. From VI and 2,3,4-trimethylpyrrole, cryptopyrrole and crypto-pyrrolecarboxylic acid were obtained 3,3′,4,5,5′-pentamethyl- (VII), 3,3′,5,5′-tetramethyl-4-ethyl- (VIII) and 3,3′,5,5′-ietramethyl-4-propionic acid-4′-cyanopyrromethene-HBr (IX), resp.; VIII was also obtained from cryptopyrrolealdehyde with III. These cyanomethenes were synthesized with the object of preparing porphyrins with CN groups on the nucleus but numerous attempts to do this failed. Porphyrin formation took place but only etioporphyrin II could be isolated. This negative result is perhaps due to the unreactiveness of the α-Me groups. Bromination of the 3 methenes could not be effected either and I (R = CO₂Et) is likewise unreactive toward Br, although with Br and NaBrO₃ 3 Br atoms can be introduced into the α-Me group, with simultaneous oxidation of the α-Me group, the product being 2-tribromomethyl-3-cyano-4-hydroxymethyl-5-carbethoxypyrrole (X). III can also be brominated on the nucleus in the α-position. With SO₂Cl₂ I gave a yellow oil yielding with H₂O 2-hydroxymethyl-3-cyano-4-methyl-5-carbethoxypyrrole (XI). With higher concentrations, 6 atoms Cl are introduced: the product is probably 2,4-bistrichloromethyl-3-cyano-5-carbethoxypyrrole (XII). II (about 40 g. from 60 g. I with boiling aqueous NaOH), m. 250°; 8 g. in vacuo at 150° gives 4 g. III, m. 107°. 2,4-Dimethyl-3-carboxamide-5-carbethoxypyrrole (1.8 g. from 12 g. AcCH₂-CO₂Et, NaNO₂, AcCH₂CONH₂ and Zn dust), m. 173°; 0.5 g. gives with boiling NaOAc-Ac₂O 0.3 g. I, which is obtained in 1 g. yield from 1.5 g. ACCH₂NH₂.HCl and AcCH-CONH₂ in NaOH. V.HBr (13-5 g. from 20 g. II), golden yellow, in. 242° (decomposition). V.HCl (1 g. from 2 g. II), m. 225° (decomposition). Free V, ruby-red, m. 280°(decomposition); Cu complex, C₃0H₂6N₈C₁1 crystals with metallic green surface luster, soluble in most solvents with red color; Co complex, green; On complex, 2C₃0H₂6N₈Zn.Zn(OAc)₂, pink, contains 2 active H atoms (Chugaev-Zerevitinov). XI, reddens and sinters 145-°, m. around 195-6°. XII (2.8 g. from 5 g. I, 20 g. SO₂Cl₂ and 20 cc. Et₂O), m. around 98°. X (about 20%), m. 183°, easily soluble in dilute alkalies, the yellow solution becoming dark brown and finally black (in 20% NaOH it at once darkens and decomposes), regenerates I on long boiling with Zn dust in AcOH. 2,4-Dimethyl-3-cyano-5-formylpyrrole (VI) (9-10 g. from 15 g. III in CHCl₃-Et₂O with anhydrous HCN), m. 223° oxime, m. 206°; semicarbazone, turns yellow 250° and gradually darkens and sinters; phenylhydrazone, m. 175°. VII, m. 209°. 2,4-Dimethyl-3-cya-no-5-bromopyrrole (0-5 g. from 0.4 g. III with Br-AcOH), darkens 130° and sinters without melting. VII (1.3g. from 0.75g. VI), yellow, decomposes 230°. VIII (80%), orange-red, darkens 190°, m. 241° IX, golden yellow, m. 240° (decomposition).

Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen published new progress about 26187-28-0. 26187-28-0 belongs to nitriles-buliding-blocks, auxiliary class Pyrrole,Nitrile, name is 2,4-Dimethyl-1H-pyrrole-3-carbonitrile, and the molecular formula is C7H8N2, Related Products of nitriles-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Perez-Garcia, Raul M. published the artcileMild, organo-catalysed borono-deamination as a key to late-stage pharmaceutical precursors and ¹⁸F-labelled radiotracers, Synthetic Route of 214360-44-8, the publication is Frontiers in Chemistry (Lausanne, Switzerland) (2022), 884478, database is CAplus and MEDLINE.

A tris(pentafluorophenyl)borane catalyzed method for the synthesis of boronic acid esters from aromatic amines in yields of up to 93% was devised. Mild conditions, benign reagents, short reaction times, low temperatures and a wide substrate scope characterize the method. The reaction was found applicable to the synthesis of boronic acid ester derivatives of complex drug mols. in up to 86% isolated yield and high purity suitable for labeling. These boronates were subsequently labeled with [18F] fluoride ion in radiochem. yields of up to 55% with and even without isolation of the boronate-intermediate.

Frontiers in Chemistry (Lausanne, Switzerland) published new progress about 214360-44-8. 214360-44-8 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Boronic acid and ester,Benzene,Boronic Acids,Boronic acid and ester, name is 4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile, and the molecular formula is C12H14BNO2, Synthetic Route of 214360-44-8.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts