Author: Jessica.F

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

Leowanawat, Pawaret published the artcileZero-Valent Metals Accelerate the Neopentylglycolborylation of Aryl Halides Catalyzed by NiCl₂-Based Mixed-Ligand Systems, Application In Synthesis of 214360-44-8, the publication is Journal of Organic Chemistry (2010), 75(22), 7822-7828, database is CAplus and MEDLINE.

The highly active mixed-ligand catalytic system NiCl₂(dppp)/dppf combined with the reducing effect of zerovalent Zn and of other metals was used to demonstrate a method for the dramatic acceleration of the rate and for the enhancement of the yield of Ni-catalyzed neopentylglycolborylation of aryl halides. A diversity of electron-rich and electron-deficient aryl iodides, bromides, and chlorides were efficiently neopentylglycolborylated, typically in 1 h or less. This acceleration is particularly remarkable for the generally less reactive aryl bromides and chlorides and for all ortho-substituted aryl halides. By accelerating the rate of borylation and reducing its reaction time to complete conversion, pathways leading to protodeborylated or hydrodehalogenated side products have a reduced impact on the outcome of the overall reaction. Although Zn powder was the reducing agent of choice, compatibility of this technique with more readily recoverable Zn chips, as well as other metals such as Mn, Mg, Fe, Al, and Ca, demonstrated the broad scope of this synthetic method.

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, Application In Synthesis of 214360-44-8.

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

Quan, Xue-Jing published the artcilep-Toluenesulfonic Acid Mediated 1,3-Dipolar Cycloaddition of Nitroolefins with NaN₃ for Synthesis of 4-Aryl-NH-1,2,3-triazoles [Erratum to document cited in CA161:682131], Name: (E)-4-(2-Nitrovinyl)benzonitrile, the publication is Organic Letters (2015), 17(2), 393, database is CAplus and MEDLINE.

On page 5730, structure 4a in Scheme 2 was published incorrectly, and subsequent text corresponding to this Structure is also incorrect; the correct structure, name, and text are given.

Organic Letters published new progress about 5153-73-1. 5153-73-1 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Alkenyl,Nitro Compound,Benzene, name is (E)-4-(2-Nitrovinyl)benzonitrile, and the molecular formula is C9H6N2O2, Name: (E)-4-(2-Nitrovinyl)benzonitrile.

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

Quan, Xue-Jing published the artcilep-Toluenesulfonic Acid Mediated 1,3-Dipolar Cycloaddition of Nitroolefins with NaN₃ for Synthesis of 4-Aryl-NH-1,2,3-triazoles, Safety of (E)-4-(2-Nitrovinyl)benzonitrile, the publication is Organic Letters (2014), 16(21), 5728-5731, database is CAplus and MEDLINE.

A p-TsOH-mediated 1,3-dipolar cycloaddition of nitroolefins and sodium azide for the synthesis of 4-aryl-NH-1,2,3-triazoles has been developed. p-TsOH was discovered as a vital additive in this type of 1,3-dipolar cycloaddition This novel cycloaddition reaction is a good method for the rapid synthesis of valuable 4-aryl-NH-1,2,3-triazoles in high yields.

Organic Letters published new progress about 5153-73-1. 5153-73-1 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Alkenyl,Nitro Compound,Benzene, name is (E)-4-(2-Nitrovinyl)benzonitrile, and the molecular formula is C9H6N2O2, Safety of (E)-4-(2-Nitrovinyl)benzonitrile.

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

Benmohammed, Abdelmadjid published the artcileSynthesis and antimicrobial activities of new thiosemicarbazones and thiazolidinones in indole series, Quality Control of 612-13-5, the publication is Monatshefte fuer Chemie (2021), 152(8), 977-986, database is CAplus.

New thiosemicarbazones I [R¹ = H, 3-Cl, 4-F, etc.; R² = H, OMe] were synthesized via condensation of N-benzylindole-3-carboxaldehydes with N⁴-substituted thiosemicarbazides in excellent yield. These thiosemicarbazones I were reacted with Et bromoacetate to produce original heterocyclic-substituted indole derivatives possessing a 4-oxo-thiazolidine group II. Anal. IR and NMR spectra and elemental anal. were performed to reveal their structures. The antimicrobial activity of all synthesized compounds was evaluated for antibacterial activity in vitro against Gram-pos. and Gram-neg. bacteria. Antibacterial screening data showed that two compounds I and II demonstrated activity against Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa. These preliminary results indicated that newly synthesized compounds such as I [R¹ = 3-Cl, R² = OMe] and II [R¹ = H, R² = H] showed a promising antibacterial potency.

Monatshefte fuer Chemie published new progress about 612-13-5. 612-13-5 belongs to nitriles-buliding-blocks, auxiliary class Organic Pigment, name is 2-(Chloromethyl)benzonitrile, and the molecular formula is C8H6ClN, Quality Control of 612-13-5.

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

Sochacka-Cwikla, Aleksandra published the artcileSynthesis and biological activity of new 7-amino-oxazolo[5,4-d]pyrimidine derivatives, Recommanded Product: 2-Aminomalononitrile 4-methylbenzenesulfonate, the publication is Molecules (2020), 25(15), 3558, database is CAplus and MEDLINE.

The synthesis of a series of novel 7-aminooxazolo[5,4-d]pyrimidines I (R = Me, Et, cyclohexyl, etc.), transformations during their synthesis and their physicochem. characteristics have been described. Complete detailed spectral anal. of the intermediates, the N’-cyanooxazolylacetamidine byproducts and final compounds I was carried out using MS, IR, 1D and 2D NMR spectroscopy. Theor. research was carried out to explain the privileged formation of 7-aminooxazolo[5,4-d]pyrimidines in relation to the possibility of their isomer formation and the related thermodn. aspects. Addnl., the single-crystal X-ray diffraction anal. for compound I [R = 2-(morpholin-4-yl)ethyl] was reported. Ten 7-aminooxazolo[5,4-d]pyrimidines I were biol. tested in vitro to preliminarily evaluate their immunol., antiviral and anticancer activity. Compounds I [R = n-pentyl, 3-(N,N-dimethylamino)propyl] showed the best immunoregulatory profile. These compounds displayed low-toxicity and strongly inhibited phytohemagglutinin A-induced proliferation of human peripheral blood lymphocytes and lipopolysaccharide-induced proliferation of mouse splenocytes. Compound I [R = 3-(N,N-dimethylamino)propyl] caused also a moderate suppression of tumor necrosis factor α (TNF-α) production in a human whole blood culture. Of note, the compounds also inhibited the growth of selected tumor cell lines and inhibited replication of human herpes virus type-1 (HHV-1) virus in A-549 cell line. Mol. investigations showed that the compounds exerted differential changes in expression of signaling proteins in Jurkat and WEHI-231 cell lines. The activity of the compound I (R = n-pentyl) is likely associated with elicitation of cell signaling pathways leading to cell apoptosis.

Molecules 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 C5H8N2O, Recommanded Product: 2-Aminomalononitrile 4-methylbenzenesulfonate.

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

Maripally, Narsimulu published the artcileDMAP catalyzed addition-cyclization reaction of 2-hydroxyphenyl-para-quinone methide with nitroalkenes: facile entry into highly substituted chromane derivatives, SDS of cas: 5153-73-1, the publication is Tetrahedron Letters (2020), 61(9), 151554, database is CAplus.

The base catalyzed reaction of 2-hydroxyphenyl-para-quinone methide (p-QM) with nitroalkenes was reported. The DMAP-catalyzed reaction afforded substituted chromane derivatives I [R = H, 7-Me, 6-MeO, 6-F, 6-Cl, 6-Br; R¹ = i-Bu, Ph, 2-thienyl, etc.; stereo = R or S] in excellent yields with moderate diastereoselectivity. The conversion of the initial products to other useful structures was also achieved.

Tetrahedron Letters published new progress about 5153-73-1. 5153-73-1 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Alkenyl,Nitro Compound,Benzene, name is (E)-4-(2-Nitrovinyl)benzonitrile, and the molecular formula is C9H6N2O2, SDS of cas: 5153-73-1.

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

Gull, Yasmeen published the artcileSynthesis of N-(6-arylbenzo[d]thiazole-2-acetamide) derivatives and their biological activities: an experimental and computational approach, Related Products of nitriles-buliding-blocks, the publication is Molecules (2016), 21(3), 66/1-66/17, database is CAplus and MEDLINE.

Synthesis of N-(6-arylbenzo[d]thiazol-2-yl)acetamides I [Ar = Ph, 4-MeC₆H₄, 3-Cl-4-FC₆H₃, etc.] by C-C coupling methodol. in the presence of Pd(0) using various aryl boronic pinacol ester/acids was reported. The newly synthesized compounds I were evaluated for various biol. activities like antioxidant, hemolytic, antibacterial and urease inhibition. In bioassays these I compounds were found to have moderate to good activities. Among the tested biol. activities screened these I compounds displayed the most significant activity for urease inhibition. In urease inhibition, all compounds were found more active than the standard used. The compound I [Ar = Ph, 4-MeC₆H₄] was found to be the most active. To understand this urease inhibition, mol. docking studies were performed. The in silico studies showed that these acetamide derivatives bind to the non-metallic active site of the urease enzyme. Structure-activity studies revealed that H-bonding of compounds with the enzyme was important for its inhibition.

Molecules published new progress about 479411-95-5. 479411-95-5 belongs to nitriles-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Nitrile,Boronic acid and ester,Benzene,Boronate Esters,Boronic Acids,Boronic acid and ester, name is 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-5-(trifluoromethyl)benzonitrile, and the molecular formula is C14H15BF3NO2, Related Products of nitriles-buliding-blocks.

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