Author: Jessica.F

Chen, Chaohuang published the artcilePalladium(II)-Catalyzed Aminotrifluoromethoxylation of Alkenes: Mechanistic Insight into the Effect of N-Protecting Groups, Category: nitriles-buliding-blocks, the publication is Chinese Journal of Chemistry (2020), 38(4), 346-350, database is CAplus.

An efficient palladium-catalyzed regioselective 5-exo aminotrifluoromethoxylation of alkenes was established herein, which provided a practical route toward the synthesis of OCF₃-containing pyrrolidines such as I [R¹ = H, allyl, 4-ClC₆H₄, etc.; R² = allyl, Bn, 4-FC₆H₄, etc.; R¹R² = (CH₂)₃, (CH₂)₄, (CH₂)₂O(CH₂)₂, etc.] and II. Tert-Butyloxycarbonyl (Boc) as an amino protecting group played a significant role in both chemo- and regioselectivities. In addition, preliminary mechanistic studies revealed that amino protecting group of substrates and counter anion of palladium catalyst play critical roles in reaction efficiency presumably due to an isomerization of alkyl- Pd(II) intermediates. Moreover, the asym. 5-exo aminotrifluoromethoxylation reaction had also been achieved by introducing a sterically bulky pyridinyl-oxazoline ligand.

Chinese Journal of Chemistry published new progress about 68569-14-2. 68569-14-2 belongs to nitriles-buliding-blocks, auxiliary class Palladium, name is Tetrakis(acetonitrile)palladium(II) Ditriflate, and the molecular formula is C10H12F6N4O6PdS2, Category: nitriles-buliding-blocks.

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

Ieda, Naoya published the artcilePhotomanipulation of Vasodilation with a Blue-Light-Controllable Nitric Oxide Releaser, Computed Properties of 26187-28-0, the publication is Journal of the American Chemical Society (2014), 136(19), 7085-7091, database is CAplus and MEDLINE.

Spatiotemporally controllable nitric oxide (NO)-releasers allow us to analyze the physiol. effects of NO, a gaseous mediator that modulates many biol. signaling networks, and are also candidate chemotherapeutic agents. We designed and synthesized a blue-light-controllable NO releaser, named NOBL-1, which bears an N-nitrosoaminophenol moiety for NO release tethered to a BODIPY dye moiety for harvesting blue light. Photoinduced electron transfer from N-nitrosoaniline to the antenna moiety upon irradiation with relatively noncytotoxic blue light (470-500 nm) should result in NO release with formation of a stable quinone moiety. NO release from NOBL-1 was confirmed by ESR spin trapping and fluorescence detection. Spatially controlled NO release in cells was observed with DAR-4M AM, a fluorogenic NO probe. We also demonstrated temporally controlled vasodilation of rat aorta ex vivo by blue-light-induced NO release from NOBL-1. This compound should be useful for precise examination of the functions of NO with excellent spatiotemporal control.

Journal of the American Chemical Society 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, Computed Properties of 26187-28-0.

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

Schoellkopf, Ulrich published the artcileSyntheses with α-metalated isocyanides. XXIX. Higher amino acids by alkylation of α-metalated ethyl α-isocyanopropionate and alkyl isocyanoacetates, Synthetic Route of 30431-99-3, the publication is Chemische Berichte (1975), 108(5), 1580-92, database is CAplus.

Treatment of α-metalated CNCHR1CO2R2 [R1 = Me, R2 = Et (I); R1 = H, R2 = Et (II); R1 = H, R2 = CMe3 (III)] with alkylating agents (R3X, e.g., R3 = Bu, PhCH2, X = Br, Iodo) gave monoalkylation of I and III but dialkylation of II. Hydrolysis of the alkylated products with HCl/EtOH at 25° or KOH/EtOH at 80° gave R1R3C(NH2)CO2R2 or R1R3C(NHCHO)CO2R2, resp. II and III reacted with 1,2-dibromoethane, bis(2-chloroethyl) ether, and 1,4-dibromobutane to give IV, V, and VI, resp.

Chemische Berichte published new progress about 30431-99-3. 30431-99-3 belongs to nitriles-buliding-blocks, auxiliary class Tetrahydropyran,Nitrile,Ester, name is Ethyl 4-cyanotetrahydro-2H-pyran-4-carboxylate, and the molecular formula is C9H13NO3, Synthetic Route of 30431-99-3.

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

Steven, Alan published the artcileUse of a Curtius Rearrangement as Part of the Multikilogram Manufacture of a Pyrazine Building Block, Computed Properties of 5098-14-6, the publication is Organic Process Research & Development (2018), 22(1), 77-81, database is CAplus.

2-Amino-5-methylpyrazine I was prepared on multikilogram scale as an intermediate in the preparation of a glucokinase activator using the Curtius rearrangement of an acyl azide derived from 5-methyl-2-pyrazinecarboxylic acid as the key step. The formation of an acyl azide for the Curtius rearrangement required a process safety control strategy to be put in place. The process developed was used to successfully deliver multikilogram quantities of I in an overall yield of 68% starting from 5-methylpyrazine-2-carboxylic acid.

Organic Process Research & Development 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 C3H12Cl2N2, Computed Properties of 5098-14-6.

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

Huang, Deguang published the artcileReactions of the Terminal Ni^II-OH Group in Substitution and Electrophilic Reactions with Carbon Dioxide and Other Substrates: Structural Definition of Binding Modes in an Intramolecular Ni^II···Fe^II Bridged Site, Application In Synthesis of 68569-14-2, the publication is Journal of the American Chemical Society (2010), 132(13), 4693-4701, database is CAplus and MEDLINE.

A singular feature of the catalytic C-cluster of CO dehydrogenase is a sulfide-bridged Ni···Fe locus where substrate is bound and transformed in the reversible reaction CO + H₂O â‡?CO₂ + 2H⁺ + 2e^–. A similar structure was sought. Mononuclear planar Ni^II complexes [Ni(pyN₂^Me2)L]^1- (pyN₂^Me2 = bis(2,6-dimethylphenyl)-2,6-pyridinedicarboxamidate(2-)) derived from a NNN pincer ligand were prepared including L = OH^– (1) and CN^– (7). Complex 1 reacts with Et formate and CO₂ to form unidentate L = HCO₂^– (5) and HCO₃^– (6) products. A binucleating macrocycle was prepared which specifically binds Ni^II at a NNN pincer site and five-coordinate Fe^II at a triamine site. The Ni^II macrocycle forms [Ni(OH)(pyN₂dien^Me3)L]^1- (14) and [Ni(CN)(pyN₂dien^Me3)L]^1-complexes (15) analogous to 1 and 7. Reaction of 14 with FeCl₂ alone and with Et formate and 15 with FeCl₂ affords mols. with the Ni^II-L-Fe^II bridge unit in [Ni(L)FeCl(⊂pyN₂dien^Me3)]^1- (⊂pyN₂dien^Me3 = I) in which L = μ₂:η¹-OH^– (17) and μ₂:η²-HCO₂^– (18) and -CN^– (19). All bridges are nonlinear (17, 140.0°; 18, M-O-C 135.9° (Ni), 120.2° (Fe); 19, Ni-C-N 170.3°, Fe-N-C 141.8°) with Ni···Fe separations of 3.7-4.8 Å. The Ni^IIFe^II complexes, lacking appropriate Ni-Fe-S cluster structures, are not site analogs, but their synthesis and reactivity provide the 1st demonstration that mol. Ni^II···Fe^II sites and bridges can be attained, a necessity in the biomimetic chem. of C-clusters.

Journal of the American Chemical Society published new progress about 68569-14-2. 68569-14-2 belongs to nitriles-buliding-blocks, auxiliary class Palladium, name is Tetrakis(acetonitrile)palladium(II) Ditriflate, and the molecular formula is C10H12F6N4O6PdS2, Application In Synthesis of 68569-14-2.

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

Sircar, Ila published the artcileNonpeptide angiotensin II receptor antagonists. 2. Design, synthesis, and structure-activity relationships of 2-alkyl-4-(1H-pyrrol-l-yl)-1H-imidazole derivatives: profile of 2-propyl-1-[[2′-(1H-tetrazol-5-yl)-[1,1′-biphenyl]-4-yl]-methyl]-4-[2-(trifluoroacetyl)-1H-pyrrol-1-yl]-1H-imidazole-5-carboxylic acid (CI-996), Synthetic Route of 5098-14-6, the publication is Journal of Medicinal Chemistry (1993), 36(16), 2253-65, database is CAplus and MEDLINE.

A novel series of nonpeptide angiotensin II (AII) receptor antagonists containing a 1H-pyrrol-1-yl moiety at the 4-position of the imidazole have been developed. The pyrrole group occupies the same lipophilic pocket at the receptor as the chloro group in DuP 753 and EXP 3174 (I; R = Bu, R¹ = CH₂OH, CO₂H, R² = Cl, resp.) and the pentafluoro group in DuP 532 (I; R = Pr, R¹ = CO₂H, R² = CF₂CF₃). The impetus for its selection came from bioisosteric considerations based on hydrophobic and electronic substituent constants An extensive study of the structure-activity relationships revealed several highly potent AII receptor antagonists. An acyl substitution at the 2-position of the pyrrole ring improved activity, most notably in the in vivo rat model. In addition, the 2-substituted pyrrole compounds improved chem. stability toward extremely facile decarboxylation reaction associated with unsubstituted pyrrole analogs, thus facilitating development of these agents. The IC₅₀‘s of I [R = Pr, R¹ = CO₂H, R² = 2-(trifluoroacetyl)- (18), 2,5-dimethyl-, or 2,5-dichloro-1H-pyrrol-1-yl] (<1 nM) were better than the reference compounds EXP 3174 and DuP 532. These compounds were selective AII antagonists that compete at the AT₁ receptor and showed no affinity at the AT₂ receptor at concentrations up to 10 M. Upon i.v. administration in a normotensive rat model, compound 18 inhibited the AII-induced responses with ED₅₀ of 6 g/kg per min. In a renal hypertensive rat model, the antihypertensive potency of compound 18, at a dose of 10 mg/kg, was very similar to those of DuP 753 and EXP 3174, resp. Compound 18 demonstrated a dose-related (3-30 mg/kg) decrease in blood pressure that was sustained for greater than 24 h. On the basis of its profile, compound 18, designated as CI-996, has been selected for in-depth studies. The design, synthesis, in vitro, and in vivo structure-activity relationships are described.

Journal of Medicinal 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 C6H16OSi, Synthetic Route of 5098-14-6.

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

Man, Hon-Wah published the artcileA Highly Enantioselective and Diastereoselective Synthesis of Cyclobutanes via Boronic Esters, COA of Formula: C10H18BNO2, the publication is Organic Letters (1999), 1(3), 379-381, database is CAplus and MEDLINE.

Deprotonation of enantiopure (R,R)-1,2-dicyclohexyl-1,2-ethanediol 1-chloro-4-cyanobutylboronates with LDA followed by treatment with anhydrous magnesium bromide yields (R)-(trans-2-cyanocyclobutyl)boronic esters 7 in high diastereomeric and enantiomeric purity. No cyclobutane formation has been observed in the absence of at least a catalytic amount of magnesium halide.

Organic Letters published new progress about 238088-16-9. 238088-16-9 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Boronic acid and ester,Aliphatic cyclic hydrocarbon,Boronic Acids,Boronate Esters, name is 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)butanenitrile, and the molecular formula is C10H18BNO2, COA of Formula: C10H18BNO2.

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

Kitanosono, Taku published the artcileHydrogen-Bonding-Assisted Cationic Aqua Palladium(II) Complex Enables Highly Efficient Asymmetric Reactions in Water, Related Products of nitriles-buliding-blocks, the publication is Angewandte Chemie, International Edition (2021), 60(7), 3407-3411, database is CAplus and MEDLINE.

Metal-bound water mols. have recently been recognized as a new facet of soft Lewis acid catalysis. Herein, a chiral palladium aqua complex was constructed that enables carbon-hydrogen bonds of indoles to be functionalized efficiently. We embraced a chiral 2,2′-bipyridine as both ligand and hydrogen-bond donor to configure a robust, yet highly Lewis acidic, chiral aqua complex in water. Whereas the enantioselectivity could not be controlled in organic solvents or under solvent-free conditions, the use of aqueous environments allowed the σ-indolylpalladium intermediates to react efficiently in a highly enantioselective manner. This work thus describes a potentially powerful new approach to the transformation of organometallic intermediates in a highly enantioselective manner under mild reaction conditions.

Angewandte Chemie, International Edition published new progress about 68569-14-2. 68569-14-2 belongs to nitriles-buliding-blocks, auxiliary class Palladium, name is Tetrakis(acetonitrile)palladium(II) Ditriflate, and the molecular formula is C10H12F6N4O6PdS2, Related Products of nitriles-buliding-blocks.

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

Trost, Barry M. published the artcileHighly Stereoselective Synthesis of α-Alkyl-α-Hydroxycarboxylic Acid Derivatives Catalyzed by a Dinuclear Zinc Complex, Formula: C9H6N2O2, the publication is Angewandte Chemie, International Edition (2012), 51(26), 6480-6483, S6480/1-S6480/101, database is CAplus and MEDLINE.

The authors describe a highly diastereo- and enantioselective nitro-Michael reaction of 5H-oxazol-4-ones. The process provides a range of highly functionalized α-alkyl-α-hydroxycarboxylic acid derivatives in high yields. For example, reacting β-nitrostyrene with methyloxazolone I gave the desired product II in 95% yield (d.r. = 15.6:1, 88% ee) in the presence of ZnEt₂ and phenol ligand III.

Angewandte Chemie, International Edition 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 C30H24BrCuN2P, Formula: C9H6N2O2.

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

Hennen, William J. published the artcileSynthesis of 4-substituted 5-amino-2-(β-D-ribofuranosyl)thiazoles and 4-substituted 5-amino-2-(β-D-ribofuranosyl)selenazoles, and their respective conversion into 2-(β-D-ribofuranosyl)thiazolo[5,4-d]pyrimidines and 2-(β-D-ribofuranosyl)selenazolo[5,4-d]pyrimidines. A new synthesis of tiazofurin and selenazofurin, Application In Synthesis of 5098-14-6, the publication is Journal of Organic Chemistry (1985), 50(10), 1741-6, database is CAplus.

Anhydroallonothioate (I; Z = S) and -selenoate (I; Z = Se), prepared by treatment of anhydroallonimidate (I; Z = NH) with H₂S and H₂Se, underwent cyclocondensation with H₂NCH(CN)₂, NCCN(NH₂)CONH₂, or NCCH(NH₂)CO₂Et to give C-nucleosides II (X = S, R = NH₂, R¹ = cyano; X = S, Se, R = NH₂, R¹ = CONH₂; X = S, Se, R = NH₂, R¹ = CO₂Et). II (X = S, R = NH₂, R¹ = cyano; X = S, Se, R = NH₂, R¹ = CONH₂) were further cyclized with H₂NCH:NH or HC(OEt)₃ to give thiazolo- and selenazolopyrimidine C-nucleosides, e.g., III (X = S, Se). II (X = S, Se, R = NH₂, R¹ = CO₂Et) were converted in 2 steps into tiazofurin and selenazofurin (II; X = S, Se, R = H, R¹ = CONH₂), resp.

Journal of Organic 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 In Synthesis of 5098-14-6.

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