Category: nitriles-buliding-blocks

On November 26, 1986, Koeckritz, Peter; Liebscher, Juergen; Schmidt, Ludmilla published a patent.Computed Properties of 2510-01-2 The title of the patent was Preparation of 2,3,N,N-tetrasubstituted-1,1-dicyano-4-amino-1,3-butadienes useful as intermediates for analgesics, etc.. And the patent contained the following:

The title compounds (R2)2NCH:CR1CR:C(CN)2 [I; R, R1 = H, (un)substituted alkyl or alkenyl, aryl, heteroaryl; RR1 = (CH2)3-5, CH2NH(CH2)2, benzo-condensed alkenylene, e.g., o-C6H4CH2CH2; R2 = alkyl; R2R2 = (CH2)4-5, (CH2)2O(CH2)2, (CH2)2NH(CH2)2], useful as intermediates for heterocyclic compounds with antiphlogistic, analgesic, or antirheumatic activity, are prepared by reacting R1CH2CR:C(CN)2 with (R2)2NCH(OR3)2 (R3 = alkyl) in the presence of a protonic acid. A solution of Me2C:C(CN)2 in AcOH was treated with (R2)2NCH(OMe)2 [R2R2 = (CH2)2O(CH2)2] and the mixture was warmed to boiling to give 81% I [R = Me, R1 = H, R2R2 = (CH2)2O(CH2)2]. The experimental process involved the reaction of 2-(2,3-Dihydro-1H-inden-1-ylidene)malononitrile(cas: 2510-01-2).Computed Properties of 2510-01-2

The Article related to analgesic intermediate aminocyanobutadiene preparation, antiphlogistic intermediate aminocyanobutadiene preparation, antirheumatic intermediate aminocyanobutadiene preparation, heterocycle intermediate aminocyanobutadiene preparation, aminocyanobutadiene preparation heterocycle intermediate, cyanobutadiene amino preparation heterocycle intermediate and other aspects.Computed Properties of 2510-01-2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

On October 10, 2002, Mattson, Ronald; Denhart, Derek; Deskus, Jeffrey; Ditta, Jonathan; Marcin, Lawrence; Epperson, James; Catt, John; King, Dalton; Higgins, Mendi published a patent.Reference of 2-(2-Nitro-4-(trifluoromethyl)phenyl)acetonitrile The title of the patent was Preparation of cyclopropylindoles as selective serotonin reuptake inhibitors. And the patent contained the following:

Treatment of depression, anxiety disorders, premature ejaculation, chronic pain, obsessive-compulsive disorder, feeding disorders, premenstrual dysphoric disorder, panic disorders and psychotic disorders including bipolar disorder and schizophrenia. Title compounds [I; A1, A2 = alkylene, bond; A3 = alkylene, alkylidene; A4 = alkylene, bond; X, X1, X2 X3 = C, CH; J = alkyl; p = 0, 1; R1, R2 = H, alkyl, (substituted) cycloalkyl, Ph, PhO , NHCO2alkyl, alkylNHCO2, thienyl, furanyl, pyrrolyl, pyrrolinyl, pyrrolidinyl, imidazolyl, imidazolinyl, imidazolidinyl, pyrazolyl, pyrazolinyl, pyrazolidinyl, pyridyl, pyrimidinyl, piperidinyl, piperazinyl, morpholino, adamantyl, indolyl, isoindolyl, indolinyl, quinolinyl, dihydroquinolinyl, tetrahydroquinolinyl, isoquinolinyl, dihydroisoquinolinyl, tetrahydroisoquinolinyl; or A1R1 and A2R2 together with the N to which they are attached = pyrrolyl, pyrrolinyl, pyrrolidinyl, imidazolyl, imidazolinyl, imidazolidinyl, pyrazolyl, pyrazolinyl, pyrazolidinyl, pyridyl, pyrimidinyl, piperidinyl, piperazinyl, morpholino, adamantyl, indolyl, isoindolyl, indolinyl, quinolinyl, dihydroquinolinyl, tetrahydroquinolinyl, isoquinolinyl, dihydroisoquinolinyl, tetrahydroisoquinolinyl and are optionally substituted with halo, alkyl, alkoxy, cyano, benzyl; R3 = H, alkyl; m = 0, 1; R4, R5 = H, cyano, halo, NO2, perfluoroalkyl; n = 0, 1; G = N, O, S; G1 = N, CH; Y = DH; D = C; Z = EH; E = C; with provisos], were prepared for treatment of depression, anxiety, premature ejaculation, chronic pain, obsessive-compulsive disorder, feeding disorders, premenstrual dysphoric disorder, panic disorder, and psychotic disorders including bipolar disorder and schizophrenia. Thus, a solution of di-Et (N-methoxy-N-methylcarbamoylmethyl)phosphonate in THF was added to a stirred suspension of sodium hydride in THF at 0°; the reaction was warmed to room temperature and was stirred for 2 h; After cooling to 0°, [5-cyano-1-(p-toluenesulfonyl)indol-3-yl]carboxaldehyde (preparation given) was added. The resulting mixture was stirred at 0° for 1 h to give 91% (E)-[5-cyano-1-(p-toluenesulfonyl)indol-3-yl]-N-methoxy-N-methylacrylamide. This was converted to trans-2-(5-cyanoindol-3-yl)-1-(N,N-dimethylaminomethyl)cyclopropane in several steps. The latter showed serotonin transporter binding with Ki<1 nM. The experimental process involved the reaction of 2-(2-Nitro-4-(trifluoromethyl)phenyl)acetonitrile(cas: 13544-06-4).Reference of 2-(2-Nitro-4-(trifluoromethyl)phenyl)acetonitrile

The Article related to cyclopropylindole preparation selective serotonin reuptake inhibitor, indole cyclopropyl preparation selective serotonin reuptake inhibitor, depression anxiety premature ejaculation obsessive compulsive disorder treatment cyclopropylindole, feeding disorder premenstrual dysphoric disorder panic disorder treatment cyclopropylindole and other aspects.Reference of 2-(2-Nitro-4-(trifluoromethyl)phenyl)acetonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

On April 14, 2011, Nakao, Akira; Suzuki, Hiroko; Tatsumi, Ryo; Setsuta, Tomofumi; Seki, Maki; Iwasaki, Hiroshi; Zheng, Zhongli; Makara, Gergely; Dai, Chaoyang; Siddiqui, Arshad; Kawahata, Noriyuki; Nan, Yang published a patent.Computed Properties of 34662-29-8 The title of the patent was Preparation of bis(glycinamide) derivatives as homocysteine synthase inhibitors. And the patent contained the following:

There are disclosed homocysteine synthase inhibitors which are useful for the prevention or treatment of diseases associated with a homocysteine synthase, e.g. arteriosclerosis, cerebral infarction, or myocardial infarction. There are specifically disclosed N-(carbamoylmethyl)glycinamide compounds represented by general formula [I; R1 = H, C1-3 alkyl; R2 = (un)substituted heterocyclyl containing at least one N atom in the ring, NR2aR2b; R2a, R2b = H, C1-6 alkyl, haloalkyl, (un)substituted aryl; R3 = H; R4, R5, R6, R7 = H, C1-4 alkyl; L = [C(R8a)(R8b)]s[C(R8c)(R8d)]t; s, t = an integer of 0-2; R8a, R8b, R8c, R8d = H, C1-3 alkyl; Ar = l = an integer of 0-4; X = O, S; R9 = each (un)substituted C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-8 cycloalkyl, heterocyclyl, aryl, heteroaryl, or arylalkyl; R10 = halo, cyano, C1-6 alkyl, CF3, HO, C1-4 alkoxy, CF3O, COR12, each (un)substituted NH2, aryl, heteroaryl, heterocyclyl, C1-6 alkyl-S(O)m; R12 = HO, C1-6 alkyl, C1-6 alkoxy, (un)substituted NH2; m = an integer of 0-2; A = each (un)substituted aryl, aryl-C1-4 alkyl, heteroaryl-C1-4 alkyl, C3-6 alkynyl, or C3-8 cycloalkyl, Q1, Q2, etc.; n = an integer of 0-2; h = 0, 1; i = 1, 2; R14 = C1-4 alkyl, W = :CH, :N], pharmacol. acceptable salts of the compounds, or solvates of the compounds or the pharmacol. acceptable salts. Thus, N-[5-chloro-2-(4-chlorophenoxy)phenyl]-N-[2-[(1,3-dihydro-2H-isoindol-2-yl)(methyl)amino]-2-oxoethyl]glycine 412, tert-Bu (2-aminoethyl)methylcarbamate hydrochloride 270, and 1-hydroxybenzotriazole 181 mg were dissolved in 1 mL DMF and 10 mL CH2Cl2, treated with 265 mg 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, and stirred at room temperature for 3 h to give, after workup and silica gel chromatog., 75% N’-[5-chloro-2-(4-chlorophenoxy)phenyl]-N’-[2-[(1,3-dihydro-2H-isoindol-2-yl)(methyl)amino]-2-oxoethyl]-N-[2-[(tert-butoxycarbonyl)(methyl)amino]ethyl]glycinamide (II) (407 mg). II (387 mg) was dissolved in 2 mL CH2Cl2, treated with 2.0 mL 4 N HCl/dioxane solution at room temperature, and stirred at room temperature for 90 min, and treated with Et2O for precipitation of a solid which was filtered off and dried under reduced pressure to give 64% N’-[5-chloro-2-(4-chlorophenoxy)phenyl]-N’-[2-[(1,3-dihydro-2H-isoindol-2-yl)(methyl)amino]-2-oxoethyl]-N-[2-(methylamino)ethyl]glycinamide (III) dihydrochloride. III.2HCl in vitro showed IC50 of 2.6 nM for inhibiting the hydrolysis of S-adenosyl-L-homocysteine by human recombinant S-adenosyl-L-homocysteine hydrolase. The experimental process involved the reaction of 3-Chloro-4-nitrobenzonitrile(cas: 34662-29-8).Computed Properties of 34662-29-8

The Article related to bisglycinamide derivative preparation homocysteine synthase inhibitor, carbamoylmethylglycinamide preparation homocysteine synthase inhibitor, adenosyl homocysteine hydrolase inhibitor bisglycinamide derivative preparation, arteriosclerosis cerebral infarction myocardial infarction prevention treatment bisglycinamide preparation and other aspects.Computed Properties of 34662-29-8

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

On September 11, 1991, Evans, Richard A.; Lorencak, Primoz; Ha, Tae Kyu; Wentrup, Curt published an article.SDS of cas: 5098-14-6 The title of the article was HCN dimers: iminoacetonitrile and N-cyanomethanimine. And the article contained the following:

Iminoacetonitrile H(NC)C:NH (I) has been prepared by two methods: (i) thermal decomposition of the tosylhydrazone salts H2N(NC)C:NN-TosM+ (Tos = tosyl, M = Na, Li) at 200° and (ii) Ar matrix photolysis of azidoacetonitrile. Ab initio calculations indicate that Z-I is of slightly lower energy than E-I, and this is confirmed by the IR spectra with use of the thermal methods. E-I/Z-I undergo photochem. interconversion, giving a ca. 3:1 photostationary E:Z ratio. E-I and Z-I are fully characterized by their gas-phase, matrix, and thin-film IR spectra, which are in excellent agreement with ab initio calculations, by 1H and 13C NMR spectroscopy in solution, and by mass spectrometry. I polymerizes in solution above -40°; pyrolysis produces HCN, and matrix photolysis produces HNC and van der Waals complexes containing HNC. N-tert-Butyliminoacetonitrile thermally fragments to tert-Bu isocyanide and HCN. N-Cyanomethanimine H2C:NCN (II) has also been prepared by two methods: (i) pyrolysis of trimethylenetetrazole (III) at 500-800° and (ii) pyrolysis of ditetrazolopyrazine (IV) at 600-850°. Both methods are extremely clean. II is fully characterized by its IR spectrum in agreement with ab initio calculations and, in conjunction with other work, by its mass and millimeter-wave spectra. II is thermodynamically stable in the gas phase up to ca. 800° at low pressure and short contact times but polymerizes in the solid state above -100°. The experimental process involved the reaction of 2-Aminomalononitrile 4-methylbenzenesulfonate(cas: 5098-14-6).SDS of cas: 5098-14-6

The Article related to hydrogen cyanide dimer iminoacetonitrile cyanomethanimine, spectra iminoacetonitrile cyanomethanimine, ab initio iminoacetonitrile cyanomethanimine, polymerization iminoacetonitrile cyanomethanimine, photochem isomerization iminoacetonitrile, pyrolysis iminoacetonitrile cyanomethanimine precursor, photolysis iminoacetonitrile and other aspects.SDS of cas: 5098-14-6

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Martin, Nazario; Quinteiro, Margarita; Seoane, Carlos; Soto, Jose L. published an article in 1987, the title of the article was Synthesis of some polyheterocyclic systems with isolated nuclei.SDS of cas: 75629-62-8 And the article contains the following content:

Knoevenagel-type condensation reactions of heterocyclic aldehydes were carried out. Thus, treatment of RCHO (R = pyridyl, pyrrolyl, furyl, etc.) with active methylene compounds PhCOCH2R1 (R1 = CN, CO2Et) in EtOH containing piperidine afforded benzoylheteroarylacrylonitrile and -acrylates RCH:CR1COPh (I). The I underwent cyclization with malononitrile to give 4H-pyrans II. The experimental process involved the reaction of 2-((1H-Indol-3-yl)methylene)malononitrile(cas: 75629-62-8).SDS of cas: 75629-62-8

The Article related to pyrancarbonitrile heteroaryl, pyridineacrylonitrile benzoyl, furanacrylonitrile benzoyl, pyrroleacrylonitrile benzoyl, thiopheneacrylonitrile benzoyl, indoleacrylonitrile benzoyl, aldehyde knoevenagel condensation benzoylacetonitrile, acetonitrile benzoyl condensation aldehyde, acetate benzoyl condensation aldehyde and other aspects.SDS of cas: 75629-62-8

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

On July 25, 2022, Zhu, Lixiang; Peng, Heling; Guo, Yan; Che, Jixing; Wu, Jia-Hong; Su, Zhishan; Wang, Tianli published an article.Reference of 2-(2,3-Dihydro-1H-inden-1-ylidene)malononitrile The title of the article was Enantioselective Synthesis of Atropisomeric Biaryl Phosphorus Compounds by Chiral-Phosphonium-Salt-Enabled Cascade Arene Formation. And the article contained the following:

Axially chiral biaryl monophosphorus mols., exemplified by atropisomeric 1,1′-biaryl aminophosphines, are significant motifs in numerous chiral ligands/catalysts. Developing efficient methods for preparing P compounds with these privileged motifs is an important endeavor in synthetic chem. Herein, the authors develop an effective, modular method by a chiral-phosphonium-salt-catalyzed novel cascade between P-containing nitroolefins and α,α-dicyanoolefins, leading to a great diversity of atropisomeric biaryls bearing P groups in high yields with excellent stereoselectivities. The reaction features include a Thorpe-type cycloaddition/oxidative hydroxylation/aromatization cascade pathway with a central-to-axial chirality transfer process. Insight gained from the authors’ studies is expected to advance general efforts towards the catalytic synthesis of atropisomeric biaryl P compounds, offering a platform for developing new efficient chiral ligands and catalysts. The experimental process involved the reaction of 2-(2,3-Dihydro-1H-inden-1-ylidene)malononitrile(cas: 2510-01-2).Reference of 2-(2,3-Dihydro-1H-inden-1-ylidene)malononitrile

The Article related to naphthyl nitroolefin cycloaddition cyanoolefin chiral phosphonium salt catalyst, aminophosphorylnaphthalenylnitro dihydrophenanthrene carbonitrile derivative preparation crystal structure, mol structure aminophosphorylnaphthalenylnitro dihydrophenanthrene carbonitrile derivative, atropisomerism, biaryl phosphines and other aspects.Reference of 2-(2,3-Dihydro-1H-inden-1-ylidene)malononitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Seck, Pierre; Thomae, David; Perspicace, Enrico; Hesse, Stephanie; Kirsch, Gilbert published an article in 2012, the title of the article was Synthesis of new selenophene and thiazole analogues of the tacrine series.Application of 5098-14-6 And the article contains the following content:

New 2-aminoselenophene-3-carbonitriles and 5-amino-1,3-thiazole-4-carbonitriles were prepared and reacted with cycloalkanones to give tetrahydroselenolo[2,3-b]quinolines, cycloalkene-fused selenolo[3,2-e]pyridines, [1,3]thiazolo[5,4-b]quinolines, thiazolo[4,5-e]pyridines, and tetrahydro-[1,3]thiazolo[5,4-b]quinolines. The experimental process involved the reaction of 2-Aminomalononitrile 4-methylbenzenesulfonate(cas: 5098-14-6).Application of 5098-14-6

The Article related to selenophene tacrine analog preparation, thiazole tacrine analog preparation, hydroselenoloquinoline preparation, cycloalkene fused selenolopyridine preparation, thiazoloquinoline cycloalkene fused preparation, thiazolopyridine cycloalkene fused preparation, hydrothiazoloquinoline cycloalkene fused preparation and other aspects.Application of 5098-14-6

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

On April 29, 2005, Xue, Dong; Chen, Ying-Chun; Cui, Xin; Wang, Qi-Wei; Zhu, Jin; Deng, Jin-Gen published an article.Electric Literature of 2510-01-2 The title of the article was Transfer Hydrogenation of Activated C:C Bonds Catalyzed by Ruthenium Amido Complexes: Reaction Scope, Limitation, and Enantioselectivity. And the article contained the following:

It was found that the chemoselectivity could be completely switched from C:O to C:C bonds in the transfer hydrogenation of activated α,β-unsaturated ketones R1CH:CR2COR3 (R1 = Ph, 4-MeOC6H4, 4-O2NC6H4; R2 = H, Me, MeCO, EtO2C; R3 = Me, Ph) catalyzed by diamine-ruthenium complex. Moreover, this addition via metal hydride had been applied to the reduction of various activated olefins R4R5C:CR6R7 (R4 = H, Me; R5 = H, n-C5H11, Ph, 4-MeOC6H4, 4-O2NC6H4; R6 = CN, EtO2C, Ph, O2N, etc.; R7 = H, CN, O2N, HO2C, etc.). The electron-withdrawing ability of functional groups substituted on C:C bonds at the α- or β-position had strong influence on the reactivity. In addition, a wide variety of chiral diamine-Ru(II)(arene) systems was investigated to explore the asym. transfer hydrogenation of prochiral α,α-dicyanoolefins. Two parameters had been systematically studied: (i) the structure of the N-sulfonylated chiral diamine ligands and (ii) the structure of the metal precursors. The experimental process involved the reaction of 2-(2,3-Dihydro-1H-inden-1-ylidene)malononitrile(cas: 2510-01-2).Electric Literature of 2510-01-2

The Article related to ketone unsaturated stereoselective chemoselective transfer hydrogenation ruthenium amido complex, dinitrile enantioselective transfer hydrogenation ruthenium amido complex, alkene activated transfer hydrogenation ruthenium amido complex, sulfonamide amino preparation chiral ligand asym transfer hydrogenation and other aspects.Electric Literature of 2510-01-2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

On September 18, 2015, Spallarossa, Andrea; Caneva, Chiara; Caviglia, Matteo; Alfei, Silvana; Butini, Stefania; Campiani, Giuseppe; Gemma, Sandra; Brindisi, Margherita; Zisterer, Daniela M.; Bright, Sandra A.; Williams, Clive D.; Crespan, Emmanuele; Maga, Giovanni; Sanna, Giuseppina; Delogu, Ilenia; Collu, Gabriella; Loddo, Roberta published an article.Quality Control of 2-((1H-Indol-3-yl)methylene)malononitrile The title of the article was Unconventional Knoevenagel-type indoles: Synthesis and cell-based studies for the identification of pro-apoptotic agents. And the article contained the following:

A new series of indole-based analogs were recently identified as potential anticancer agents. The Knoevenagel-type indoles herein presented were prepared via a one-pot condensation of iminium salts with active methylene reagents and were isolated as single geometric isomers. Biol. evaluation in different cell-based assays revealed an antiproliferative activity for some analogs already in the nanomolar range against leukemia, breast and renal cancer cell lines. To explain these effects, the most promising analogs of the series were engaged in further cell-based studies. Compounds I [R1 = R3 = H, R2 = Ph, X = CN, Y = thien-2-yl-(E), SO2Ph-(E); R1 = R3 = H, R2 = Ph, X = C(:O)Me, Y = SO2Ph-(E); R1 = R3 = H, R2 = C6H4OMe-4, X = CN, Y = CN, SO2Ph-(E)] highlighted a pro-apoptotic potential being able to induce apoptosis in HL60, K562 and MCF-7 cell lines in a dose and time-dependent manner. The ability of these compounds to arrest cell cycle at the G2/M phase inspired the immunofluorescence studies which allowed us to identify tubulin as a potential target for compounds (E)-I [R1 = R3 = H, R2 = Ph, X = CN, Y = SO2Ph; R1 = R3 = H, R2 = C6H4OMe-4, X = CN, Y = SO2Ph]. The experimental process involved the reaction of 2-((1H-Indol-3-yl)methylene)malononitrile(cas: 75629-62-8).Quality Control of 2-((1H-Indol-3-yl)methylene)malononitrile

The Article related to unconventional knoevenagel type indole preparation cell based proapoptotic agent, structure activity relationship unconventional knoevenagel type antiproliferative, leukemia proapoptotic agent unconventional knoevenagel type indole, breast cancer proapoptotic agent unconventional knoevenagel type indole and other aspects.Quality Control of 2-((1H-Indol-3-yl)methylene)malononitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

On May 17, 1985, Hennen, William J.; Hinshaw, Barbara C.; Riley, Timothy A.; Wood, Steven G.; Robins, Roland K. published an article.Formula: C10H11N3O3S The title of the article was Synthesis 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. And the article contained the following:

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. The experimental process involved the reaction of 2-Aminomalononitrile 4-methylbenzenesulfonate(cas: 5098-14-6).Formula: C10H11N3O3S

The Article related to aminoribofuranosylthiazole, aminoribofuranosylselanazole, thiazole c nucleoside, selenazole c nucleoside, ribofuranosylthiazolopyrimidine, ribofuranosylselenazolopyrimidine, thiazolopyrimidine ribofuranosyl, selenazolopyrimidine ribofuranosyl, tiazofurin, selenazofurin, nucleoside c thiazole selenazole and other aspects.Formula: C10H11N3O3S

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts