Month: January 2023

One-Pot Synthesis of Spirocyclopenta[a]indene Derivatives via a Cascade Ring Expansion and Intramolecular Friedel-Crafts-Type Cyclization was written by Li, Quanzhe;Liu, Jiaxin;Wei, Yin;Shi, Min. And the article was included in Journal of Organic Chemistry in 2020.Safety of 2-Amino-4-(trifluoromethyl)benzonitrile This article mentions the following:

A one-pot efficient synthetic approach for the rapid construction of spirocyclopenta[a]indene derivatives has been developed via an iodine-initiated cascade ring expansion and intramol. Friedel-Crafts-type cyclization from propargyl alc.-tethered alkylidenecyclobutanes under mild conditions with broad substrate scope. This cascade process can be elegantly conducted on a gram scale. A plausible reaction mechanism has been proposed on the basis of a series of deuterium labeling and control experiments In the experiment, the researchers used many compounds, for example, 2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1Safety of 2-Amino-4-(trifluoromethyl)benzonitrile).

2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1) belongs to nitriles. Nitrile compounds can be prepared by the incorporation of a cyanide source through C–C bond formation or by dehydration of primary carboxamides. Nitriles are susceptible to hydrogenation over diverse metal catalysts. The reaction can afford either the primary amine (RCH2NH2) or the tertiary amine ((RCH2)3N), depending on conditions.Safety of 2-Amino-4-(trifluoromethyl)benzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Organorhodium-Functionalized Periodic Mesoporous Organosilica: High Hydrophobicity Promotes Asymmetric Transfer Hydrogenation in Aqueous Medium was written by Liu, Rui;Jin, Ronghua;Kong, Lingyu;Wang, Jinyu;Chen, Chen;Cheng, Tanyu;Liu, Guohua. And the article was included in Chemistry – An Asian Journal in 2013.Name: (R)-4-(1-Hydroxyethyl)benzonitrile This article mentions the following:

Three organosilica-bridged periodic mesoporous organosilicas were prepared by the immobilization of a chiral N-sulfonylated diamine-based organorhodium complex within their silicate network. Structural anal. and characterization confirmed their well-defined single-site active rhodium centers, while electron microscopy revealed their highly ordered hexagonal mesostructures. Among these three different organosilica-bridged periodic mesoporous organosilicas, the ethylene-bridged periodic mesoporous organosilica catalyst exhibited excellent heterogeneous catalytic activity and high enantioselectivity in the aqueous asym. transfer hydrogenation of aromatic ketones. This superior catalytic performance was attributed to its salient hydrophobicity, while its comparable enantioselectivity relative to the homogeneous catalyst was derived from the confined nature of the chiral organorhodium catalytic sites. Furthermore, this ethylene-bridged periodic mesoporous organosilica could be conveniently recovered and reused at least 12 times without the loss of its catalytic activity. This feature makes this catalyst attractive for practical organic synthesis in an environmentally friendly manner. This study offers a general way of optimizing the bridged organosilica moiety in periodic mesoporous organosilicas, thereby enhancing its catalytic activity in heterogeneous catalysis. In the experiment, the researchers used many compounds, for example, (R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6Name: (R)-4-(1-Hydroxyethyl)benzonitrile).

(R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6) belongs to nitriles. The electronic structure of nitriles is very similar to that of an alkyne with the main difference being the presence of a set of lone pair electrons on the nitrogen. In conventional organic reductions, nitrile is reduced by treatment with lithium aluminium hydride to the amine. Reduction to the imine followed by hydrolysis to the aldehyde takes place in the Stephen aldehyde synthesis, which uses stannous chloride in acid.Name: (R)-4-(1-Hydroxyethyl)benzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Density function theory study on anthracene substituted by dicyanovinyl in different positions was written by Zhang, Jinglai;Miao, Tifang;Wang, Hua;Tian, Anmin. And the article was included in Huaxue Tongbao in 2003.Application of 55490-87-4 This article mentions the following:

Results of RHF(RHF) and d. function theory(DFT) calculations are reported for 2-dicyanovinyl anthracene(2-DCVA) and 9-dicyanovinyl anthracene(9-DCVA) at B3LYP/6-311+G(d,p)//RHF/6-31G(d,p) level. The equilibrium geometries of 2-DCVA and 9-DCVA have been optimized and the harmonic vibrational frequencies have been calculated The calculating results show that the ground state of 9-DCVA is higher than that of 2-DCVA in total energy. Having revolved angles between anthracene and dicyanovinyl from -180.0° to 180.0°, their potential energy curves are obtained to find their equilibrium geometries, The results show that there are two different stable geometries in energy and a transition geometry for 2-DCVA while there are a stable geometry and two transition geometries for 9-DCVA, the structure of 2-DCVA is more planar than 9-DCVA. At PM3/CIS level, their electronic spectrum were calculated and the vertical excitation energies and corresponding oscillator strengths from the ground states to the excited states are obtained. These results are in good agreement with the results obtained from experiment In the experiment, the researchers used many compounds, for example, 2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4Application of 55490-87-4).

2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4) belongs to nitriles. The R-C-N bond angle in and nitrile is 180° which give a nitrile functional group a linear shape. Both the carbon and the nitrogen are sp hydridized which leaves them both with two p orbitals which overlap to form the two π bond in the triple bond. Nitriles are susceptible to hydrogenation over diverse metal catalysts. The reaction can afford either the primary amine (RCH2NH2) or the tertiary amine ((RCH2)3N), depending on conditions.Application of 55490-87-4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthesis, characterization, and antibacterial and anti-inflammatory activities of new pyrimidine and thiophene derivatives was written by Lahsasni, Siham;Al-Hemyari, Dunya A. M.;Ghabbour, Hazem A.;Mabkhoot, Yahia Nasser;Aleanizy, Fadilah S.;Alothman, Asma A.;Almarhoon, Zainab M.. And the article was included in Journal of Chemistry in 2018.Electric Literature of C8H8N2S This article mentions the following:

Substituted[4,5]thieno[2,3-d]thiazolo[3,2-a]pyrimidin-5-ones and pyrimidin-5(6H)-imines, compounds I [X = O, NH; Y = (CH₂)_n; n = 1-3] were synthesized via reaction of the starting compounds, Et 2-amino-substituted[b]thiophene-3-carboxylates and 2-amino-substituted [b]thiophene-3-carbonitriles, resp., with 2-bromothiazole. Synthesis of (bromo-substituted[b]thiophen-2-yl) alkanamides, compds II [R = CN, COOEt; Z = (CH₂)_m; n = 1-3; m = 3, 4] and thieno[2,3-d][1,3]oxazin-4-imine was accomplished via reaction of the starting compounds with bromoalkyl chloride through nucleophilic substitution; however, for the synthesis of this compound, nucleophilic substitution was followed by nucleophilic addition to a nitrile group to form the oxazinimine ring. 1-(3-Cyano-substituted[b]thiophen-2-yl)-3-(4-(trifluoromethyl)phenyl)thioureas, compound III [n = 1-3] were obtained via reaction of the starting compounds and 4-(trifluoromethyl phenyl)isothiocyanate. The lead compounds rapidly reacted with 4-(trifluoromethyl)benzaldehyde or 4-(2-pyridyl)benzaldehyde in acidic medium to yield compounds IV [R¹ = CF₃, 2-pyridyl, n = 1-3] in large quantities. X-ray crystallog. of compounds II [R = CN, n = 3] and IV [R¹ = CF₃, n = 3] confirmed their structures. Antimicrobial studies revealed that compound III [n = 1] was equally potent to ampicillin against Bacillus strains. Moreover, compounds I [X = NH, n = 3], II [R = COOEt, n = 3], and III [n = 1] possessed greater anti-inflammatory potency than that of the standard drug. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2Electric Literature of C8H8N2S).

2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2) belongs to nitriles. There has been no report on the microbial biosynthesis of nitriles and the physiological function of such enzymes, nor was it not even known whether aliphatic and aromatic nitriles are biological compounds or just petrochemicals. Nitriles are susceptible to hydrogenation over diverse metal catalysts. The reaction can afford either the primary amine (RCH2NH2) or the tertiary amine ((RCH2)3N), depending on conditions.Electric Literature of C8H8N2S

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

The [CoN₄(OH)(OH₂)]²⁺ (N₄ = trpn, cyclen and tren) promoted hydrolysis of the phosphotriester 2,4-dinitrophenyl diethyl phosphate was written by Hay, Robert W.;Govan, Norman. And the article was included in Transition Metal Chemistry (Dordrecht, Netherlands) in 1998.Reference of 7528-78-1 This article mentions the following:

The [CoL(OH₂)₂]³⁺ (L = trpn, cyclen and tren) promoted hydrolysis of the phosphotriester 2,4-dinitrophenyl di-Et phosphate to give di-Et phosphate and 2,4-dinitrophenolate was studied in detail over the pH range 3-7.5. The pK values of the various complexes were determined at 25° and I = 0.1 mol dm^-3 by potentiometric titration The pH-rate profiles for the reactions are consistent with the hydroxoaqua complex [CoL(OH)(OH₂)]²⁺ being the active species in the hydrolysis. No evidence for saturation kinetics was obtained and values of k_cat determined at pH 7 and 25° (I = 0.1 mol dm^-3) are 4.24 × 10^-3 dm³ mol^-1 s^-1 (tren) < 3.05 × 10^-2 dm³ mol^-1 s^-1 (cyclen) < 7.5 × 10^-1 dm³ mol^-1 s^-1 (trpn). Studies involving the more reactive phosphonate ester 2,4-dinitrophenyl Et methylphosphonate suggest that the rate-determining step in the reaction is the decomposition of the ternary complex between the Co(III) complex and the phosphotriester. The rate enhancement using 0.01 mol dm^-3 Co(trpn)³⁺ is some 4.6 × 10⁴ fold at pH 7 and 25°. In the experiment, the researchers used many compounds, for example, 3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1Reference of 7528-78-1).

3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1) belongs to nitriles. The electronic structure of nitriles is very similar to that of an alkyne with the main difference being the presence of a set of lone pair electrons on the nitrogen. Nitrile groups in organic compounds can undergo a variety of reactions depending on the reactants or conditions. A nitrile group can be hydrolyzed, reduced, or ejected from a molecule as a cyanide ion.Reference of 7528-78-1

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Condensation of 3-methyl-6-nitrobenzonitrile and 3-methyl-6-nitrobenzamide with benzaldehyde was written by Macovski, Eugen;Georgescu, Julia. And the article was included in Trav. lab. chim. biol., Faculté sci., Univ. Bucarest in 1946.Recommanded Product: 64113-86-6 This article mentions the following:

Nitration of m-MeC₆H₄CN gives a mixture of 3-methyl-6-nitrobenzonitrile (I), m. 92°, and isomeric nitro compounds removable by steam distillation The distillate with KOH-H₂O₂ gives 3-methyl-2-nitrobenzamide (II), m. 192°, and 3-methyl-5-nitrobenzamide (III), m. 166°. Heating II with BzH 2 hrs. at 160° gives N,N’-benzylidenebis(3-methyl-2-nitrobenzamide), m. 243°; III gives N,N’-benzylidenebis(3-methyl-5-nitrobenzamide), m. 235-7°. I with KOH-H₂O₂ gives 3-methyl-6-nitrobenzamide (IV), m. 176-7°, not hydrolyzed by alc. NaOMe at 37°. BzH converts IV into N,N’-benzylidenebis(3-methyl-6-nitrobenzamide), m. 263°. IV with BzH in the presence of piperidine at 160° gives 3-carbamyl-4-nitrostilbene (V), m. 241°; hydrolysis of 3-cyano-4-nitrostilbene by KOH-H₂O₂ and condensation of IV with BzH in the presence of NaOEt at 37° also give V. In the experiment, the researchers used many compounds, for example, 5-Methyl-2-nitrobenzonitrile (cas: 64113-86-6Recommanded Product: 64113-86-6).

5-Methyl-2-nitrobenzonitrile (cas: 64113-86-6) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. Nitrile groups in organic compounds can undergo a variety of reactions depending on the reactants or conditions. A nitrile group can be hydrolyzed, reduced, or ejected from a molecule as a cyanide ion.Recommanded Product: 64113-86-6

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Expedient one-pot synthesis of indolo[3,2-c]isoquinolines via a base-promoted N-alkylation/tandem cyclization was written by Nguyen, Huy H.;Fettinger, James C.;Haddadin, Makhluf J.;Kurth, Mark J.. And the article was included in Tetrahedron Letters in 2015.Computed Properties of C8H5F3N2 This article mentions the following:

A transition metal-free one-pot protocol for the synthesis of 11H-indolo[3,2-c]isoquinolin-5-amines I [R¹ = 9-Me, 9-Cl, 8,9-(MeO)₂, etc.; R² = H, 2-F, 2-MeO] via the atom economical annulation of Et (2-cyano-phenyl)carbamates and 2-cyanobenzyl bromides was developed. This mild and efficient method proceeds via sequential N-alkylation and base-promoted cyclization. Furthermore, optimization data, substrate scope, mechanistic insights and photoluminescence properties were also discussed. In the experiment, the researchers used many compounds, for example, 2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1Computed Properties of C8H5F3N2).

2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1) belongs to nitriles. Nitrile function is a very important functional group because it can be manipulated to other functional groups such as carboxylic acid by hydrolysis or amine by reduction, respectively. Nitrile groups in organic compounds can undergo a variety of reactions depending on the reactants or conditions. A nitrile group can be hydrolyzed, reduced, or ejected from a molecule as a cyanide ion.Computed Properties of C8H5F3N2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Platinum Assisted Tandem P-C Bond Cleavage and P-N Bond Formation in Amide Functionalized Bisphosphine o-Ph₂PC₆H₄C(O)N(H)C₆H₄PPh₂-o: Synthesis, Mechanistic, and Catalytic Studies was written by Kunchur, Harish S.;Balakrishna, Maravanji S.. And the article was included in Inorganic Chemistry in 2022.Computed Properties of C14H12N2 This article mentions the following:

The reactions of amide functionalized bisphosphine o-Ph₂PC₆H₄C(O)N(H)C₆H₄PPh₂-o (1) with Pt salts is described. Treatment of 1 with [Pt(COD)Cl₂] yielded a chelate complex, [PtCl₂{o-Ph₂PC₆H₄C(O)N(H)C₆H₄PPh₂-o}κ²-P,P] (2), which on subsequent treatment with LiHMDS formed a novel 1,2-azaphospholene-phosphine complex [PtPhCl{o-C₆H₄{C(O)N(o-PPh₂(C₆H₄))P(Ph)}}κ²-P,P] (3) involving a tandem P–C bond cleavage and P-N bond formation. The same complex 3 on passing dry HCl gas afforded dichloro-complex [PtCl₂{o-C₆H₄{C(O)N(o-PPh₂(C₆H₄))P(Ph)}}κ²-P,P] (5). Complex 2 upon refluxing in toluene or treatment of 1 with [Pt(COD)Cl₂] in the presence of a base at room temperature resulted in pincer complex [PtCl{o-Ph₂PC₆H₄C(O)N(C₆H₄PPh₂-o)}κ³-P,N,P] (4). Reaction of 1 with [Pt(COD)ClMe] at room temperature also afforded the pincer complex [PtMe{o-Ph₂PC₆H₄C(O)N(C₆H₄PPh₂-o)}κ³-P,N,P] (6). Mechanistic studies on 1,2-azaphospholene formation showed the reductive elimination of LiCl to form a phosphonium salt that readily adds one of the P-C bonds oxidatively to the in situ generated Pt⁰ species to form a chelate complex 3. Analogous Pd complex [PdCl₂{o-C₆H₄{C(O)N(o-PPh₂(C₆H₄))P(Ph)}}κ²-P,P] (7) showed excellent catalytic activity toward N-alkylation of amines with alcs. with a very low catalyst loading (0.05 mol %), and the methodol. is very efficient toward the gram scale synthesis of many N-alkylated amines. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Computed Properties of C14H12N2).

4-(Benzylamino)benzonitrile (cas: 10282-32-3) belongs to nitriles. Nitrile compounds can be prepared by the incorporation of a cyanide source through C–C bond formation or by dehydration of primary carboxamides. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).Computed Properties of C14H12N2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthesis of substituted thieno[2,3-b]pyrroles was written by Wei, Hongtao;Cai, Jin;Sun, Min;Ji, Min. And the article was included in Heteroatom Chemistry in 2007.Application In Synthesis of Ethyl 5-amino-4-cyano-3-(2-ethoxy-2-oxoethyl)thiophene-2-carboxylate This article mentions the following:

Thieno[2,3-b]pyrroles were synthesized through three steps: Gewald synthesis, alkylation, and Thorpe-Ziegler cyclization. Di-Et 3,6-bis((ethoxycarbonyl)methyl)-4-amino-6H-thieno-[2,3-b]pyrrole-2,5- dicarboxylate was obtained by one-pot method in DMF in good yield and high quality. In the experiment, the researchers used many compounds, for example, Ethyl 5-amino-4-cyano-3-(2-ethoxy-2-oxoethyl)thiophene-2-carboxylate (cas: 58168-20-0Application In Synthesis of Ethyl 5-amino-4-cyano-3-(2-ethoxy-2-oxoethyl)thiophene-2-carboxylate).

Ethyl 5-amino-4-cyano-3-(2-ethoxy-2-oxoethyl)thiophene-2-carboxylate (cas: 58168-20-0) belongs to nitriles. Nitrile compounds can be prepared by the incorporation of a cyanide source through C–C bond formation or by dehydration of primary carboxamides. Alkyl nitriles are sufficiently acidic to undergo deprotonation of the C-H bond adjacent to the CN group.Strong bases are required, such as lithium diisopropylamide and butyl lithium. The product is referred to as a nitrile anion. Application In Synthesis of Ethyl 5-amino-4-cyano-3-(2-ethoxy-2-oxoethyl)thiophene-2-carboxylate

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

N-Alkylation of aniline derivatives by use of potassium cation-exchanged Y-type zeolite was written by Onaka, Makoto;Umezono, Akihiro;Kawai, Motomitsu;Izumi, Yusuke. And the article was included in Journal of the Chemical Society, Chemical Communications in 1985.Formula: C14H12N2 This article mentions the following:

Zeolite K-Y effectively promoted the N-alkylation of p-RC₆H₄NH₂ (R = NO₂, CN, CO₂Et, H, Cl, Me) with R¹Br (R¹ = CH₂CH:CH₂, CH₂Ph) or Me₂SO₄ in PhMe or C₆H₆ at 50°-reflux for 5-15 h to give 55-90% yield of 3.9-50:1 mixtures of p-RC₆H₄NHR¹ and p-RC₆H₄NR¹₂ (R as before, R¹ = CH₂CH:CH₂, CH₂Ph, Me). Results were compared with those for the analogous γ-alumina-promoted alkylation. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Formula: C14H12N2).

4-(Benzylamino)benzonitrile (cas: 10282-32-3) belongs to nitriles. Nitrile function is a very important functional group because it can be manipulated to other functional groups such as carboxylic acid by hydrolysis or amine by reduction, respectively. In conventional organic reductions, nitrile is reduced by treatment with lithium aluminium hydride to the amine. Reduction to the imine followed by hydrolysis to the aldehyde takes place in the Stephen aldehyde synthesis, which uses stannous chloride in acid.Formula: C14H12N2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts