Month: October 2022

Shi, Yongjia; Gao, Qian; Xu, Senmiao published the artcile< Chiral Bidentate Boryl Ligand Enabled Iridium-Catalyzed Enantioselective C(sp3)-H Borylation of Cyclopropanes>, Category: nitriles-buliding-blocks, the main research area is chiral bidentate boryl ligand preparation catalyst iridium borylation cyclopropane; cyclopropanecarboxamide preparation iridium catalyzed enantioselective borylation; crystal structure chiral boryl cyclopropanecarboxamide; mol structure chiral boryl cyclopropanecarboxamide; bioactive Levomilnacipran enantioselective preparation.

The authors herein report an Ir-catalyzed enantioselective C(sp3)-H borylation of cyclopropanecarboxamides using a chiral bidentate boryl ligand for the 1st time. A variety of substrates with α-quaternary C centers could be compatible in this reaction to provide β-borylated products with good to excellent enantioselectivities. Also the borylated products can be used as versatile precursors engaging in stereospecific transformations of C-B bonds, including the synthesis of a bioactive compound Levomilnacipran.

Journal of the American Chemical Society published new progress about Amides Role: PRP (Properties), RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation) (boryl cyclopropanecarboxamides). 658-99-1 belongs to class nitriles-buliding-blocks, and the molecular formula is C8H5F2N, Category: nitriles-buliding-blocks.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Murakami, Teiichi; Otsuka, Masami; Ohno, Masaji published the artcile< An efficient synthesis of 5-diethoxymethylimidazole-4-carboxylate: a potential precursor for various imidazole derivatives>, Name: 2,2-Diethoxyacetonitrile, the main research area is ethoxymethylimidazolecarboxylate; imidazolecarboxylate diethoxymethyl; cycloaddition ethoxyacetonitrile methyl isocyanoacetate; nitrile cycloaddition methyl isocyanoacetate.

The title imidazolecarboxylate I [R = CH(OEt)2] was prepared in 82% yield by cycloaddition reaction of (EtO)2CHCN with CNCH2CO2Me in diglyme containing KH at 0-70° for 5 h. I [R = (MeO)3C, Ph, pyridyl, furyl] were similarly prepared in 13-85% yield.

Tetrahedron Letters published new progress about Cycloaddition reaction. 6136-93-2 belongs to class nitriles-buliding-blocks, and the molecular formula is C6H11NO2, Name: 2,2-Diethoxyacetonitrile.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Flores-Gaspar, Areli; Martin, Ruben published the artcile< Mechanistic Switch via Subtle Ligand Modulation: Palladium-Catalyzed Synthesis of α,β-Substituted Styrenes via C-H Bond Functionalization>, Recommanded Product: 2-(2-Bromo-5-fluorophenyl)acetonitrile, the main research area is palladium catalyst aldehyde bromophenylmethyl olefination; alkene aryl preparation.

A new catalyst system for the efficient use of aldehydes I [R1 = H, F, MeO, etc.; R2 = H, Cl, etc.; R3 = H, 3-HO, 3,5-Me2, etc.] for the synthesis of styrenes II via C-H bond functionalization and a subtle ligand modification is described. The high level of activity achieved allows to synthesize highly functionalized α,β-substituted styrenes, even the elusive E-configured trisubstituted olefins, in a regio- and stereoselective manner. Mechanistic experiments allowed to identify the corresponding synthetic intermediates.

Advanced Synthesis & Catalysis published new progress about Aldehydes Role: RCT (Reactant), RACT (Reactant or Reagent). 886761-96-2 belongs to class nitriles-buliding-blocks, and the molecular formula is C8H5BrFN, Recommanded Product: 2-(2-Bromo-5-fluorophenyl)acetonitrile.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Osipyan, Angelina; Sapegin, Alexander; Novikov, Alexander S.; Krasavin, Mikhail published the artcile< Rare Medium-Sized Rings Prepared via Hydrolytic Imidazoline Ring Expansion (HIRE)>, Synthetic Route of 94087-40-8, the main research area is thiazepine dihydroimidazo alkyl halide hydrolytic imidazoline ring expansion; thiazecine preparation.

The hydrolytic imidazoline ring expansion (HIRE) methodol. was extended to readily available tetracyclic [1,4]thiazepines as well as sulfoxide and sulfone analogs thereof. The reactions resulted in the facile formation of a rare medium-sized [1,4,7]thiazecine ring system that has an emerging utility in bioactive compound design. Comparing the HIRE rates for representative compounds in the three groups of substrates allowed drawing some generalizations about the substituent effects on the course of the reaction.

Journal of Organic Chemistry published new progress about Alkylation. 94087-40-8 belongs to class nitriles-buliding-blocks, and the molecular formula is C7H3ClFN, Synthetic Route of 94087-40-8.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Liu, Chong; Yuan, Jing; Zhang, Zhenfeng; Gridnev, Ilya D.; Zhang, Wanbin published the artcile< Asymmetric Hydroacylation Involving Alkene Isomerization for the Construction of C3-Chirogenic Center>, Recommanded Product: 3-(3-Chlorophenyl)-3-oxopropanenitrile, the main research area is arylcyclopentanone enantioselective preparation; rhodium catalyst enantioselective intramol hydroacylation arylenal alkene isomerization; mechanism transition state energy rhodium catalyzed enantioselective hydroacylation arylenal; alkene isomerization; cycloketones; hydroacylation; rhodacycle; β-H elimination.

A new transformation pattern for enantioselective intramol. hydroacylation has been developed involving an alkene isomerization strategy. Proceeding through a five-membered rhodacycle intermediate, 3-enals such as I (or their Z isomers) were converted to C3- or C3,C5-chirogenic cyclopentanones such as II with satisfactory yields, diastereoselectivities, and enantioselectivities. A catalytic cycle has been theor. calculated and the origin of the stereoselection is rationally explained.

Angewandte Chemie, International Edition published new progress about Cyclopentanones Role: SPN (Synthetic Preparation), PREP (Preparation) (3-aryl-2,2-disubstituted). 21667-62-9 belongs to class nitriles-buliding-blocks, and the molecular formula is C9H6ClNO, Recommanded Product: 3-(3-Chlorophenyl)-3-oxopropanenitrile.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Taldone, Tony; Patel, Pallav D.; Patel, Hardik J.; Chiosis, Gabriela published the artcile< About the reaction of aryl fluorides with sodium sulfide: investigation into the selectivity of substitution of fluorobenzonitriles to yield mercaptobenzonitriles via SNAr displacement of fluorine>, COA of Formula: C7H3ClFN, the main research area is mercaptobenzonitrile synthesis aryl fluoride sulfide substitution.

In this report we describe a simple synthesis of mercaptobenzonitriles from the reaction of fluorobenzonitriles with Na2S in DMF at room temperature and following direct treatment with Zn/HCl. Significantly, 2- and 4-fluorobenzonitriles substituted with chlorine or bromine, but not iodine, undergo selective substitution of fluorine at room temperature to yield synthetically useful halo-substituted mercaptobenzonitriles.

Tetrahedron Letters published new progress about Aromatic substitution reaction. 94087-40-8 belongs to class nitriles-buliding-blocks, and the molecular formula is C7H3ClFN, COA of Formula: C7H3ClFN.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Fache, F.; Cros, F.; Piva, O.; Lefebvre, F. published the artcile< Easy access to 2-alkyl and 2-arylthiazolines using a modified heteropolyacid catalysis: application to the synthesis of bacillamide A>, Synthetic Route of 6136-93-2, the main research area is thiazoline preparation microwave irradiation; aminothiol nitrile cyclization phosphotungstic acid catalyst.

A straightforward access to 2-alkyl and 2-arylthiazolines by condensation of β-aminothiols on nitriles, catalyzed by phosphotungstic acid (2%) under microwave irradiation, is described. This method has been directly applied to a short and efficient synthesis of bacillamide A.

Synthetic Communications published new progress about Heterocyclic compounds Role: SPN (Synthetic Preparation), PREP (Preparation). 6136-93-2 belongs to class nitriles-buliding-blocks, and the molecular formula is C6H11NO2, Synthetic Route of 6136-93-2.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Kaufmann, Julia; Jaeckel, Elisabeth; Haak, Edgar published the artcile< Ruthenium-catalyzed formation of pyrazoles or 3-hydroxynitriles from propargyl alcohols and hydrazines>, Reference of 13635-04-6, the main research area is pyrazole regioselective preparation; hydroxynitrile preparation; propargyl alc hydrazine cascade ruthenium catalyst.

Functionalized pyrazoles I [R = 3-Me, 3-Ph, 5-Me, 5-styryl, etc.] were generated from secondary propargyl alcs. and hydrazines in a ruthenium-catalyzed cascade process, consisting of redox isomerization, Michael addition, cyclocondensation and dehydrogenation steps. The same bifunctional catalyst mediated conversion of tertiary propargyl alcs. with hydrazine to 3-hydroxynitriles II [R1 = Me; R2 = Me, Et, vinyl, etc.] via anti-Markovnikov hydroamination followed by elimination of ammonia was also shown.

ARKIVOC (Gainesville, FL, United States) published new progress about Alcohols, propargyl Role: RCT (Reactant), RACT (Reactant or Reagent). 13635-04-6 belongs to class nitriles-buliding-blocks, and the molecular formula is C5H9NO, Reference of 13635-04-6.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Lai, Miao; Su, Fangyao; Hu, Jingyi; Wang, Mengzhuo; Zhao, Mingqin; Zhang, Ganlin published the artcile< Synthesis of N-heteroarenemethyl esters via C-C bond cleavage of acyl cyanides under transition metal-free conditions>, Recommanded Product: 3-(3-Chlorophenyl)-3-oxopropanenitrile, the main research area is heteroarenemethyl ester acyl cyanide transition metal free condition; C-C bond cleavage; N-heteroaryl esters; N-heteroaryl methanols; acyl cyanides; transition-metal free synthesis.

A practical method to synthesize N-heteroaryl esters from N-heteroaryl methanols with acyl cyanides via C-C bond cleavage without using any transition metal is demonstrated here. The use of Na2CO3/15-crown-5 couple enables access to a series of N-heteroaryl esters in high efficiency. This protocol is operationally simple and highly environmentally benign producing only cyanides as byproducts.

Frontiers in Chemistry (Lausanne, Switzerland) published new progress about C-C bond cleavage. 21667-62-9 belongs to class nitriles-buliding-blocks, and the molecular formula is C9H6ClNO, Recommanded Product: 3-(3-Chlorophenyl)-3-oxopropanenitrile.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Dai, Weixiang; Petersen, Jeffrey L.; Wang, Kung K. published the artcile< Synthesis of the Parent and Substituted Tetracyclic ABCD Ring Cores of Camptothecins via 1-(3-Aryl-2-propynyl)- 1,6-dihydro-6-oxo-2-pyridinecarbonitriles>, Related Products of 89324-17-4, the main research area is camptothecin ABCD ring core preparation nitrogen alkylation Curran’s protocol; intramol hetero Diels Alder acetylene allene rearrangement radical cyclization; radical cyclization reaction mechanism camptothecin core preparation; crystal mol structure indolizinoquinolinone camptothecin ring core analog.

A new synthetic pathway to the parent and substituted ABCD ring cores, e.g. I, of the camptothecin family of alkaloids was developed. The N-alkylation of 1,6-dihydro-6-oxo-2-pyridinecarbonitrile with 3-bromo-1-phenylpropyne provided II using Curran’s protocol. Treatment of II with a catalytic amount of DBU (5 mol %) at 110 °C for 12 h produced indolizino[1,2-b]quinolin-9(11H)-one (I), the parent ABCD ring core of camptothecin, in essentially quant. yield.

Organic Letters published new progress about Alkaloids Role: SPN (Synthetic Preparation), PREP (Preparation). 89324-17-4 belongs to class nitriles-buliding-blocks, and the molecular formula is C6H4N2O, Related Products of 89324-17-4.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts