Day: November 15, 2022

Rae, James published the artcileSynthesis of Axially Chiral C-N Scaffolds via Asymmetric Coupling with Enantiopure Sulfinyl Iodanes, Recommanded Product: 4-Chloroindoline, the main research area is copper catalyzed atropselective coupling chiral iodane sulfoxide auxiliary; axially chiral carbon nitrogen scaffold synthesis.

Axially chiral C-N compounds are an emerging but scarcely investigated class of stereogenic mols. with potential applications as biol. active scaffolds and chiral ligands. The synthesis of these compounds is extremely challenging, and in particular, no metal-catalyzed asym., intermol. C-N coupling has been previously reported. Herein we disclose an intermol. atropselective C-N coupling, occurring with excellent stereoselectivity. This Cu-catalyzed transformation is based on the use of highly active coupling partners (i.e., chiral iodanes bearing a very cheap and traceless sulfoxide auxiliary). Use of such original ortho-sulfoxide iodanes enables this unprecedented coupling to occur at room temperature, guaranteeing high atropselectivity and atropselectivity of the coupling products under reaction conditions. Because of extensive possible postmodifications of the optically pure products, a panel of C-N axially chiral scaffolds can now be accessed.

ACS Catalysis published new progress about Anion exchange (of sulfoxide iodanes). 41910-64-9 belongs to class indole-building-block, name is 4-Chloroindoline, and the molecular formula is C8H8ClN, Recommanded Product: 4-Chloroindoline.

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

James, C. S. published the artcilePlant growth-regulating substances. XXVI. Isatic and anthranilic acids, HPLC of Formula: 1677-47-0, the main research area is isatic acid growth regulation; anthranilic acid growth regulation; growth regulation anthranilic acid.

The plant growth-regulating activities of isatic acid and 26 isatic acid derivatives, together with the 27 corresponding anthranilic acids, were assessed in the wheat cylinder, the pea segment, and pea curvature tests. Activity was sustained by substitution in the 4-and 5-positions of isatic acid as in Na 4-chloroisatate and Na 5-bromoisatate but decreased by substitution in the 3- and 6-positions as in Na 3-chloroisatate and Na 6-chloroisatate. In the anthranilic acid series, the parent acid was inactive but the introduction of a large grouping (Br or I) into the 5-position as in Na 5-iodoanthranilate conferred activity. The 3,6- and 5,6-dichloro and the 3,6-dibromo acids such as Na 3,6-dichloroisatate were also active; compounds substituted in the 4-position to the carboxyl group or disubstituted in the 3 and 5 positions as in Na 3,5-dichloroisatate, were, as expected, inactive. Wheat coleoptile and pea stem segments metabolized Na isatate and Na 5-chloroisatate to the corresponding Na anthranilate and Na 5-chloroanthranilate, together with an unidentified nonacidic metabolite in each case. The acids apparently possess activity per se since there was no evidence that the growth regulating activity of isatic acids was related to this breakdown. 19 references.

Annals of Applied Biology published new progress about Hormones, plant Role: BIOL (Biological Study). 1677-47-0 belongs to class indole-building-block, name is 4,5-Dichloroisatin, and the molecular formula is C8H3Cl2NO2, HPLC of Formula: 1677-47-0.

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Qin, Jingyang published the artcileCatalytic Atroposelective Electrophilic Amination of Indoles, Name: 2-(tert-Butyl)-5-chloro-1H-indole, the main research area is sulfonyl arylaminoindole preparation enantioselective chemoselective anticancer activity DFT; Amination; Atroposelectivity; Conjugation; C−N Axis; Heterocycles.

The first catalytic atroposelective electrophilic amination of indoles I (R = 2-t-Bu, 4-Me, 5-Ph), which delivers functionalized atropochiral N-sulfonyl-3-arylaminoindoles II (R1 = Boc, (4-methylphenyl)sulfonyl, (1-naphthyl)sulfonyl, etc.) with excellent optical purity was reported. This reaction was furnished by 1,6-nucleophilic addition to p-quinone diimines III. Control experiments suggest an ionic mechanism that differs from the radical addition pathway commonly proposed for 1,6-addition to quinone III (R1 = (4-methylphenyl)sulfonyl). The origin of 1,6-addition selectivity was investigated through computational studies. Preliminary studies show that the obtained 3-aminoindoles atropisomers II exhibit anticancer activities. This method was valuable with respect to enlarging the toolbox for atropochiral amine derivatives II.

Angewandte Chemie, International Edition published new progress about Amination catalysts (chemo-, stereoselective). 69622-40-8 belongs to class indole-building-block, name is 2-(tert-Butyl)-5-chloro-1H-indole, and the molecular formula is C12H14ClN, Name: 2-(tert-Butyl)-5-chloro-1H-indole.

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Yang, Yurong published the artcileRu(II)-Catalyzed and acidity-controlled tunable [5+1]/[5+2] annulation for building ring-fused quinazolines and 1,3-benzodiazepines, Product Details of C8H8ClN, the main research area is indolyl benzimidazole preparation propargyl carbonate ruthenium catalyst regioselective cycloaddition; isobutenyl benzoimidazopyrroloquinazoline preparation; alkenyl benzoimidazodiazepinoindole preparation.

The Ru(II)-catalyzed tunable [5+1]/[5+2] annulation of N-benzo[d]imidazole indolines with propargyl carbonates was realized for the divergent synthesis of ring-fused quinazolines and 1,3-benzodiazepines bearing various functional groups. These transformations represented an efficient and practical strategy in constructing complex heterocycles via diversified C-H functionalization. A distinctive acidity-controlled reaction manner was clarified to account for the chemoselectivity.

Chemical Communications (Cambridge, United Kingdom) published new progress about [5+2] Cycloaddition reaction (regioselective). 41910-64-9 belongs to class indole-building-block, name is 4-Chloroindoline, and the molecular formula is C8H8ClN, Product Details of C8H8ClN.

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Xiao, Jun-An published the artcileGold/scandium bimetallic relay catalysis of formal [5+2]- and [4+2]-annulations: access to tetracyclic indole scaffolds, SDS of cas: 13523-93-8, the main research area is alkynylaryl cyclopropane diester indole gold scandium catalyst regioselective cycloaddition; dimethyl dihydrobenzocycloheptaindolyl methylmalonate preparation; ethynylphenyl cyclopropane dicarboxylate indole gold scandium catalyst regioselective cycloaddition; dimethylbenzocarbazolyl methyl dimethylmalonate preparation.

Regiodivergent formal [5+2]- and [4+2]-annulation reactions of indole derivatives with 2-(2-alkynyl)aryl cyclopropane-1,1-diesters (ACPs) was developed. A series of tetracyclic indole derivatives were delivered in a 77% average yield with excellent regioselectivities enabled by Au(I)/Sc(III) bimetallic relay catalysis. A gram-scale reaction and further transformation of the resulting tetracyclic indoles demonstrated the practical utility of this protocol. Moreover, the photophys. properties of the obtained multicyclic compounds were also investigated.

Chemical Communications (Cambridge, United Kingdom) published new progress about [4+2] Cycloaddition reaction (regioselective). 13523-93-8 belongs to class indole-building-block, name is 4-(Benzyloxy)-1-methyl-1H-indole, and the molecular formula is C16H15NO, SDS of cas: 13523-93-8.

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Chen, Ye-Hui published the artcileOrganocatalytic Enantioselective Synthesis of Atropisomeric Aryl-p-Quinones: Platform Molecules for Diversity-Oriented Synthesis of Biaryldiols, Application of 2-(tert-Butyl)-5-chloro-1H-indole, the main research area is aryl quinone enantioselective preparation organocatalyst diversity oriented biaryldiol; atropisomerism; biaryls; chirality; organocatalysis; quinones.

Presented here is a class of novel axially chiral aryl-p-quinones as platform mols. for the preparation of non-C2 sym. biaryldiols. Two sets of aryl-p-quinone frameworks were synthesized with remarkable enantiocontrol by chiral phosphoric acid catalyzed enantioselective arylation of p-quinones by central-to-axial chirality conversion. These aryl-p-quinones were then used to access a wide spectrum of highly functionalized non-C2 sym. biaryldiols with excellent retention of the enantiopurity.

Angewandte Chemie, International Edition published new progress about Arylation catalysts, stereoselective (oxidative). 69622-40-8 belongs to class indole-building-block, name is 2-(tert-Butyl)-5-chloro-1H-indole, and the molecular formula is C12H14ClN, Application of 2-(tert-Butyl)-5-chloro-1H-indole.

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Chen, Qing-An published the artcileRhodium-Catalyzed Enantioselective Hydroamination of Alkynes with Indolines, Computed Properties of 41910-64-9, the main research area is rhodium catalyst regioselective stereoselective hydroamination alkyne indoline; branched allylic indoline preparation.

The hydroamination of internal alkynes via tandem rhodium catalysis gives branched N-allylic indolines with high regio- and enantioselectivity. An acid switch provides access to the linear isomer in preference to the branched isomer by an isomerization mechanism. Mechanistic studies suggest formation of an allene intermediate, which undergoes hydroamination to generate allylic amines instead of the enamine or imine products typically observed in alkyne hydroaminations.

Journal of the American Chemical Society published new progress about Alkynes Role: RCT (Reactant), RACT (Reactant or Reagent). 41910-64-9 belongs to class indole-building-block, name is 4-Chloroindoline, and the molecular formula is C8H8ClN, Computed Properties of 41910-64-9.

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Zhang, Li published the artcileRu-Catalyzed selective C-H oxidative olefination with N-heteroarenes directed by pivaloyl amide, Synthetic Route of 41910-64-9, the main research area is indoline alkylaniline pivaloyl amide oxidative olefination regioselective ruthenium catalyst.

A highly efficient and practical Ru-catalyzed direct C-H functionalization of indolines and N-alkylaniline with a simple pivaloyl as a directing group is developed. Broad substrate scopes with respect to N-heteroarenes and olefins are observed The selective C7-position alkynylation for indoline also proceeds well by using inexpensive ruthenium as a catalyst, and pivaloyl as a directing group.

Organic Chemistry Frontiers published new progress about Alkenes Role: RCT (Reactant), RACT (Reactant or Reagent). 41910-64-9 belongs to class indole-building-block, name is 4-Chloroindoline, and the molecular formula is C8H8ClN, Synthetic Route of 41910-64-9.

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Zhou, Tao published the artcileRh(III)-Catalyzed Carbocyclization of 3-(Indolin-1-yl)-3-oxopropanenitriles with Alkynes and Alkenes through C-H Activation, Recommanded Product: 4-Chloroindoline, the main research area is indoline stereoselective regioselective preparation rhodium catalyst reaction mechanism; alkyne alkene indoline carbocyclization.

Rh(III)-catalyzed carbocyclization reactions of 3-(indolin-1-yl)-3-oxopropanenitriles with alkynes and alkenes have been developed to form 1,7-fused indolines through C-H activation. These reactions have a broad range of substrates and high yields. Unsym. aryl-alkyl substituted alkynes proceeded smoothly with high regioselectivity. Electron-rich alkynes could undergo further oxidative coupling reaction to form polycyclic compounds For alkenes, 1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-4-ones were formed via C(sp2)-H bond alkenylation and C(sp2)-H, C(sp3)-H oxidative coupling reactions.

Organic Letters published new progress about Alkenes Role: RCT (Reactant), RACT (Reactant or Reagent). 41910-64-9 belongs to class indole-building-block, name is 4-Chloroindoline, and the molecular formula is C8H8ClN, Recommanded Product: 4-Chloroindoline.

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Ma, Rui-Jun published the artcileSynthesis of dihydro-[1,3]oxazino[4,3-a] isoindole and tetrahydroisoquinoline through Cu(OTf)2-catalyzed reactions of N-acyliminium ions with ynamides, Application of 5-Chloroisoindolin-1-one, the main research area is isoindole acetal ynamide copper catalyst cyclization; dihydrooxazinoisoindole preparation; tetrahydroisoquinoline acetal ynamide copper catalyst cyclization; dihydrooxazinoisoquinolinone preparation.

An efficient approach to access functionalized dihydro-[1,3]oxazino[4,3-a] isoindole and tetrahydroisoquinoline skeletons has been developed through the addition-cyclization process of ynamides with N-acyliminium ions generated from N,O-acetals. The reactions were conducted under the catalysis of Cu(OTf)2, and a number of functionalized dihydro-[1,3]oxazino[4,3-a] isoindoles and tetrahydroisoquinolines were generated in 48-98% yields. When chiral ynamides were used, optically pure tetrahydroisoquinolines could be obtained with good to excellent yields and diastereoselectivities.

Tetrahedron Letters published new progress about Acetals Role: RCT (Reactant), RACT (Reactant or Reagent). 74572-29-5 belongs to class indole-building-block, name is 5-Chloroisoindolin-1-one, and the molecular formula is C8H6ClNO, Application of 5-Chloroisoindolin-1-one.

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles