34159-03-0

Usage

InChI:InChI=1/C14H12ClNO3S/c1-10-2-5-13(6-3-10)20(18,19)16-14-7-4-12(15)8-11(14)9-17/h2-9,16H,1H3

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 941-55-9 4-toluenesulfonyl azide 
• 587-04-2 m-Chlorobenzaldehyde 
• 6628-86-0 5-chloro-2-nitrobenzaldehyde 
• 73033-58-6 5-chloro-2-nitrobenzyl alcohol 
• 37585-25-4 2-amino-5-chlorobenzyl alcohol 
• 635-21-2 5-chloroanthranilic acid 
• 247237-38-3 N-p-toluenesulfonyl-5-chloro-anthranilic acid methyl ester 
• 5202-89-1 4-chlorobenzenesulfonyl chloride 
• 675578-47-9 N-(4-chloro-2-(hydroxymethyl)phenyl)-4-methylbenzenesulfonamide 

Downstream Products

• 169263-30-3 4-chloro-2-(hydroxy(phenyl)methyl)-1-(4-methylphenylsulfonamido)benzene 

Relevant academic research and scientific papers

Intramolecular Umpolung Allylation of Imines

An intramolecular umpolung allylation of imines is reported. This reaction occurs via the intermediacy of 2-azaallyl anions. It could proceed either under transition-metal-catalyzed conditions or under transition-metal-free conditions. Importantly, this a

Copper-Catalyzed (4+1) Cascade Annulation of Terminal Alkynes with 2-(Tosylmethyl)anilines: Synthesis of 2,3-Disubstituted Indoles

A novel strategy based on Cu-catalyzed (4+1) cascade annulation of terminal alkynes as one-carbon synthons with 2-(tosylmethyl)anilines has been developed for the expeditious synthesis of 2,3-disubstituted indoles, in which in situ generations of aza-o-quinone methides and alkynyl-copper(I) species are involved. This annulation provides an effective method for the assembly of synthetically and structurally interesting 2,3-disubstituted indoles.

Diastereoselective Construction of Cyclopropane-Fused Tetrahydroquinolines via a Sequential [4 + 2]/[2 + 1] Annulation Reaction

A sequential [4 + 2]/[2 + 1] annulation of α-aryl vinylsulfoniums with 2-aminochalcones and 2-(2-aminobenzylidene)-1H-indene-1,3(2H)-dione is reported that affords a series of cyclopropane-fused tetrahydroquinolines. The salient features of this novel and practical transformation include high efficiency, transition-metal-free nature, operational simplicity, and outstanding functional group tolerance.

Benzoazepine-Fused Isoindolines via Intramolecular (3 + 2)-Cycloadditions of Azomethine Ylides with Dinitroarenes

Aminobenzaldehydes bearing a pendant 3,5-dinitrophenyl group react thermally with N-substituted α-amino acids to form unprecedented benzoazepine-fused isoindolines. The reaction proceeds via a dearomatization/rearomatization sequence involving an intramolecular (3 + 2)-cycloaddition between the in situ formed azomethine ylide and the dinitroarene. Various glycine derivatives are tolerated as well as branched substrates based on cyclic, α-mono-, and α,α-disubstituted amino acids, giving single diastereomers in many cases. The method is scalable and gives products with a nitro group ready for further manipulation.

Palladium-Catalyzed Regioselective Syn-Chloropalladation-Olefin Insertion-Oxidative Chlorination Cascade: Synthesis of Dichlorinated Tetrahydroquinolines

A palladium catalyzed cascade process involving syn-chloropalladation, intramolecular olefin insertion, and oxidative C-Cl bond formation reactions was demonstrated for the synthesis of dichlorinated tetrahydroquinolines in high yields (up to 93%). The N-propargyl arylamines having a tethered α,β-unsaturated carbonyl moiety underwent a regioselective syn-chloropalladation followed by a Heck-type reaction to deliver the tetrahydroquinoline scaffold. The rare insertion of the second chlorine atom was rationalized comprising a PdII/IV catalytic cycle and oxidative cleavage of the C-PdII bond.

A nickel(ii)-catalyzed asymmetric intramolecular Alder-ene reaction of 1,7-dienes

A highly diastereo- and enantioselective intramolecular Alder-ene reaction with an alkene as the enophile has been developed by using a chiral N,N′-dioxide/nickel(ii) complex as the catalyst. This protocol provides a facile route towards the synthesis of diverse 3,4-disubstituted chroman, tetrahydroquinoline, piperidine and thiochroman derivatives in high yields with good to excellent diastereo- and enantioselectivities.

Asymmetric [4+2] cycloaddition of azlactones with dipolar copper–allenylidene intermediates for chiral 3,4-dhydroquinolin-2-one derivatives

In this paper, a pybox-copper catalyzed enantioselective decarboxylative [4+2] cycloaddition reaction of ethynyl benzoxazinanones with azlactones has been developed, which provides optically active 3,4-dihydroquinolin-2-ones in high yields with good enantioselectivities and diastereoselectivities. In this transformation, the chiral dipolar copper–allenylidene intermediates are kinetically generated via decarboxylative ethynyl benzoxazinanones, followed by the attack of the enolate azlactones to form enantiomerically enriched 3,4-dihydroquinolin-2-one structures.

Iridium- and Rhodium-Catalyzed Directed C-H Heteroarylation of Benzaldehydes with Benziodoxolone Hypervalent Iodine Reagents

The C-H heteroarylation of benzaldehydes with indoles and pyrroles was realized using the benziodoxolone hypervalent iodine reagents indole- and pyrroleBX. Functionalization of the aldehyde C-H bond using either an o-hydroxy or amino directing group and catalyzed by an iridium or a rhodium complex allowed the synthesis of salicyloylindoles and (2-sulfonamino)benzoylindoles, respectively, with good to excellent yields (74-98%). This new transformation could be carried out under mild conditions (rt to 40 °C) and tolerated a broad range of functionalities, such as ethers, halogens, carbonyls, or nitro groups.

Amphoteric 2-(sulfonylamino)benzaldehydes, secondary amines and isocyanides in the multicomponent synthesis of elusive N-alkyl-2,3-diaminoindoles

A novel interrupted Ugi reaction between ortho-sulfonylaminated aryl aldehydes, secondary amines, and isocyanides affords in good to high yields N-alkyl-2,3-diaminoindoles, providing access to a so far unexplored area of the indole chemical space. With only one single chemical operation, this novel reaction affords a broad gamma of substituted 2,3-diaminoindoles with five points of diversity. The success of this novel multicomponent transformation lies in presence of the amphoteric sulfonylamino group, which sequentially acts as a Br?nsted acids and as a nucleophile the lack of need for additional catalysts and the high atom economy, with the loss of only one molecule of water, renders this approach a very effective one.

Direct stereoselective construction of cyclopropane α-amino acid with contiguous quaternary centers via [4 + 2] annulation reaction

A direct diastereoselective synthetic approach to useful cyclopropane α-amino acid was established via base-promoted [4 + 2] annulations between o-aminobenzaldehydes and alkyl 2-aroyl-1-chlorocyclopropanecarboxylates. The annulation reaction proceeded quickly under mildly basic conditions, affording α-aminocyclopropanecarboxylic acid derivatives in moderate to excellent yields with high diastereoselectivities (up to 19 : 1).