34159-05-2

Usage

InChI:InChI=1/C14H12BrNO3S/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

• 6590-65-4 N-(2-Formyl-phenyl)-4-methyl-benzenesulfonamide 
• 223526-84-9 methyl 5-bromo-2-{[(4-methylphenyl)sulfonyl]amino}benzoate 
• 70-55-3 toluene-4-sulfonamide 
• 93777-26-5 5-bromo-2-fluorobenzaldehyde 
• 329281-02-9 N-(4-bromo-2-(hydroxymethyl)phenyl)-4-methylbenzenesulfonamide 
• 20712-12-3 (2-amino-5-bromophenyl)methanol 
• 941-55-9 4-toluenesulfonyl azide 
• 1241894-37-0 5-bromo-2-nitrobenzylic alcohol 
• 20357-20-4 5-bromo-2-nitrobenzaldehyde 
• 98-59-9 p-toluenesulfonyl chloride 
• 31100-21-7 5-bromo-2-[(4-methylphenyl)sulfonamido]benzoic acid 
• 5794-88-7 5-Bromo-2-aminobenzoic acid 
• 52727-57-8 5-bromo-2-aminobenzoic acid methyl ester 
• 90312-02-0 N-(2-hydroxymethylphenyl)-4-methylbenzenesulfonamide 

Downstream Products

• 943819-82-7 ethyl 4-{(4-bromo-2-formylphenyl)[(4-methylphenyl)sulfonyl]amino}butanoate 
• 1242061-56-8 C₂₈H₂₉BrN₂O₂S 
• 1242061-58-0 C₂₇H₃₇BrN₂O₄SSi 
• 1242061-54-6 C₂₆H₂₅BrN₂O₃S 
• 1242061-57-9 C₂₂H₂₅BrN₂O₄S 
• 1448809-05-9 5-bromo-2-(iodomethylene)-1-tosylindolin-3-one 
• 1448808-96-5 1-(5-bromo-2-(tosylamino)phenyl)prop-2-yn-1-ol 
• 1439384-18-5 N-(4-bromo-2-formylphenyl)-4-methyl-N-(prop-2-yn-1-yl)benzenesulfonamide 
• 1439383-86-4 7-bromo-1-tosyl-1H-benzo[b]azepin-3(2H)-one 
• 1613505-51-3 C₂₄H₁₈BrNO₃S 
• 1613505-73-9 C₁₇H₁₆BrNO₃S 
• 1619985-38-4 2-((2S,3R,4S)-6-bromo-1,2,3,4-tetrahydro-3-nitro-2-phenyl-1-tosylquinolin-4-yl)-1-phenylethanone 
• 1619985-52-2 (E)-3-(5-bromo-2-(tosylamino)phenyl)-1-phenylprop-2-en-1-one 

Relevant academic research and scientific papers

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.

Direct Access to 9-Chloro-1 H-benzo[ b]furo[3,4- e]azepin-1-ones via Palladium(II)-Catalyzed Intramolecular syn-Oxypalladation/Olefin Insertion/sp2-C-H Bond Activation Cascade

An efficient Pd(II)-catalyzed cascade approach was established for the synthesis of 9-chloro-1H-benzo[b]furo[3,4-e]azepin-1-ones starting from N-propargyl arylamines having a pendant α,β-unsaturated ester scaffold. The mechanism of this sequential process involved intramolecular syn-oxypalladation followed by olefin insertion and ortho sp2-C-Cl bond formation reactions. This high atom- and step-economical cascade sequence generated two heterocycle rings and three new bonds in a single synthetic operation.

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

Palladium-catalyzed oxidative cyclization of aniline-tethered alkylidenecyclopropanes with O2: a facile protocol to selectively synthesize 2- and 3-vinylindoles

A novel palladium-catalyzed oxidative cyclization of aniline-tethered alkylidenecyclopropanes using molecular oxygen as the terminal oxidant through β-carbon elimination of aminopalladation intermediates is disclosed. The reaction opens up an effective way to obtain a series of 2- and 3-vinylindoles which are important synthetic intermediates in many natural indole derivatives.

Iridium-Catalyzed Direct ortho-C-H Amidation of Benzaldehydes through N-Sulfonyl Imines as Mask

Ir-catalyzed direct C-H sulfamidation of benzaldehydes has been achieved. A series of ortho-amided benzaldehydes were obtained in up to 95% yields for 21 examples with excellent regioselectivity and broad functional group tolerance. This transformation could proceed smoothly with low catalyst loading under external-oxidant-, acid-, or base-free conditions. Molecular nitrogen was released as the sole byproduct, providing an environmentally benign sulfamidation process.

Rhodium(iii)-catalyzed coupling of N-sulfonyl 2-aminobenzaldehydes with oxygenated allylic olefins through C-H activation

Rh(iii)-catalyzed coupling of N-sulfonyl 2-aminobenzaldehydes with oxygenated allylic olefins via C-H bond activation is described. Diarylketones were obtained through coupling of N-sulfonyl 2-aminobenzaldehydes with 7-oxabenzonorbornadienes. On the other

Asymmetric domino aza-Michael-Michael reaction of o-N-protected aminophenyl α,β-unsaturated ketones: Construction of chiral functionalized tetrahydroquinolines

The diastereo- and enantioselective synthesis of 2,3,4-trisubstituted tetrahydroquinolines has been developed through organocatalytic domino aza-Michael-Michael reaction of o-N-tosylaminophenyl α,β-unsaturated ketones with nitroalkenes. This useful and simple domino process afforded diverse highly functionalized tetrahydroquinolines, some of which are not easily accessible using other methodologies, in good yields and with excellent diastereo- and enantioselectivities (up to >30:1 dr, >99% ee).