28561-54-8

Upstream product

• 100-58-3 phenylmagnesium bromide 
• 34161-81-4 5-methyl-2-[(4-methylphenyl)sulfonamido]benzoic acid 
• 2941-78-8 2-Amino-5-methylbenzoic acid 
• 98-59-9 p-toluenesulfonyl chloride 
• 17852-28-7 2-amino-5-methylbenzophenone 

Downstream Products

• 98608-66-3 N-[2-(Hydrazono-phenyl-methyl)-4-methyl-phenyl]-4-methyl-benzenesulfonamide 
• 98608-74-3 C₃₀H₂₈N₆O₂ 
• 98608-78-7 (5E,11E)-3,14-Dimethyl-5,12-diphenyl-7,10,17,20-tetrahydro-6,7,10,11,17,20-hexaaza-dibenzo[a,g]cyclohexadecene-8,9,18,19-tetraone 
• 98608-70-9 C₄₄H₄₀N₆O₆S₂ 
• 1261245-21-9 N-(2-(1-hydroxy-1-phenylbut-3-enyl)-4-methylphenyl)-4-methylbenzenesulfonamide 
• 1334483-36-1 7-methyl-5-phenyl-1-tosyl-2,3-dihydro-1H-benzo[b]azepine 
• 1334483-27-0 1-cyclopropyl-1-(2-(tosylamino)-5-methylphenyl)(phenyl)methanol 
• 1315477-58-7 5-methyl-3-phenyl-1-tosyl-1H-indole-2-carbaldehyde 
• 1315477-41-8 1-(5-methyl-2-(tosylamino)phenyl)-1-phenylprop-2-yn-1-ol 
• 1388038-66-1 5-methyl-3-phenyl-2-(phenylethynyl)-1-tosyl-1H-indole 
• 1448808-69-2 3-(diiodomethyl)-5-methyl-3-phenyl-1-tosylindolin-2-one 
• 1394401-64-9 (Z)-2-benzylidene-5-methyl-3-phenyl-1-tosylindolin-3-ol 

Relevant academic research and scientific papers

Synthesis of15N-labeled heterocyclesviathe cleavage of C-N bonds of anilines and glycine-15N

A nitrogen replacement process that directly incorporates the15N atom of glycine-15N into anilines was reported. The process involves a Csp2-N bond cleavage of anilines driven by dearomatization and a Csp3-N bond cleavage of glycine-15N driven by aromatization. A variety of15N-labeled aromatic heterocycles can be preparedviathis process.

Metal-free synthesis of 1H-indole-2-carbaldehydes by N-iodosuccinimide- mediated cyclization of 1-(2′-anilinyl)prop-2-yn-1-ols in water. A formal synthesis of (R)-calindol

A N-iodosuccinimide (NIS)-mediated method to prepare 1H-indole-2- carbaldehydes efficiently from cycloisomerization of 1-(2-aminophenyl)prop-2-yn- 1-ols is described. The reaction is operationally straightforward and accomplished in good to excellent yiel

1-(2′-Anilinyl)prop-2-yn-1-ol rearrangement for oxindole synthesis

A synthetic method that relies on NIS (N-iodosuccinimide)-mediated cycloisomerization reactions of 1-(2′-anilinyl)prop-2-yn-1-ols to gem-3-(diiodomethyl)indolin-2-ones and 2-(iodomethylene)indolin-3-ones has been developed. The reactions were shown to be chemoselective, with secondary and tertiary alcoholic substrates exclusively giving the 3- and 2-oxindole products, respectively. In the case of the latter, the transformation features an unprecedented double 1,2-OH and 1,2-alkyl migration relay. Density functional theory (DFT) calculations based on proposed iodoaminocyclization species provide insight into this unique divergence in product selectivity. Copyright

Silver triflate catalyzed tandem heterocyclization/alkynylation of 1-((2-tosylamino)aryl)but-2-yne-1,4-diols to 2-alkynyl indoles

Don't cross me! 2-Alkynyl indoles were prepared efficiently by the AgOTf-catalyzed tandem heterocyclization/alkynylation of 1-(2-tosylamino)aryl) but-2-yne-1,4-diols under mild conditions (see scheme). The attractiveness of this approach lies in the fact that both the indole ring and alkyne side chain of the N-heterocycle are sequentially formed from low cost, readily available, and ecologically benign starting materials. It also provides the first route to this synthetically valuable class of compounds that is not based on a cross-coupling strategy. Copyright

Silver acetate catalyzed hydroamination of 1-(2-(sulfonylamino)phenyl)prop- 2-yn-1-ols to (Z)-2-methylene-1-sulfonylindolin-3-ols

A method to prepare (Z)-2-methylene-1-sulfonylindolin-3-ols efficiently that relies on silver acetate catalyzed hydroamination of 1-(2-(sulfonylamino) phenyl)prop-2-yn-1-ols is reported. The reactions proceed rapidly at room temperature with catalyst loadings as low as 1 mol % under conditions that did not require the exclusion of air or moisture. The utility of this N-heterocyclic ring-forming strategy as a synthetic tool that makes use of unsaturated alcohols was exemplified by the conversion of the (Z)-2-methylene-1- sulfonylindolin-3-ol to examples of other members of the indole family of compounds.

Cyclopropyl carbinol rearrangement for benzo-fused nitrogen ring synthesis

A synthetic method that relies on gold-catalysed cyclopropyl carbinol rearrangement of 2-tosylaminophenyl cyclopropylmethanols to prepare 2,3-dihydro-1H-benzo[b]azepines and 2-vinylindolines efficiently is reported. The reactions were shown to be chemoselective, with secondary and tertiary alcohol substrates exclusively providing benzo-fused five- and seven-membered ring products, respectively. The ring-forming process was also found to proceed in moderate to excellent yields under mild conditions only in the presence of the gold and silver catalyst combination. The mechanism is thought to involve activation of the alcohol by the (p-CF3C6H 4)3PAuCl/AgOTf (Tf=triflate) catalyst, resulting in ionization of the starting material. The tertiary carbocationic intermediate generated in situ in this manner then triggers ring-opening of the cyclopropane moiety and trapping by the tethered aniline group to give the 2,3-dihydro-1H-benzo[b]azepine. Cyclopropane ring fragmentation of the secondary carbocationic analogue, on the other hand, results in diene formation followed by subsequent intramolecular hydroamination to afford the 2-vinylindoline. Copyright

Gold-catalyzed cycloisomerizations of 1-(2-(Tosylamino)phenyl)prop-2-yn-1- ols to 1H-Indole-2-carbaldehydes and (E)-2-(Iodomethylene)Indolin-3-ols

A method to prepare lH-indole-2-carbaldehydes and (E)-2-(iodomethylene) indolin-3-ols by gold(I)-catalyzed cycloisomerization of l-(2-(tosylamino) phenyl)prop-2-yn-1-ols with N-iodosuccinimide (NIS) is reported. The reactions were shown to be operationally simplistic and proceed efficiently for a wide variety of substrates, affording the corresponding products in good to excellent yields (70-99%). The mechanism is suggested to involve activation of the alkyne moiety of the substrate by the gold(I) catalyst. This triggers intramolecular addition of the tethered aniline moiety to give a vinyl gold intermediate, which undergoes iododeauration with NIS to give the (E)-2-(iodomethylene)indolin-3-ol adduct. Subsequent 1,3-allylic alcohol isomerization (1,3-AAI) followed by formylation of this vinyl iodide intermediate then gives the 1H-indole-2-carbaldehyde.

Copper(II) triflate-catalyzed intramolecular hydroamination of homoallylic amino alcohols as an expedient route to trans-2,5-dihydro-1H-pyrroles and 1,2-dihydroquinolines

A new efficient synthetic route to trans-2,5-dihydro-1H-pyrroles and 1,2-dihydroquinolines that relies on copper(II) triflate-catalyzed intramolecular hydroamination of homoallylic amino alcohols under mild and operationally straightforward conditions is