153633-36-4

Upstream product

• 153633-38-6 3-phenyl-2-(toluene-4-sulfonyl)-3,6-dihydro-2H-[1,2]thiazine 1-oxide 
• 290306-56-8 2-bromo-1-(p-toluenesulfonyl)pyrrole 
• 98-80-6 phenylboronic acid 
• 3042-22-6 2-phenyl-1H-pyrrole 
• 98-59-9 p-toluenesulfonyl chloride 
• 16939-57-4 (E)-buta-1,3-dienylbenzene 
• 17639-64-4 N-p-toluenesulfonylpyrrole 
• 591-50-4 iodobenzene 
• 1190987-87-1 N-(2-hydroxy-4-phenylbut-3-ynyl)-4-methylbenzenesulfonamide 
• 209980-92-7 C₂₀H₂₃NO₂SSi 
• 4104-47-6 N-sulfinyl-p-toluenesulfonamide 
• 613-91-2 acetophenone oxime 

Downstream Products

• 914458-46-1 2-phenyl-4-(1-naphthoyl)-N-p-toluenesulfonylpyrrole 
• 1417814-99-3 C₂₄H₁₈BrNO₃S 
• 1417815-06-5 2-phenylindeno[2,1-b]pyrrol-8(1H)-one 
• 1239984-61-2 ethyl 4-oxo-4-(5'-phenyl-N-tosyl-2'-pyrrolyl)butanoate 
• 914458-21-2 (1-heptyl-5-phenyl-1H-pyrrol-3-yl)-1-naphthalenylmethanone 
• 914458-20-1 (1-hexyl-5-phenyl-1H-pyrrol-3-yl)-1-naphthalenylmethanone 
• 914458-48-3 naphthalen-1-yl(5-phenyl-1H-pyrrol-3-yl)methanone 
• 3042-22-6 2-phenyl-1H-pyrrole 

Relevant academic research and scientific papers

Integration of oxidative arylation with sulfonyl migration: One-pot tandem synthesis of densely functionalized (NH)-pyrroles

A one-pot synthesis of 2-aryl-3-alkyl/aryl-sulfonyl-(NH)-pyrroles from N-sulfonylpyrroles, developed for the first time, via palladium-catalyzed oxidative C-2 arylation followed by sulfonyl migration is described. The simple, easy access to the highly functionalized free-NH pyrroles secures opportunities for the preparation of compounds with promising biological activities in contemporary organic synthesis. The event of sulfonyl migration from pyrrole-N to C-3 is thermodynamically favored as revealed by density functional methods. The different plausible mechanisms for the migration of the sulfonyl group are also discussed.

Magnesiation of N-Heterocycles Using i-PrMgCl · LiCl and catalytic diisopropylamine

The direct magnesiation of various N-heterocyclic compounds with i-PrMgCl · LiCl and catalytic diisopropylamine allows for preparation of 2-substituted pyrroles, imidazole, indoles, and benzimidazoles, in moderate to good yields. The magnesiated substrates canreadily undergo a Kumada-type coupling with iodo-aryls in the presence of catalytic Pd(PPh3)4.

An efficient and selective synthesis of 2,5-substituted pyrroles by gold-catalysed ring expansion of alkynyl aziridines

A range of substituted alkynyl aziridines undergo a ring expansion to afford 2,5-substituted pyrroles under gold catalysis. While effective conditions can be generated from other gold sources, a combination of Ph3PAuCl and AgOTs generate a cata

An extremely facile synthesis of furans, pyrroles, and thiophenes by the dehydrative cyclization of propargyl alcohols

Furans, pyrroles, and thiophenes are efficiently prepared by gold-catalyzed dehydrative cyclizations of readily available, heteroatom-substituted propargyllc alcohols. The reactions are rapid, high-yielding, and procedurally simple, giving essentially pure aromatic heterocycles In minutes under open-flask conditions with catalyst loadings as low as 0.05 mol %.

A facile and regioselective synthesis of 2,5-disubstituted pyrroles via gold-catalyzed cycloisomerization of acetylenylaziridines

Gold-catalyzed cycloisomerization reaction of acetylenylaziridines provides 2,5-disubstituted pyrroles in high yields. The presence of protic species accelerates the reaction rate and improves the yields of pyrrole products.

1-Alkyl-2-aryl-4-(1-naphthoyl)pyrroles: New high affinity ligands for the cannabinoid CB1 and CB2 receptors

Two series of 1-alkyl-2-aryl-4-(1-naphthoyl)pyrroles were synthesized and their affinities for the cannabinoid CB1 and CB2 receptors were determined. In the 2-phenyl series (5) the N-alkyl group was varied from n-propyl to n-heptyl. A second series of 23 1-pentyl-2-aryl-4-(1-naphthoyl)-pyrroles (6) was also prepared. Several compounds in both series have CB1 receptor affinities in the 6-30 nM range. The high affinities of these pyrrole derivatives relative to JWH-030 (1, R = C5H11) support the hypothesis that these pyrroles interact with the CB1 receptor primarily by aromatic stacking.

2-Bromo-N-(p-toluenesulfonyl)pyrrole: A Robust Derivative of 2-Bromopyrrole

2-Bromo-AL(p-toluenesulfonyl)pyrrole (2), a crystalline stable derivative of 2-bromopyrrole (1) has been prepared in 80% yield by bromination of pyrrole, followed by conversion to the N-(p-toluenesulfonyl) derivative. This compound is stable indefinitely at ambient temperature. Compound 2 is an excellent substrate for Suzuki coupling with arylboronic acids.

N-p-Toluenesulfonylpyrroles from 1,3-dienes

1,3-Dienes can be converted to N-p-toluenesulfonylpyrroles in two steps: 1) [4+2]-cycloaddition with N-sulfinyl-p-toluenesulfonamide and 2) conversion of the 3,6-dihydro-1,2-thiazine oxide adduct to a pyrrole using triethylamine-trimethylphosphite.