153633-36-4

Upstream product

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

Downstream Products

• 1417815-06-5 2-phenylindeno[2,1-b]pyrrol-8(1H)-one 
• 1417814-99-3 C₂₄H₁₈BrNO₃S 
• 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 
• 914458-46-1 2-phenyl-4-(1-naphthoyl)-N-p-toluenesulfonylpyrrole 
• 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

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.

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 %.

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.