102619-06-7

Upstream product

• 1003-29-8 2-pyrrole aldehyde 
• 98-59-9 p-toluenesulfonyl chloride 
• 17639-64-4 N-p-toluenesulfonylpyrrole 
• 123892-38-6 1-(methylsulfonyl)-1H-pyrrole-2-carbaldehyde 
• 102619-05-6 1-(toluene-4-sulfonyl)-1H-pyrrole-2-carbaldehyde 
• 216171-18-5 2-chloromethyl-1-methanesulfonyl-1H-pyrrole 
• 202580-86-7 (1-methanesulfonyl-1H-pyrrol-2-yl)methanol 

Downstream Products

• 102619-07-8 1-(4-Methylphenylsulfonyl)-2-<(2-propinyloxy)methyl>pyrrol 
• 1188297-06-4 N-[4-(4-methoxyphenoxy)-2-methylbut-3-yn-2-yl]-4-methyl-N-[(1-tosyl-1H-pyrrol-2-yl)methyl]benzenesulfonamide 

Relevant academic research and scientific papers

Pd-catalyzed allylative dearomatisation using Grignard reagents

Pd-catalyzed allylative dearomatisation of naphthyl halides is shown to be feasible by employing Grignard reagents. The high reactivity of the nucleophile allows for fast reactions and low catalyst loading, while a plethora of successfully substituted compounds illustrate the broad scope. Five membered heteroaromatic compounds are also demonstrated to be reactive under similar conditions.

Proton-exchanged montmorillonite-mediated reactions of hetero-benzyl acetates: Application to the synthesis of Zafirlukast

Proton-exchanged montmorillonite (H-mont) with outstanding surface characteristics can provide abundant acidic sites in the mesopores, and serve as an efficient heterogeneous catalyst for the synthesis of heterocycle-containing diarylmethanes via Friedel-Crafts-like alkylation of (hetero)arenes by heterobenzyl acetates under mild reaction conditions without requiring any additives or an inert atmosphere. Using this strategy, the gram-scale synthesis of indole-containing diarylmethane 13 has been accomplished in good yield for the preparation of Zafirlukast. In addition, H-mont can be applied to the nucleophilic substitution reactions of heterobenzyl acetate 5p with a variety of alcohols and 1,3-dicarbonyl compounds.

Rh(II)-Catalyzed Monocyclopropanation of Pyrroles and Its Application to the Synthesis Pharmaceutically Relevant Compounds

Here we report Rh(II)-catalyzed monocyclopropanation reactions on pyrroles in the presence of aryldiazoacetates, providing the corresponding dearomatized products with high levels of enantioselectivity (up to >99% ee). Under the catalysis of Rh2/sub

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.

Palladium-catalyzed regioselective allylation of five-membered heteroarenes with allyltributylstannane

Palladium-catalyzed allylation reactions of 2-(chloromethyl)thiophenes, 2-(chloromethyl)furans, and N-protected 2-(chloromethyl)-1H-pyrroles with allyltributylstannane were described in this study. This type of allylation reaction regioselectively occurred on the heteroarene rings to produce allylated dearomatization products or allylated heteroarenes with satisfactory yields.

Gold catalysis: Switching the pathway of the furan-yne cyclization

Changing tracks: By the use of alkynyl ethers as directing elements, the furan-yne cyclization enters a new reaction pathway. Instead of phenols, tetracycles containing two heteroatoms and two new stereocenters are formed (see scheme).

The reaction of N-magnesium derivatives of pyrroles with N- mesylchloromethylpyrroles: A synthesis of dipyrrylmethanes

Attachment of an alkyl- or arylsulfonyl group at the nitrogen atom of a pyrrole reduces the aromaticity and electron availability of the system. This is confirmed by the structure of an N-tosylated chloromethylpyrrole determined by X-ray crystallography. In agreement, N-mesylated chloromethylpyrroles are handleable materials which react smoothly with N- magnesium derivatives of pyrroles to provide a novel route for synthesis of dipyrrylmethanes. Several examples of this synthesis are described, including the construction of molecules carrying deuterium at the interpyrrolic methylene group.

Photochemical Transformations, 65. The 3? -> 3?-Route to 1H-Azepines/Benzene Imines

With several newly prepared substrates the influence of substituents upon the individual steps in the 3? -> 3?-route to 1H-azepines is more precisely defined: The C-unsubstituted 7-azanorbornadiene 2a, its 2,3-dichloro derivative 2b, the dimethyl 5,6-dichloro-2,3-dicarboxylate 2c, and the diesters 2d, e with dipolarophilic groups at C-1/N-7 are selectively isomerized by sensitized/direct photoexcitation into the azaquadricyclanes 29a-e, some of which are highly unstable.For the thermal conversion of the basic skeleton (N-Tos)29a the kinetic parameters have been determined (benzene): Ea = 28.0 +/- 0.2 kcal/mol, lg A = 15.7; ΔH* = 27.3 +/- 0.2 kcal/mol, ΔS* = 11.1 +/- 0.7 e.u.This barrier is lowered more efficiently by the chloro (29b, c) than by the methoxycarbonyl substituents (29f), with the former (latter) causing exclusive scission of the opposite (neighbouring) cyclopropane bonds.The intermediate azomethine ylides are captured with dipolarophilic reagents more or less efficiently depending on their substitution pattern.In the case of 29d(28d) the intramolecular addition of the unactivated yne component (37) at -30C is so fast, that azepine formation is almost totally suppressed (?2 + ?2 + Σ2>, 36?).The azepine/benzene imine equilibrium mixture 31c 32c (ca. 90:10) crystallizes as 31c (X-ray crystal structure analysis).