53391-61-0

Upstream product

• 96-54-8 N-Methylpyrrole 
• 108279-49-8 1-methylthiopyrrole 
• 57-06-7 N-allyl isothiocyanate 
• 74-88-4 methyl iodide 
• 109-97-7 pyrrole 
• 75-18-3 dimethylsulfide 
• 67-68-5 dimethyl sulfoxide 
• 624-92-0 Dimethyldisulphide 
• 856702-61-9 tert-butyl 2-(methylthio)-1H-pyrrole-1-carboxylate 
• 130408-93-4 2-Thiocyanato-1-triisopropylsilanyl-1H-pyrrole 
• 87549-06-2 1-(2-Benzenesulfonyl-ethyl)-2-methylsulfanyl-1H-pyrrole 
• 80964-97-2 dimethyl(2-pyrrolyl)sulfonium chloride 
• 33577-16-1 methyl methylsulfinylmethyl sulfide 
• 66786-05-8 2-thiocyanato-1H-pyrrole 

Downstream Products

• 87549-06-2 1-(2-Benzenesulfonyl-ethyl)-2-methylsulfanyl-1H-pyrrole 
• 156210-88-7 1-(5-(methylthio)-1H-pyrrol-2-yl)ethan-1-one 
• 75421-85-1 5-Methylthio-2-(phenylsulfinyl)pyrrole 
• 80965-00-0 2-(methylthio)-5-benzoylpyrrole 
• 82511-61-3 2-(methylsulfonyl)pyrrole 
• 80965-01-1 2-(methylthio)-5-(4-fluorobenzoyl)pyrrole 
• 90724-50-8 5-methylthio-1H-pyrrole-2-carboxaldehyde 
• 877305-37-8 1,9-bis(methylthio)-5-phenyldipyrromethane 
• 80965-06-6 [1-[3,3-(dimethoxycarbonyl)propyl]-2-methanesulfonyl-5-(4-fluorobenzoyl)]pyrrole 
• 80965-05-5 2-[2-(2-Benzoyl-5-methanesulfonyl-pyrrol-1-yl)-ethyl]-malonic acid dimethyl ester 
• 80965-04-4 [1-[2-(4,6-dioxo-2,2-dimethyl-1,3-dioxan-5-yl)ethyl]-2-(methanesulfonyl)-5-(benzoyl)]-pyrrole 

Relevant academic research and scientific papers

Methylthiolation for Electron-Rich Heteroarenes with DMSO-TsCl

DMSO-TsCl has been developed for direct methylthiolation of various electron-rich heteroarenes (more than 40 examples) with high regioselectivity in moderate to excellent yields (up to 96 %). Especially, pyrroles, furans, and thiophenes can be efficiently mono-methylthiolated. This practical method features scalable, metal-free, mild conditions and is compatible with air and moisture. Several applications of methylthiolated products were demonstrated for the first time. Based on controlled experimental results, a plausible mechanism was proposed with two key intermediates involved in the mechanism being detected by HRMS.

Access to indoles via Diels-Alder reactions of 5-methylthio-2-vinylpyrroles with maleimides

Diels-Alder reactions of 5-methylthio-2-vinyl-1H-pyrroles with maleimides followed by isomerization gave tetrahydroindoles in moderate to good yield. Aromatization using activated MnO2 in refluxing toluene gave the corresponding 2-methylthioindoles in good yields, and demethylthioation using Raney nickel gave the 2-H indoles in excellent yields. The protection of the adducts produced aromatization in improved yield, demonstrating the effectiveness of the methylthio group as a protecting group for pyrroles; however, 5-methylthio-2-vinylpyrrole was shown to perform with slightly less efficiency than 2-vinylpyrrole in Diels-Alder reactions, indicating the protective group was more deactivating than desired. This route toward indoles offers high convergency and conveniently available starting materials that are easily purified. Bis-methylthioated vinylpyrroles were shown to have potential as highly activated Diels-Alder dienes.

Structural reorganization of allyl isothiocyanate into pyrrole ring under superbase: A straightforward access to NH-2-(Alkylsulfanyl)-1H-pyrroles and N-Alkyl-2-(alkylsulfanyl)-1H-pyrroles

A novel and facile synthetic route to NH-2-(alkylsulfanyl)-1H-pyrroles and N-alkyl-2-(alkylsulfanyl)-1H-pyrroles is reported. This was achieved by deprotonation of allyl isothiocyanate with the superbasic pair lithium diisopropylamide and potassium tert-butoxide (1:1 molar mixture), followed by intramolecular ring closure, deprotonation of cyclic anion with a second equivalent of the superbase, and final sequential N-protolysis/S-alkylation or N,S-dialkylation of the formed N,S-centered pyrrol-2-ylsulfide dianion. Georg Thieme Verlag Stuttgart · New York.

Geometric synthesis of porphyrin rods

A method of making a compound of Formula I′ comprises reacting a compound of the formula DLCHO, with a compound of the formula to produce the compound of Formula I′. Methods of using the compounds are also described, particularly as intermediates for the synthesis of porphyrin rods, which porphyrin rods are in turn useful for (among other things) the production of molecular memory devices.

Accelerated arene ligand exchange in the (arene)Cr(CO)2L series

Arene ligand exchange in the (η6-arene)Cr(CO)2L series can be accelerated if the ligand L is an electronically unsymmetrical bidentate ligand. The system evaluated here employs derivatives of tris(pyrrolyl)-phosphine as L. A series of 2-L′-substituted pyrroles was prepared, where the substituents include: L′= -SMe, -CH2SMe, -SPh, -CH2SPh, -SCF3, -S-tBu, -CO2Me, -CONMe2, -2-pyridinyl, and -PPh2. Reaction with CIP(pyrrolyl)2 gave a new series of phosphines, (2-L′-pyrrolyl) (pyrrolyl)2P. Each of these phosphines was converted to (arene)Cr(CO)2[P(2-L′-pyrrolyl)(pyrrolyl)2P) complexes. The substituents L′ are proposed to provide temporary coordination to the Cr and to lower the barrier to arene exchange. The series was evaluated where the arene in the complex (departing) is benzene, fluorobenzene, toluene, o-oxylene, m-xylene, or p-xylene and the incoming arene is C6D6, chlorobenzene-d5, anisole-d 8, fluorobenzene-d5, toluene-d8, o-oxylene-d10, m-xylene-d10, p-xylene-d10, or mesitylene-d12. Most of the new complexes showed a significant increase in the rate of arene exchange due to the side chain unit L′. The strongest effects were seen with the examples where X = -CO2Me, -CONMe2, and -(2-pyridinyl), allowing exchange with a half lifetime as low as 8 h/22 °C.

MODULATORS OF CELLULAR ADHESION

The present invention provides compounds having formula (I): and pharmaceutically acceptable derivatives thereof, wherein R1-R4, n, p, A, B, D, E, L and AR1 are as described generally and in classes and subclasses herein, and additionally provides pharmaceutical compositions thereof, and methods for the use thereof for the treatment of disorders mediated by the CD11/CD18 family of cellular adhesion molecules (e.g., LFA-1).

A simple preparative method for 2-alkylthiopyrroles

A number of 2-alkylthiopyrroles have been obtained in fair yields by metallation of allyl isothiocyanate with a mixture of lithium diisopropylamide and potassium tert-butoxide, followed by successive addition of water and alkyl halide.

N-(Triisopropylsilyl)pyrrole. A Progenitor "Par Excellence" of 3-Substituted Pyrroles

A very effective strategy has been devised for the synthesis of 3-substituted pyrroles based on the use of the triisopropylsilyl (TIPS) moiety as a sterically demanding nitrogen substituent to obstruct the attack of electrophilic reagents at the α positions. 1-(Triisopropylsilyl)pyrrole (1) undergoes highly preferential kinetic electrophilic substitution at the β position with a variety of electrophiles (Br+, I+, NO2+, RCO+, etc.) and fluoride ion induced desilylation of the products provides the corresponding 3-substituted pyrroles in good overall yields.Competitive trifluoroacetylation experiments demonstrate that substitution of TIPS-pyrrole at the α positions is decelerated by a factor of >104, vs pyrrole at the same sites, without affecting reactivity at the β positions. 1-(Triisopropylsilyl)-3-bromopyrrole (2) is readily converted into the 3-lithio compound 44 by bromine-lithium interchange with alkyllithium reagents.This previously unavailable, formal equivalent of 3-lithiopyrrole is itself an excellent source of a wide range of β-substituted pyrroles, many of which would not be directly preparable from 1.TIPS-pyrrole can be 3,4-dihalogenated and these compounds undergo sequential halogen-metal interchange trapping reactions.This process is exemplified by an efficient, three-step synthesis of the antibiotic verrucarin E (63) from the dibromo compound (5).