589-33-3

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 45, p. 3172, 1980 DOI: 10.1021/jo01304a006

InChI:InChI=1/C8H13N/c1-2-3-6-9-7-4-5-8-9/h4-5,7-8H,2-3,6H2,1H3

Upstream product

• 696-59-3 cis,trans-2,5-dimethoxytetrahydrofuran 
• 109-73-9 N-butylamine 
• 109-97-7 pyrrole 
• 87-73-0 D-glucaric acid 
• 526-99-8 meso-galactaric acid 
• 69309-33-7 1,4-bis-(dimethylamino)-1,3-butadiene 
• 109-65-9 1-bromo-butane 
• 542-69-8 1-iodo-butane 
• 109-69-3 n-Butyl chloride 
• 7697-45-2 sodium pyrrolide 
• 16199-06-7 potassium pyrrolide 
• 778-28-9 butyl para-toluenesulfonate 
• 98019-88-6 3,4-Dibrom-butyraldehyd 
• 145939-75-9 1-formyl-2-chlorocyclopropane 

Downstream Products

• 2672-57-3 benzene-1,2,3-tricarboxylic acid trimethyl ester 
• 74986-26-8 trimethyl 1-butylpyrrole-2,3,4-tricarboxylate 
• 74986-08-6 dimethyl (E)-1-butyl-2-pyrrolyl-2-butenedioate 
• 74985-96-9 dimethyl (Z)-1-butyl-2-pyrrolyl-2-butenedioate 
• 4789-08-6 1-Butyl 2-Piperidinone 
• 1257847-62-3 1-butyl-2-(dicyclohexylphosphino)-1H-pyrrole 
• 223437-11-4 1-butyl-methylpyrrolidinium bis(trifluoromethylsulfonyl)amide 
• 767-10-2 1-butylpyrrolidine 

Relevant academic research and scientific papers

Photolysis of pyridazine N-oxides; formation of cyclopropenyl ketones

Irradiation of pyridazine N-oxides with primary amines in dichloromethane gives N-substituted pyrroles, suggesting that cyclopropenyl ketones are intermediates.

Sterically controlled C-H alkenylation of pyrroles and thiophenes

Pd-catalyzed C-H alkenylations targeting the least hindered position of N-alkyl pyrroles and 3-substituted thiophenes, as opposed to electronically controlled approaches, are developed. The steric demand and stable bidentate binding mode of the pyrazolonaphthyridine ligand are key to the success of these sterically controlled alkenylations using oxygen as an oxidant.

Nickel-Catalyzed Synthesis of N-Substituted Pyrroles Using Diols with Aryl- and Alkylamines

Herein, nickel-catalyzed sustainable strategy for the synthesis of N-substituted pyrroles using butene-1,4-diols and butyne-1,4-diols with a series of aryl-, alkyl-, and heteroarylamines is reported. The catalytic protocol is tolerant of free alcohol, halide, alkyl, alkoxy, oxygen heterocycles, activated benzyl, and the pyridine moiety and resulted in up to 90% yield. Initial mechanistic studies involving defined nickel catalyst, determination of rate, and order of reaction including deuterium-labeling experiments were performed for pyrrole synthesis.

A new facile approach to N-alkylpyrroles from direct redox reaction of 4-hydroxy-l-proline with aldehydes

An unprecedented acetic acid-catalyzed efficient access to N-alkylpyrroles from reaction of 4-hydroxy-l-proline with a variety of aldehydes has been achieved in good to excellent yields under mild reaction conditions.

Direct amination of secondary alcohols using ammonia

Hydrogen shuttle: For the first time secondary alcohols and ammonia can be directly converted into primary amines with a selectivity of up to 99% by using a simple ruthenium/phosphine catalyst (see scheme; R1, R2= alkyl, aryl, alkenyl; M=[Ru3(CO)12]; and L=phosphine ligand).

Reversion of Paal-Knorr synthesis: A new strategy for ring-opening and N-substituent change in 1H-pyrroles

1H-Pyrroles were converted into 1,4-dicarbonyl compounds, and then into 1H-pyrroles with a different N-substituent by heating at 110 °C under nitrogen in 0.3 M sodium citrate buffer, pH 3, and in the presence of alkyl or aryl amines. The new pyrroles were obtained in low to very high yields depending upon the pH, the reaction time, the initial pyrrole and amine involved, and the proportion between both reagents. Georg Thieme Verlag Stuttgart.

Organic reactions in ionic liquids: A simple and highly regioselective N-substitution of pyrrole

In ionic liquids [Bmim][PF6] or [Bmim][BF4], pyrrole replaced the halogen atom of an alkyl halide to give the corresponding N-substituted pyrrole in excellent yield. Benzenesulfonyl chloride, p-methylbenzenesulfonyl chloride and benzoyl chloride reacted similarly with pyrroles to afford the N-substituted pyrroles in quantitative yield. Michael addition reaction of pyrrole with electrophilic olefins was completed in a highly regioselective manner to afford the N-alkylpyrroles.

Synthesis and structure-activity relationships of aroylpyrrole alkylamide bradykinin (B2) antagonists

The synthesis and structure-activity relationships of a novel series of aroylpyrrole alkylamides as potent selective bradykinin B2 receptor antagonists are described. Several members of this series display nanomolar affinity at the B2 receptor and show activity in an animal model of antinociception.

Radical cycloaddition by nickel(II) complex-catalyzed electroreduction. A method for preparation of pyrrolopyridine and pyrrolopyrrole derivatives

Cycloalkano[a]pyrroles were obtained by reductive radical cycloaddition of 1-(2-iodoethyl)pyrrole and activated olefins or by cyclization of 1-(ω- iodoalkyl)pyrroles, through electroreduction of the iodides using nickel(II) complex as an electron-transfer catalyst.

Synthesis and properties of low-bandgap zwitterionic and planar conjugated pyrrole-derived polymeric sensors. Reversible optical absorption maxima from the UV on the near-IR

Described are the polymerizations of three new dibrominated carbonyl-stabilized ylide monomers using copper-bronze in DME to afford polymers that are soluble in common solvents and have unique optical and electronic properties. The first monomer is a zwitterionic N-butylpyrrolinium oxide derivative which, upon polymerization, gives a polymer that has a strong optical absorbance at 520 nm in CCl4. An interunit ionic interaction is proposed to explain this large red-shifted band. Bronsted bases and Lewis bases induce a reversible structural change in the polymer to give bathochromic shifts from the visible to the near-IR spectral region. Upon mild reduction of the zwitterionic polymer with Pd/C and H2 (1 atm), some of the extended conjugation is lost, but a polymer forms that has an enormous optical absorption maximum range from the near-LV (290 nm) to the near-IR (886 nm) depending on the solvent or hydroxide concentration. A sample of the reduced polymer can be dispersed in platicized poly(vinyl chloride). The flexible polymer composite reversibly changes from dark blue-brown in aqueous sodium hydroxide to bright yellow-orange in aqueous HCl. The second monomer, a zwitterionic N-dodecylpyrrolinium oxide derivative, was also synthesized in three steps from pyrrole and, upon polymerization, gives rise to a polymer which also responds reversibly toward Bronsted and Lewis bases. This polymer can be solution cast into flexible free-standing films. The third monomer is a zwitterionic N-[oligo(ethylene glycol) monomethyl ether]pyrrolinium oxide derivative which, upon polymerization, affords a polymer that not only responds reversibly toward Bronsted and Lewis bases but also is water soluble and optically sensitive toward the addition of specific salts. The presence of the oligoethylene substituents is critical for the dramatic ionochromic response. Additionally, Pd-catalyzed cross-coupling methodology can be used for the incorporation of the N-butylpyrrolinium oxide monomer unit into an AB-type oligomeric system where the B component is a 1,4-phenylene moiety.