50691-32-2

Upstream product

• 33342-99-3 (+/-)-2-methyl-1-phenylpyrrolidine 
• 30186-39-1 N-phenylpyrrole-2-carbaldehyde 
• 123-76-2 levulinic acid 
• 62-53-3 aniline 
• 22414-24-0 2,5-dihydro-2,5-dimethoxy-2-methylfuran 
• 102516-18-7 methyl trans-2-methoxycyclopropyl ketone 
• 58518-63-1 2,5-dimethoxy-2-methyl-tetrahydro-furan 
• 534-22-5 2-methylfuran 
• 23132-35-6 levulinanilide 

Relevant academic research and scientific papers

Mild reduction with silanes and reductive amination of levulinic acid using a simple manganese catalyst

A manganese-based catalytic system using the commercially available complex [Mn(CO)5Br] was studied for the selective reduction of levulinic acid (LA) to 2-methyl-tetrahydrofuran (MTHF). We further studied the production of pyrrolidines via its reductive amination using silanes (phenylsilane and tetramethyldisiloxane). The results showed high efficiency and selectivity for this reaction leading to high yields using mild reaction conditions.

Method for preparing N-aryl pyrrole compound

The present invention relates to a method for preparing an N-aryl pyrrole compound. Furan containing different substituents, aromatic amine containing different substituents and a solid Lewis acid catalyst are mixed and placed in a closed reactor, and an N-aryl pyrrole compound with different substituents is prepared under certain catalytic conditions. The reaction temperature of the catalytic reaction condition is 140-210 DEG C. The solid Lewis acid catalyst is prepared by a sol-gel method, Hf is used as a core metal element, and a mesoporous molecular sieve SBA-15 is used as a carrier. According to the method, the catalyst is simple to prepare, low in cost, high in reaction activity, good in water resistance and structural stability and high in catalytic reaction yield; meanwhile, the Lewis acid type catalyst does not generate acid protons, the corrosion of the catalyst to equipment at high temperature is avoided, the post-reaction treatment is convenient, and the catalyst is renewable and environment-friendly.

Direct Synthesis of Pyrroles via Heterogeneous Catalytic Condensation of Anilines with Bioderived Furans

Given the wide applications of pyrroles in agriculture, pharmaceuticals, and supramolecular and materials chemistry, a mild and eco-friendly route to produce functionalized pyrroles from bioderived feedstocks is highly desirable. Described herein is a mild and convenient synthesis of pyrroles via direct condensation of an equimolar amount of structurally diverse anilines with biobased furans catalyzed by a simple and efficient solid acid H form zeolite Y catalyst. The protocol tolerates a large variety of functional groups and offers a general and versatile method for scale-up synthesis of a variety of N-substituted pyrrole compounds. Most importantly, the bioactive pyrrole-derived drug pyrvinium, which has lately been confirmed as highly effective in curing colon cancer, can be obtained by this method.

Reductive amination/cyclization of levulinic acid to pyrrolidones: Versus pyrrolidines by switching the catalyst from AlCl3 to RuCl3 under mild conditions

Herein the reductive amination/cyclization of levulinic acid using phenylsilane was presented to selectively produce pyrrolidones versus pyrrolidines under mild conditions by switching the catalyst from AlCl3 to RuCl3. Using AlCl3 as the catalyst, pyrrolidones were solely obtained at room temperature, while RuCl3 as the catalyst selectively afforded pyrrolidines in high yields at 45 °C.

PYRROLE ANTIFUNGAL AGENTS

The invention provides compounds of formula (I), and pharmaceutically and agriculturally acceptable salts thereof; wherein: R1, R2, R3, R4, R5, R6, A1, L1 and n are as defined herein. These compounds and their pharmaceutically acceptable salts are useful in prevention or treatment of a fungal disease. Compounds of formula (I), and agriculturally acceptable salts thereof, may also be used as agricultural fungicides.

Sulfur-Containing Heterocycles Derived by Reaction of ω-Keto Amides with Lawesson's Reagent

The reaction of ω-keto amides with Lawesson's reagent (LR: 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide) is described. Treatment of 3-keto amides (2-acylacetamides) 1 with LR gave the corresponding 3-keto thioamides 2, along with 1,2-dithiole-3-thiones 3. Treatment of 4-keto amides, 3-acyl propionamides 5, with LR yielded five-membered heterocycles, pyrroles 6 and/or 2-aminothiophenes 7. 5-Keto amides, 3-benzoyl butyramides 8, reacted with LR to give dihydrothiopyran-2-thione 9 as the sole product, but in low yield. 2-Acylbenzamides 10 also reacted with LR to afford 3-mercaptoisoindolin-2-ones 11 or dihydroisobenzothiophene-1-thiones 12.

SYNTHESIS OF PYRROLES FROM ALKYL trans-2-METHYLOXYCYCLOPROPYL KETONES

2-Alkylpyrroles were obtained by the reaction of alkyl trans-2-methoxycyclopropyl ketones with ammonium hydroxide.N-Substituted 2-alkylpyrroles were synthesized by the reaction of the indicated ketones with methylamine or aniline in acetic acid or methano