52179-70-1

Usage

Synthesis Reference(s)

Tetrahedron, 51, p. 13271, 1995 DOI: 10.1016/0040-4020(95)00851-X

Upstream product

• 107-13-1 acrylonitrile 
• 202286-41-7 N-(benzotriazol-1-ylmethyl)-α-(methylthio)phenylimine 
• 614-16-4 Benzoylacetonitrile 
• 93-58-3 benzoic acid methyl ester 
• 117067-55-7 N-(benzotriazol-1-ylmethyl)thiobenzoamide 
• 74895-37-7 2-Cyan-4,4-diethoxybuttersaeurenitril 
• 98-80-6 phenylboronic acid 

Relevant academic research and scientific papers

IBX-Promoted Oxidative Cyclization of N-Hydroxyalkyl Enamines: A Metal-Free Approach toward 2,3-Disubstituted Pyrroles and Pyridines

An iodoxybenzoic acid-mediated selected oxidative cyclization of N-hydroxyalkyl enamines was developed. Through this strategy, a variety of 2,3-disubstituted pyrroles and pyridines were produced in good selectivity involving oxidation of alcohol, followed by condensation of aldehyde and α-C of enamines. Furthermore, this metal-free method has several advantages, including the use of environmentally friendly reagents, broad substrate scope, mild reaction conditions, and high efficiency.

2-aryl-3-ester-group polysubstituted pyrrole compound and synthesis and refining method thereof

The invention belongs to the field of chemical synthesis, and relates to a series of 2-aryl-3-ester-group polysubstituted pyrrole compounds and a synthesis and refining method thereof. A general formula of the compounds is shown as a formula (I), wherein

One-Pot Synthesis of 3-Substituted 2-Arylpyrrole in Aqueous Media via Addition-Annulation of Arylboronic Acid and Substituted Aliphatic Nitriles

Pd(II)-catalyzed C-C coupling reactions between substituted aliphatic nitriles and arylboronic acids followed by in situ cyclodehydration have been employed for the first time to synthesize a wide variety of 3-substituted 2-aryl-1H-pyrroles in aqueous acetic acid. This one-pot synthesis is green, and it conforms to atom economy. The structures of two representative pyrroles, 3k and 5f, were confirmed by X-ray crystallographic analysis.

A Route to 2-Substituted 3-Cyanopyrroles: Synthesis of Danaidal and Suffrutine A

The title compounds were prepared in a two-step sequence from 4,4-dimethoxybutyronitrile and the respective esters by Claisen condensation and subsequent Paal-Knorr pyrrole synthesis. The sequence could be performed as a one-pot procedure delivering the pyrroles in yields of 47-72% over two steps (13 examples). Intramolecular variants of the method were applied to the total synthesis of danaidal and suffrutine A from the respective trityl-protected ω-amino alkanoates.

SUBSTITUTED PYRROLES ACTIVE AS KINASES INHIBITORS

The present invention relates to substituted pyrrole compounds which modulate the activity of protein kinases and are therefore useful in treating diseases caused by dysregulated protein kinase activity, in particular Jak family kinases. The present invention also provides methods for preparing these compounds, pharmaceutical compositions comprising these compounds, and methods of treating diseases utilizing such compounds or the pharmaceutical compositions containing them.

Novel and convenient routes to substituted pyrroles and imidazoles

S-Methyl N-(benzotriazol-1-ylmethyl)thioimidate 6 is obtained by lithiation of the corresponding N-(benzotriazol-1-ylmethyl)thioamide 5 and subsequent reaction with methyl iodide. Derivative 6 undergoes [2+3] cycloaddition reactions with α,β-unsaturated -esters, -ketones and -nitriles, and vinylpyridines which are followed by elimination of benzotriazole and the thioalkoxy group, to give 2,3,4-trisubstituted pyrroles. Lithiation of 6 followed by reactions with imines gives cyclized 4,5-dihydroimidazoles 14 which upon further treatment with ZnBr2 or direct refluxing in toluene yield the 1,2,5-trisubstituted imidazoles 15 in good yields.