90908-89-7

Usage

Chemical Properties

Off-White Solid

Uses

2-Cyanoacetylpyrrole (cas# 90908-89-7) is a compound useful in organic synthesis.

Upstream product

• 109-97-7 pyrrole 
• 372-09-8 cyanoacetic acid 
• 109-77-3 malononitrile 

Downstream Products

• 1446135-44-9 2-(1-(4-nitrobenzyl)-1H-tetrazol-5-yl)-1-(1H-pyrrol-2-yl)ethanone O-tosyl oxime 
• 1446135-43-8 5-(3-(1H-pyrrol-2-yl)-2H-azirin-2-yl)-2-(4-nitrobenzyl)-2H-tetrazole 
• 1446135-34-7 2-(2-(4-nitrobenzyl)-2H-tetrazol-5-yl)-1-(1H-pyrrol-2-yl)ethanone oxime 

Relevant academic research and scientific papers

Microwave-Assisted Three-Component Domino Synthesis of Polysubstituted 4H-Pyran Derivatives and Their Anticancer Activity

Abstract: An efficient microwave-assisted one-pot procedure has been proposed for thesynthesis of new 4-aryl-6-(methylamino)-5-nitro-2-(1H-pyrrol-2-yl)-4H-pyran-3-carbonitriles by condensation of 3-oxo-3-(1H-pyrrol-2-yl)propanenitrile with (E)-N-methyl-1-(methylsulfanyl)-2-nitroethenamine and substitutedbenzaldehydes in the presence of a catalytic amount of piperidine using ethanolas a solvent. The transformation occurs via successive Knoevenagel condensation,Michael addition, and intramolecular cyclization. The proposed procedure isadvantageous due to its one-pot mode, short reaction time, simple purificationby recrystallization, and excellent yields. The product structure was confirmedusing various spectroscopic techniques, including IR,1H and 13C NMR, LC/MS,elemental analysis, and single crystal X-ray diffraction study. The synthesizedcompounds were evaluated for their anticancer activity against 60 differenthuman cancer cell lines in nine cancer panels, and two compounds were found tobe potent against different cell lines.

Simple Synthesis of 3-Oxopropanenitriles via Electrophilic Cyanoacetylation of Heterocycles with Mixed Anhydrides

A simple and efficient method for the synthesis of 3-oxopropanenitriles from variously substituted heterocyclic compounds via direct electrophilic cyanoacetylation is described. A series of heterocyclic 3-oxopropanenitriles (2a, 2b, 2c, 2d, 2e, 2f, 2g, 2h, 2i, 2j, 2k) have been synthesized using mixed anhydride (acetic or trifluoroacetic anhydride:cyanoacetic acid) in the presence of Mg(ClO4)2·2H2O as catalyst. This method can be extended also for the cyanoacetylation of electron poor aromatic compounds.

Discovery of acrylonitrile-based small molecules active against Haemonchus contortus

We report the discovery of a series of acrylonitrile-containing molecules and α-amino amides which cause 99-100% lethality in H. contortus. Of the 22 acrylonitrile analogues investigated, the most active were 2-cyano-3-[1-(3-dimethylaminopropyl)-2-methyl-

Focused library development of 2-phenylacrylamides as broad spectrum cytotoxic agents

With our lead compound (E)-3-(4-chlorophenyl)-2-(1H-pyrrole-2-carbonyl) acrylonitrile (1) inducing 50% growth inhibition of 11 cancer cell lines at 27-61 μM, potency enhancements were rapidly established through the synthesis of a series of focused compou

The neber approach to 2-(tetrazol-5-yl)-2 H -azirines

The synthesis of 2-(tetrazol-5-yl)-2H-azirines is reported for the first time. Using the Neber approach, β-ketoxime-1H-tetrazoles were converted into the target 2H-azirines bearing phenyl, furan-2-yl, thiophen-2-yl, or pyrrol-2-yl substituents at C-3. It was demonstrated that the alkaloid-mediated Neber reaction allows the asymmetric synthesis of 2-(tetrazol-5-yl)-2H-azirines.

New approach to 4- and 5-aminopyrazole derivatives

3-Oxo-3-(pyrrol-2-yl)-propanenitrile 1 coupled with aromatic diazonium salts to yield the corresponding 2-arylhydrazones 2a-c. The latter products reacted with chloroacetonitrile and ethyl chloroacetate to yield 4-aminopyrazole derivatives 5a-f. Reaction

Cyanoacetylation of indoles, pyrroles and aromatic amines with the combination cyanoacetic acid and acetic anhydride

Cyanoacetic acid was activated with acetic anhydride and when heated this reagent reacted with a variety of both activated and deactivated pyrroles, indoles and aniline derivatives.

Certain β-oxo-α-carbamoylpyrrolepropionitriles

1-Unsubstituted β-oxo-α-(phenylcarbamoyl)-β-pyrrolylpropionitriles, e.g. those of the formula STR1 wherein R1 and R2 =H or alkyl, and R3 and R4 =H, alkyl, alkoxy, OH, halogen or CF3, are analgesic, and antiarthritic agents. Their synthesis, pharmaceutical compositions thereof, and methods of treatment utilizing such compounds are included.