2199-44-2

Usage

Chemical Properties

Pale yellow to buff powder

Synthesis Reference(s)

Canadian Journal of Chemistry, 32, p. 812, 1954 DOI: 10.1139/v54-102Journal of the American Chemical Society, 77, p. 1546, 1955 DOI: 10.1021/ja01611a043Tetrahedron Letters, 36, p. 9469, 1995 DOI: 10.1016/0040-4039(95)02001-2

InChI:InChI=1/C9H8N4O2/c10-9-5-8(11-12-9)6-1-3-7(4-2-6)13(14)15/h1-5H,(H3,10,11,12)

Upstream product

• 5408-08-2 ethyl 4-iodo-3,5-dimethyl-1H-pyrrole-2-carboxylate 
• 64-19-7 acetic acid 
• 2386-26-7 ethyl 4-acetyl-3,5-dimethylpyrrole-2-carboxylate 
• 107-21-1 ethylene glycol 
• 90433-74-2 4-benzoyl-3,5-dimethyl-1H-pyrrole-2-carboxylic acid ethyl ester 
• 300-87-8 3,5-dimethyl-1,2-oxazole 
• 123844-20-2 ethyl 3-cyclopropylprop-2-ynoate 
• 131992-08-0 ethyl 4-<(acetoxyperchloryl)thallio>-3,5-dimethylpyrrole-2-carboxylate 

Downstream Products

• 2199-64-6 ethyl 3,5-dimethyl-4-formyl-1H-pyrrole-2-carboxylate 
• 75534-67-7 (5-ethoxycarbonyl-2,4-dimethyl-pyrrol-3-ylmethyl)-malonic acid diethyl ester 
• 101879-44-1 3,5-dimethyl-4-(3-phenyl-[1,2,4]thiadiazol-5-ylazo)-pyrrole-2-carboxylic acid ethyl ester 
• 6319-04-6 5-(5-ethoxycarbonyl-2,4-dimethyl-pyrrol-3-ylmethyl)-3-methyl-pyrrole-2,4-dicarboxylic acid diethyl ester 
• 40484-82-0 3,5-dimethyl-4-propionyl-1H-pyrrole-2-carboxylic acid ethyl ester 
• 2386-26-7 ethyl 4-acetyl-3,5-dimethylpyrrole-2-carboxylate 
• 95943-48-9 3,5,3',5'-tetramethyl-4,4'-phenylmethanediyl-bis-pyrrole-2-carboxylic acid diethyl ester 
• 90433-74-2 4-benzoyl-3,5-dimethyl-1H-pyrrole-2-carboxylic acid ethyl ester 
• 96067-63-9 3,5,3',5'-tetramethyl-4,4'-(4-dimethylamino-phenylmethanediyl)-bis-pyrrole-3-carboxylic acid diethyl ester 
• 858448-81-4 3,5-dimethyl-4-phenylsulfanyl-pyrrole-2-carboxylic acid ethyl ester 
• 40236-19-9 benzyl 3,5-dimethylpyrrole-2-carboxylate 
• 114721-92-5 4-(4-dimethylamino-cinnamylidene)-3,5-dimethyl-4H-pyrrole-2-carboxylic acid ethyl ester; perchlorate 
• 4513-93-3 3,5-dimethylpyrrole-2-carboxylic acid 
• 765923-45-3 3,5-dimethyl-pyrrole-2-carboxylic acid hydrazide 

Relevant academic research and scientific papers

Development of Gold-catalyzed [4+1] and [2+2+1]/[4+2] Annulations between Propiolate Derivatives and Isoxazoles

Two new gold-catalyzed annulations of isoxazoles with propiolates have been developed. Most isoxazoles follow an initial O attack on the alkyne to afford a [4+1] annulation product. This process results in a remarkable alkyne cleavage of initial propiolates. Unsubstituted isoxazoles proceed through an N attack step to yield formal [2+2+1]/[4+2] annulation products. These two annulation products arise initially from two seven-membered heterocyclic intermediates, which then lead to products.

THALLIUM AND MERCURY IN PYRROLE CHEMISTRY. USE OF C-THALLIATED AND C-MERCURIATED PYRROLE DERIVATIVES FOR SELECTIVE RING FUNCTIONALISATIONS via ipso-DETHALLIATION AND -DEMERCURIATION REACTIONS

The use of C-thalliated and C-mercuriated pyrroles to achieve selective introduction of various functional groups in a β position is described.High yields of hardly accessible pyrrole derivatives (such as nitropyrrole) can thus be obtained.

Deacylation of Pyrrole and other Aromatic Ketones

Ethyl 4-acetyl-3,5-dimethyl-1H-pyrrole-2-carboxylate (1a) reacts rapidly with ethylene glycol in refluxing benzene with p-toluenesulfonic acid or perchloric acid as a catalyst to give ethyl 3,5-dimethyl-1H-pyrrole-2-carboxylate (3) in high yield (96 percent).Various 2- and 3-acylpyrroles can be efficiently deacylated by using this procedure.Other ketones which undergo deacylation include phenyl(2-phenylindol-3-yl)methanone (19), 1-(5-methyl-1-phenylpyrazol-4-yl)ethanone (20), and 2,4-dimethoxybenzophenone.Certain pyrrole ketones where the acyl group is flanked by two ring methyl groups are also cleaved under acidic conditions by using ethanedithiol.