42455-45-8

Upstream product

• 21835-71-2 4-(4-dimethylamino-phenyl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl ester 
• 53338-49-1 4-(4-dimethylamino-phenyl)-2,6-dimethyl-pyridine-3,5-dicarboxylic acid diethyl ester 
• 52287-57-7 2-nitro-1-(4'-dimethylaminophenyl)-1-propene 
• 141-97-9 ethyl acetoacetate 

Relevant academic research and scientific papers

Ring-contraction of hantzsch esters and their derivatives to pyrrolesviaelectrochemical extrusion of ethyl acetate out of aromatic rings

Electrochemical ring-contraction of HEs and theirs pyridine derivatives is developed to obtain polysubstituted pyrroles. This process provides an orthogonal utilization of Hantzsch esters for the well-documented application as side chain or hydrogen donors. The formal transformation shows an extrusion of ethyl acetate out of the pyridine ring in a single step. In addition to the novel transformation, we also discovered the Lewis acid's intermolecular control of regioselectivity during an intramolecular electrochemical process. The reaction provides a number of polysubstituted pyrroles that have never been accessed, including pharmaceutical intermediates and photoswitches. An unusual 4-electron continuous reduction drives the unprecedented anionic dearomatization/ring-contraction/rearomatization pathway.

Heterocycles from α-Nitroolefins, VIII. - 2-Methyl-3-pyrrolecarboxylates from α-Nitroolefins and Acetoacetates

3-Pyrrolecarboxylates 4 can be prepared from α-nitroolefins 1 and acetoacetates 2 by two methods: (a) 1 and 2 react to give 4,5-dihydro-5-methyleneamino-3-furancarboxylates 3 which are hydrolyzed, (b) the nitronic acids 8, adducts of 1 and 2, yield with different reduction agents the heterocycles 4.