92841-31-1

Basic information

• Product Name: 1-Indolizinecarboxylic acid, 3-cyano-2-phenyl-, methyl ester
• CAS NO: 92841-31-1
• Molecular Formula: C17H12N2O2
• Molecular Weight: 276.294
• Mol File: 92841-31-1.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 1-Indolizinecarboxylic acid, 3-cyano-2-phenyl-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Indolizinecarboxylic acid, 3-cyano-2-phenyl-, methyl ester(92841-31-1)
• EPA Substance Registry System: 1-Indolizinecarboxylic acid, 3-cyano-2-phenyl-, methyl ester(92841-31-1)

Safety Data

• Hazardous Substances Data: 92841-31-1(Hazardous Substances Data)

Upstream product

• 100-52-7 benzaldehyde 
• 27032-01-5 pyridinium 1-dicyanomethylide 
• 4891-38-7 phenylpropynoic acid methyl ester 

Relevant articles and documents

One-pot two-step synthesis of 1-(ethoxycarbonyl)indolizines via pyridinium ylides

Pyridinium salts Py+-CH2-EWG (EWG = CO2Et, CONEt2, CN, COMe, COPh) reacted with Michael acceptors Ar-CH=C(CO2Et)(Acc) (Acc = CO2Et, COMe, SO2Me, CONH2) at ambient temperature in the presence of base to give [3 + 2]-cycloadducts by stepwise [3 + 2]-cycloaddition of the intermediate pyridinium ylides. Treatment of the crude reaction mixtures with 1 equiv. of chloranil and atmospheric oxygen in the presence of sodium hydroxide gave 1-(ethoxycarbonyl)indolizines by dehydrogenation and elimination of the acceptor group (Acc). A good yield of indolizine was also obtained from Py +-CH2CN and iPr-CH=C(CO2Et)2, which indicates that this method is not restricted to aromatic Michael acceptors. Structurally related isoquinolinium salts react with Michael acceptors analogously to give pyrrolo[2,1-a]isoquinolines.