The Condensation of (Chlorocarbonyl)phenyl ketene with Bisnucleophiles

In this book, cycloaddition of chlorocarbonyl ketenes, effective 1,3-electrophiles in synthsis of heterocycles functionalized with oxo and hydroxyl groups, with 1,2 and 1,3-binucleophiles were described to prepare the five and six-membered heterocyclic compounds. Thus, (chlorocarbonyl)phenyl ketene (CCPK) was formed by distillation of phenyl malonyl chlorides by thermal dehydrohalogenation. Then to study the cycloaddition of this CCPK with enaminones as 1,3-binuleophiles, a series of substituted 5-acyl-2-pyridinone derivatives were prepared by this condensation and exhibited one tautomer. In countinuing, Schiff bases as 1,3-binucleophiles react with CCPK to produce the 2-(1H)-pyridinone derivatives and 1,3-oxazinium olate derivatives were also prepared by reaction of N-monosubstituted amide derivatives and CCPK when they are converted to other tautomeric forms. Finally, the pyrazole-trione derivatives were prepared by condensation of CCPK with N-unsubstituted pyrazolone derivatives as 1,2-binucleophile in mixture of two tautomers, but the 2-pyrone derivatives were produced by cycloaddition of CCPK with N-unsubstituted as 1,3-binucleophile in dry solvent and ambient temperature.

Autorentext

Dr. Mehdi Abaszadeh (born in May 1979) hold Ph.D. in organic chemistry from Shahid Bahonar University, Kerman, Iran in 2009. He is working as an Assistant Professor at Pharmaceutics Research Center, Kerman University of Medical Sciences. His Research interests cover different aspects of Heterocyclic Chemistry.