Thorpe condensation

Thorpe condensation of the dinitrile (1) was effected successfully with the reagent in t-butanol attempted cyclisation with sodium ethoxide or sodium in dioxane... 

Guareschi-Thorpe condensation. Synthesis of pyridine derivatives by condensation of cyanoa-cetic ester with acetoacetic ester in the presence of ammonia. In a second type of synthesis, a mixture of... 

This reaction is related to the Chichibabin Pyridine Synthesis Guareschi-Thorpe Condensation, and Hantzsch Dihydropyridine Synthesis. 

Early review F. Krohnke, Synthesis 1976, 1-24. Synthetic applications J. N. Chatteijea et al, Indian J. Chem. 15B, 430 (1977) G. R. Newkome etal, J. Org. Chem. 51, 850 (1986) P. Lhotak, A. Kurfiirst, Coll. Czech. Chem. Commun. 57,1937 (1992) T. R. Kelly et al, J. Org. Chem. 62, 2774 (1997). Cf. Chichibabin Pyridine Synthesis Guareschi-Thorpe Condensation Hantzsh (Dihydro)Pyridine Synthesis. 

A method which relied on the use of benzoyl isocyanate was developed for the synthesis of 5-fluoro-6-fluoromethylcytosine (971) (Scheme 207) [598], Thorpe condensation of fluoroacetonitrile generated unstable enamine 969, which reacted with benzoyl isocyanate in presence of pyridine to give urea derivative 970. Cyclization of 970 upon action of NaOEt led to the formation of 971. 

Barkin JL, Faust MD, Trenkle WC (2003) Cytosine analogues from substituted acetonitriles via Thorpe condensation. Org Lett 5 3333-3336... 

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