Guareschi-Thorpe Condensation

I. Guareschi, Mem. Reale Accad. Sci. Torino II, 46, 7, 11, 25 (1896); H. Baron, et al., J. Chem. Soc. 85, 1726 (1904).

Synthesis of pyridine derivatives by condensation of cyanoacetic ester with acetoacetic ester in the presence of ammonia. In a second type of synthesis a mixture of cyanoacetic ester and a ketone is treated with alcoholic ammonia:

C. Hollins, The Synthesis of Nitrogen Ring Compounds (New York, 1924) p 197; V. Migrdichian, The Chemistry of Organic Cyanogen Compounds (New York, 1947) p 322; H. S. Mosher, Heterocycl. Compd. 1, 466 (1950); R. W. Holder et al., J. Org. Chem. 47, 1445 (1982); D. J. Collins, A. M. James, Aust. J. Chem. 42, 215 (1989). Cf. Hantzsch (Dihydro)Pyridine Synthesis; Kröhnke Pyridine Synthesis.