Tryptophan methyl ester 2 reacts with ethyl cyanoacetate to form acetomtrilocarbonyltryptophan methylester 3. The latter reacts with cyanomethylene reagents, hydrazines, cyanomethylenes and sulfur to form the corresponding a-pyrido-3-indolopropanoate derivatives 6a,b, pyrazolyltryptophan methyl ester derivatives 8a,b and thiophenotryptophan methyl ester derivatives 10a,b, respectively. Also compound 3 reacts with benzaldehyde to give the condensated product 12. The reactivity of the latter product towards chemical reagents was studied to form pyridine, pyrazole and isoxazole derivatives.