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Novel Pyridine-Catalyzed Reaction of Dimethyl Acetylenedicarboxylate with Aldehydes and N-Tosylimines: Efficient Synthesis of 2-Benzoylfumarates and 1-Azadienes

Vijay Nair*, A. R. Sreekanth, N. Abhilash, A. T. Biju, B. Rema Devi, Rajeev. S. Menon, Nigam P. Rath, R. Srinivas

*Organic Chemistry Division, Regional Research Laboratory (CSIR), Trivandrum 695 019, India, Email:

V. Nair, A. R. Sreekanth, N. Abhilash, A. T. Biju, B. R. Devi, R. S. Menon, N. P. Rath, R. Srinivas, Synthesis, 2003, 1895-1902.

DOI: 10.1055/s-2003-41000


A 1,4-dipolar intermediate generated from pyridine and dimethyl acetylenedicarboxylate reacted with aldehydes to give 2-benzoylfumarates via the elimination of pyridine, whereas with N-tosylimines as dipolarophiles the reaction afforded highly substituted 1-azadienes.

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A Novel Synthesis of 2-Aminopyrroles Using a Three-Component Reaction

V. Nair, A. U. Vinod, C. Rajesh, J. Org. Chem., 2001, 66, 4427-4429.

Key Words

enones, imines, pyridine, nucleophilic additions, dimethyl acetylenedicarboxylate, 1,4-dipolar cycloadditions, organocatalysis

ID: J66-Y2003-1930