Novel Pyridine-Catalyzed Reactionof Dimethyl Acetylenedicarboxylate with Aldehydes and N-Tosylimines: Efficient Synthesis of2-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

doi:10.1055/s-2003-41000

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Novel Pyridine-Catalyzed Reactionof Dimethyl Acetylenedicarboxylate with Aldehydes and N-Tosylimines: Efficient Synthesis of2-Benzoylfumarates and 1-Azadienes

Vijay Nair*^a, A. R. Sreekanth^a, N. Abhilash^a, A. T. Biju^a, B. Rema Devi^a, Rajeev. S. Menon^a, Nigam P. Rath^b, R. Srinivas^c
^a Organic Chemistry Division, Regional Research Laboratory (CSIR), Trivandrum695 019, India
Fax: +91(472)2491712; e-Mail: vijaynair_2001@yahoo.com;
^b Department of Chemistry, Universityof Missouri-St. Louis, Missouri-63121-4499, USA
^c National Center for Mass Spectrometry, Indian Institute of Chemical Technology (CSIR), Hyderabad 500 007, India

Abstract

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Abstract

A novel reaction of 1,4-dipolar intermediate 3,generated from pyridine and dimethyl acetylenedicarboxylate, witharomatic aldehydes, resulted in the facile synthesis of 2-benzoylfumaratesvia the elimination of pyridine, whereas with N-tosyliminesas dipolarophiles the reaction afforded highly substituted 1-azadienes.The reaction of pyridine and dimethyl acetylenedicarboxylate withN-substituted isatins, resulted in a novel three component condensation,affording spiropyrido[2,1-b][1,3]oxazinoderivatives in high yields via 1,4-dipolar cycloaddition.

Key words

aldehyde - pyridine - nucleophilic additions - dimethyl acetylenedicarboxylate - 1,4-dipolar cycloadditions

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References

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