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| PAPER | Synthesis 2003: 1895-1902
DOI: 10.1055/s-2003-41000 |
© Georg ThiemeVerlag Stuttgart · New York
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Novel Pyridine-Catalyzed Reactionof Dimethyl Acetylenedicarboxylate with Aldehydes and N-Tosylimines: Efficient Synthesis of2-Benzoylfumarates and 1-Azadienes
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| Vijay Nair*a, A. R. Sreekantha, N. Abhilasha, A. T. Bijua, B. Rema Devia, Rajeev. S. Menona, Nigam P. Rathb, R. Srinivasc |
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
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Received
4 November 2002 |
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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