Unexpected one-pot synthesis of new polycyclic coumarin[4,3-c]pyridine derivatives via a tandem hetero-Diels-Alder and 1,3-dipolar cycloaddition reaction |
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Authors: | Daman R Gautam Konstantina C Fylaktakidou Demetrios N Nicolaides |
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Institution: | a Laboratory of Organic Chemistry, Aristotle University of Thessaloniki, 54124 Thessaloniki, Greece b Molecular Biology and Genetics Department, Democritus University of Thrace, 68100 Alexandroupolis, Greece |
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Abstract: | O-Methyl-4-coumarincarbaldehyde oxime reacted as an azadiene with electron-deficient and electron-rich dienophiles to give, via one-step hetero-Diels-Alder cycloaddition reactions, the corresponding 5H-coumarin4,3-c]pyridin-5-ones. When excess of the dienophile was used, fused azatetracyclo derivatives were also formed via a tandem Diels-Alder and 1,3-dipolar cycloaddition reaction of the dienophile to an azomethine ylide formed by the intermediate 2,3-dihydro-5H-coumarin4,3-c]pyridine-5-one. The regio- and stereoselectivities of the new compounds correspond well with spectroscopic (2D NMR) and theoretical data. A possible mechanistic scheme is provided. |
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Keywords: | 1-Azadienes Azomethine ylide Coumarins 1 3-Dipolar cycloadditions Hetero-Diels-Alder reactions Pyridocoumarins |
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