Synthesis of pyrrolo[3,4-b]pyrroles and perhydrothiazolo[3′,4′-2,3]pyrrolo[4,5-c]pyrroles |
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Authors: | Mahalingam Poornachandran |
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Affiliation: | Department of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600025, India |
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Abstract: | The 1,3-dipolar cycloaddition reactions of various N-tethered alkenyl aldehydes with some cyclic and acyclic amino acids have been studied. Some key sulfonamides having strategically positioned aldehyde and olefinic tether have been synthesized and effectively subjected to intramolecular azomethine ylide cycloaddition reaction resulting in a series of pyrrolo[3,4-b]pyrrole and its N-1-C-2 derivatives, and a series of novel heterotricyclic compounds, perhydrothiazolo[3′,4′-2,3]pyrrolo[4,5-c]pyrroles, in good yields. The intramolecular cycloaddition reaction was found to be highly stereoselective to form only cis-fused cycloadducts in all cases. |
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Keywords: | Pyrrolidine Pyrrolo[3,4-b]pyrrole Cycloaddition Heterotricycle Perhydrothiazolo[3&prime ,4&prime -2,3]pyrrolo[4,5-c]pyrrole Stereoselective Azomethine ylide Alkenyl aldehyde |
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