A synthetic strategy that affords 1H-pyrrol-3(2H)-ones (2) and 3’,8a-dihydrocyclopenta[hi]indolizin-8a-ols (3) using cycloaddition of indolizinones with DMAD as the key step is discussed. These products arise either through [4+2] or [8+2] mode of cycloaddition of DMAD with the indolizinone moiety.1 3’,8a-dihydrocyclopenta[hi]indolizin-8a-ols on treatment with HBF4.Et2O affords a new class of cyclazine analogs with periphery reminiscent of aza[10]annulene framework, tethered internally by sp3 carbon.2 In-depth structure analysis based on NMR and X-ray diffraction data gave a deeper insight into the effect of electron delocalization on their structure and properties. Characteristic change in chemical shift positions suggested aromatic ring current in these systems. Attractive emission properties in solid- and solution states involving charge transfer is another highlight.

Ring Current Effects and Substituent Driven Emissive Properties in a Higher Homologue of Pyridine

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27th CRSI National Symposium in Chemistry

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