Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 23, Pages 17213-17225Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c02295
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Funding
- BITS Pilani
- DST-SERB
- SERB, New Delhi [CRG/2020/003424]
- DST-FIST, New Delhi [SR/FST/CSI-270/2015]
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A direct aza-Diels-Alder reaction between 2-aryl-3H-indolin-3-ones and cyclic-enones has been developed to access chiral indolin-3-one fused polycyclic bridged compounds. The method involves proline-catalyzed Barbas-dienamine intermediate formation from various cyclic-enones and has shown exciting photophysical activities. The synthesized compounds selectively sense Pd2+ and Fe3+ ions through the fluorescence quenching switch-off mode.
A direct aza-Diels-Alder reaction between 2-aryl-3H-indolin-3-ones and cyclic-enones has been developed to access chiral indolin-3-one fused polycyclic bridged compounds. This method proceeds via proline-catalyzed Barbas-dienamine intermediate formation from various cyclic-enones such as 2-cyclopenten-l-one, 2-cyclohexene-l-one, and 2-cycloheptene-l-one, followed by a reaction with 2-aryl-3H-indol-3-ones. Several indolin-3-ones fusing [2.2.2], [2.2.1], and [3.2.1] skeletons decorated with a tertiary carbon chiral center have been prepared. Computational studies (DFT) supported the observed stereoselectivity in the method. The synthesized compounds have shown exciting photophysical activities and selective sensing of Pd2+ and Fe3+ ions through the fluorescence quenching switch-off mode.
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