Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 18, Issue 6, Pages 1155-1164Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c9ob02501d
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Funding
- OPERA-grant of BITS Pilani
- DST-SERB [EMR/2016/005599]
- UGC-BSR
- BITS Pilani
- DST-FIST [SR/FST/CSI-270/2015]
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A simple and straightforward method for the synthesis of 4-iodo and 5-iodopyrrole-3-carboxaldehydes is developed from a common set of starting materials by tuning the reaction conditions. This sequential multicomponent protocol involves I-2-mediated regioselective C4-iodination and aromatization of intermediate dihydropyrrole, generated through proline-catalyzed direct Mannich reaction-cyclization sequence between succinaldehyde and imines, to access 4-iodopyrroles. While aerobic oxidative aromatization of dihydropyrrole to pyrrole followed by NIS-mediated regioselective iodination furnished 5-iodopyrroles in a two-pot fashion. A series of site-selective C4/C5-iodopyrroles have been synthesized in good to high yields (up to 78%) and DFT calculations of these compounds were also performed.
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