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  • Title: Access to indole- and pyrrole-fused diketopiperazines via tandem Ugi-4CR/intramolecular cyclization and its regioselective ring-opening by intermolecular transamidation.
    Author: Pandey S, Khan S, Singh A, Gauniyal HM, Kumar B, Chauhan PM.
    Journal: J Org Chem; 2012 Nov 16; 77(22):10211-27. PubMed ID: 23061967.
    Abstract:
    An efficient approach for the synthesis of indole- and pyrrole-fused diketopiperazines has been developed. This protocol involves the Ugi four-component reaction (U-4CR) followed by an intramolecular cyclization of the Ugi products at room temperature to afford the desired products in good to excellent yields. In addition, it is interesting to report the subsequent regioselective ring-opening of diketopiperazine unit occurring via an intermolecular transamidation reaction under mild condition, resulting in the formation of highly functionalized indole-2-carboxamides and pyrrole-2-carboxamides.
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