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Interesting reactivity of diketones with pyrrole under acidic condition

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Abstract

The acid catalysed condensation of diketones with pyrrole did not result in the formation of expected divergent bisdipyrromethane always; instead the product depends on the chain length of the diketones, in particular the distance between the two carbonyl functional groups. When the two carbonyl groups are linked via one or two methylene groups, unusual ring annulation occurs resulting in the formation of various bridged bipyrroles. However, on further increase in the length of the spacer, between the two carbonyl groups, synthesis of the expected bisdipyrromethanes could be achieved.

The synthesis of divergent bisdipyrromethanes with alkyl chain as spacer is achieved using the simple acid catalysed condensation of terminal alkanedione (n≥3) and pyrrole. With shorter bridged alkyl chain, ring annulated products are obtained.

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Authors and Affiliations

  1. School of Chemistry, University of Hyderabad, Gachibowli, P.O. Central University, Hyderabad, 500 046, India

    SANJEEV PRAN MAHANTA & PRADEEPTA KUMAR PANDA

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  1. SANJEEV PRAN MAHANTA
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  2. PRADEEPTA KUMAR PANDA
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Correspondence to PRADEEPTA KUMAR PANDA.

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MAHANTA, S.P., PANDA, P.K. Interesting reactivity of diketones with pyrrole under acidic condition. J Chem Sci 123, 593–599 (2011). https://doi.org/10.1007/s12039-011-0128-x

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