An unexpected and direct synthesis of ethyl 2,4-bis(chloromethyl)-6-iodoquinoline-3-carboxylate ( 3 ) from the chlorotrimethylsilane (TMSCl)-promoted Friedländer reaction between 1-(2-amino-5-iodophenyl)ethanone ( 2 ) and ethyl 4-chloro-3-oxobutanoate has been disclosed. As a versatile and attractive building block, a synthetic application of the poly-functionalized quinoline 3 in the successive Williamson ether synthesis with various phenols and in situ ester hydrolysis reaction has been achieved and the corresponding 2,4-bis(aroxymethyl)quinoline-3-carboxylic acids ( 5a-k ) were obtained in good yields of 71–86%.

This study demonstrates a novel, efficient synthesis of ethyl 2,4-bis(chloromethyl)-6-iodoquinoline-3-carboxylate, a versatile building block, with potential applications in various synthetic processes.

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An unexpected synthesis and application of ethyl 2,4-bis(chloromethyl)-6-iodoquinoline-3-carboxylate

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