Mechanically activated ring-opening reactions of N-acyl-1,2,3,4-tetrahydroisoquinolines derived from the synthesis of praziquantel intermediate

Add time:08/08/2019    Source:sciencedirect.com

An unexpected DDQ-promoted ring-opening reaction of N-chloroacetyl-tetrahydroisoquinoline under ball milling conditions was revealed during the synthesis of Praziquantel. A variety of N-acyl-tetrahydroisoquinolines were then tested to further investigate the reaction, and plausible reaction mechanism was proposed. Ball milling was demonstrated to be an efficient tool to promote this oxidative ring-opening reaction to give products in satisfactory yields with good selectivity in short reaction times.

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