Synthesis of N-alkyl-octahydroisoquinolin-1-one-8-carboxamide libraries using a tandem Diels-Alder/acylation sequence
Kevin J Frankowski1, Erin E Hirt, Yibin Zeng
1KU Chemical Methodology and Library Development Center, University of Kansas, lawrence, Kansas 66046, USA.
Abstract:
A synthetic sequence was developed in which a diene containing an attached secondary amine was reacted with maleic anhydride to afford the title structures in one step. The reaction involves a Diels-Alder reaction combined with a transacylation reaction of the imide group. A series of six scaffolds was constructed using this methodology. Each scaffold was subsequently reacted with 12 amines to afford a library containing 72 compounds.
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