Multicomponent assembly and diversification of novel heterocyclic scaffolds derived from 2-arylpiperidines
Simon Hardy1, Stephen F Martin
1Department of Chemistry and Biochemistry, The Texas Institute for Drug and Diagnostic Development, The University of Texas at Austin, Austin, Texas 78712, USA.
Abstract:
A collection of structurally diverse, polyheterocyclic scaffolds comprising a 2-arylpiperidine subunit were synthesized using a Mannich-type multicomponent assembly process, followed by appropriately sequenced ring-forming reactions. An improved procedure for removal of N-4-pentenoyl groups was developed; one-pot sequences for tandem urea/thiourea formation and cyclization and tandem enolate arylation/alkylation were discovered. A novel entry to bridged tetrahydroquinoline scaffolds exploiting A(1,3) strain was also invented. Derivatization of several scaffolds was achieved by cross-coupling and N-functionalization.
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