Multicomponent Assembly and Diversification of Novel Heterocyclic Scaffolds Derived from 2-Arylpiperidines

被引：35

作者：

Hardy, Simon ^{[1
]}

Martin, Stephen F. ^{[1
]}

机构：

[1] Univ Texas Austin, Dept Chem & Biochem, Texas Inst Drug & Diagnost Dev, Austin, TX 78712 USA

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 12期

关键词：

DRUG DISCOVERY; COMBINATORIAL; CYCLIZATION; DIVERSE; DESIGN;

D O I：

10.1021/ol201010s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：3102 / 3105

页数：4

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