Multicomponent, Mannich-type assembly process for generating novel, biologically-active 2-arylpiperidines and derivatives.
Multicomponent, Mannich-type assembly process for generating novel, biologically-active 2-arylpiperidines and derivatives.
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DOI：
10.1016/j.tet.2014.06.045
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发表时间：
2014-10-07
期刊：
影响因子：
2.1
通讯作者：
Martin, Stephen F.
中科院分区：
文献类型：
--
作者：
Hardy, Simon;Martin, Stephen F.
关键词：
以商业上可获得的溴苯甲醛为起始的多组分Mannich类型的组装过程与涉及硝酮和氨甲亚胺叶立德的[3+2]偶极环加成反应进行了测序，以生成基于2-芳基哌啶亚基的稠合双环支架的集合。4-戊烯基既是Mannich反应中的活化剂，又是易被裂解的胺保护基团，它的使用允许通过哌啶N-官能化和芳基溴的交叉偶联来制备亚文库。其中许多衍生物显示了以前没有与该亚结构相关的生物活性。还开发了能够使这些支架快速转化为新的多环二氢喹唑啉-2-酮、2-亚氨基-1，3-苯并噻嗪、二氢异喹啉-3-酮和桥联四氢喹啉的方法。
A multicomponent, Mannich-type assembly process commencing with commercially available bromobenzaldehydes was sequenced with [3+2] dipolar cycloaddition reactions involving nitrones and azomethine ylides to generate collections of fused, bicyclic scaffolds based on the 2-arylpiperidine subunit. Use of the 4-pentenoyl group, which served both as an activator in the Mannich-type reaction and a readily-cleaved amine protecting group, allowed sub-libraries to be prepared through piperidine N-functionalization and cross-coupling of the aryl bromide. A number of these derivatives displayed biological activities that had not previously been associated with this substructure. Methods were also developed that allowed rapid conversion of these scaffolds to novel, polycyclic dihydroquinazolin-2-ones, 2-imino-1,3-benzothiazinanes, dihydroisoquinolin-3-ones and bridged tetrahydroquinolines.
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DOI：
10.1073/pnas.0503647102
发表时间：
2005-11-29
影响因子：
11.1
作者：
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通讯作者：
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影响因子：
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影响因子：
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