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An Aminocatalyzed Michael Addition/Iron-Mediated Decarboxylative Cyclization Sequence for the Preparation of 2,3,4,6-Tetrasubstituted Pyridines: Scope and Mechanistic Insights
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2017-09-22 00:00:00 , DOI: 10.1021/acs.joc.7b01789 Mateus L. Stivanin 1 , Marcelo Duarte 1 , Camila Sartori 1 , Naylil M. R. Capreti 1 , Celio F. F. Angolini 1 , Igor D. Jurberg 1
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2017-09-22 00:00:00 , DOI: 10.1021/acs.joc.7b01789 Mateus L. Stivanin 1 , Marcelo Duarte 1 , Camila Sartori 1 , Naylil M. R. Capreti 1 , Celio F. F. Angolini 1 , Igor D. Jurberg 1
Affiliation
A novel, scalable strategy for the preparation of 2,3,4,6-tetrasubstituted pyridines is described. This protocol has two steps: an aminocatalyzed addition of ketones to alkylidene isoxazol-5-ones, followed by an iron-mediated decarboxylative cyclization event. Mechanistic insights for both steps are provided based on HRMS-ESI(+) studies.
中文翻译:
氨基催化的迈克尔加成/铁介导的脱羧环化序列制备2,3,4,6-四取代的吡啶:范围和机制的见解。
描述了一种制备2,3,4,6-四取代吡啶的新颖,可扩展的策略。该方案有两个步骤:将氨基氨基催化的酮加成至亚烷基异恶唑-5-酮中,然后进行铁介导的脱羧环化反应。基于HRMS-ESI(+)研究,提供了这两个步骤的机械原理。
更新日期:2017-09-22
中文翻译:
氨基催化的迈克尔加成/铁介导的脱羧环化序列制备2,3,4,6-四取代的吡啶:范围和机制的见解。
描述了一种制备2,3,4,6-四取代吡啶的新颖,可扩展的策略。该方案有两个步骤:将氨基氨基催化的酮加成至亚烷基异恶唑-5-酮中,然后进行铁介导的脱羧环化反应。基于HRMS-ESI(+)研究,提供了这两个步骤的机械原理。