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Instant Macrocyclizations via Multicomponent Reactions
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2023-08-19 , DOI: 10.1021/acs.joc.3c01379
Michael Fragkiadakis 1 , Paraskevi-Kleio Anastasiou 1 , Marios Zingiridis 1 , Marios E Triantafyllou-Rundell 2 , Atilio Reyes Romero 3, 4 , Constantinos C Stoumpos 2 , Constantinos G Neochoritis 1
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2023-08-19 , DOI: 10.1021/acs.joc.3c01379
Michael Fragkiadakis 1 , Paraskevi-Kleio Anastasiou 1 , Marios Zingiridis 1 , Marios E Triantafyllou-Rundell 2 , Atilio Reyes Romero 3, 4 , Constantinos C Stoumpos 2 , Constantinos G Neochoritis 1
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Macrocycles fascinate chemists due to both their structure and their applications. However, we still lack efficient and sustainable synthetic methods, giving us straightforward access to them. Herein, a rapid macrocyclization utilizing a two-step, one-pot approach based on orthogonal multicomponent reaction (MCR) tactics is introduced. This synthetic protocol, which is based on Ugi and Groebke–Blackburn–Bienaymé reactions with isocyanides tethered to alkyl tosylates, yields medium sized macrocycles that are otherwise difficult to achieve. Single crystal structures reveal conformational reorganization via intramolecular hydrogen bonding, and modeling studies profile the synthesized libraries.
中文翻译：
通过多组分反应进行即时大环化
大环化合物因其结构和应用而令化学家着迷。然而，我们仍然缺乏有效且可持续的合成方法，无法直接获取它们。在此，介绍了利用基于正交多组分反应（MCR）策略的两步一锅方法的快速大环化。该合成方案基于 Ugi 和 Groebke-Blackburn-Bienaymé 反应，异氰化物与甲苯磺酸烷基酯相连，可产生中等大小的大环化合物，而这是其他方法难以实现的。单晶结构揭示了通过分子内氢键的构象重组，建模研究对合成的库进行了分析。
更新日期：2023-08-19
中文翻译：
通过多组分反应进行即时大环化
大环化合物因其结构和应用而令化学家着迷。然而，我们仍然缺乏有效且可持续的合成方法，无法直接获取它们。在此，介绍了利用基于正交多组分反应（MCR）策略的两步一锅方法的快速大环化。该合成方案基于 Ugi 和 Groebke-Blackburn-Bienaymé 反应，异氰化物与甲苯磺酸烷基酯相连，可产生中等大小的大环化合物，而这是其他方法难以实现的。单晶结构揭示了通过分子内氢键的构象重组，建模研究对合成的库进行了分析。
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