Abstract
Multicomponent reactions (MCRs) generate multiple bonds in a single reaction process, which is highly efficient to construct relatively complex molecules. Conducting post-MCR modification reactions further increases the molecular complexity and diversity. MCR has become a powerful approach to make drug-like molecules in lead generation chemistry. In fluorous MCR (F-MCR), one of the starting materials is attached to a fluorous tag and used as the limiting agent. After the MCR, the fluorous component is fished out from the reaction mixture and used for post-MCR modifications. The fluorous tag can be finally removed in traceless fashion by displacement or cyclization reactions. Unique fluorous technology such as fluorous solid-phase extraction (F-SPE) facilitates the separation process. Other techniques such as microwave irradiation and plate-to-plate SPE can also be used to make the F-MCR even more efficient. Syntheses of unique heterocyclic and natural product-like library scaffolds using Ugi/de-Boc/cyclization, MCR/Suzuki coupling, and [3+2] cycloaddition/de-tag/cyclization protocols are described in this paper.
Keywords: Diversity-oriented synthesis, drug-like molecules, fluorous synthesis, library scaffolds, microwave reactions, multicomponent reactions, solid-phase extraction
Combinatorial Chemistry & High Throughput Screening
Title: Fluorous-Enhanced Multicomponent Reactions for Making Drug-Like Library Scaffolds
Volume: 10 Issue: 3
Author(s): Wei Zhang
Affiliation:
Keywords: Diversity-oriented synthesis, drug-like molecules, fluorous synthesis, library scaffolds, microwave reactions, multicomponent reactions, solid-phase extraction
Abstract: Multicomponent reactions (MCRs) generate multiple bonds in a single reaction process, which is highly efficient to construct relatively complex molecules. Conducting post-MCR modification reactions further increases the molecular complexity and diversity. MCR has become a powerful approach to make drug-like molecules in lead generation chemistry. In fluorous MCR (F-MCR), one of the starting materials is attached to a fluorous tag and used as the limiting agent. After the MCR, the fluorous component is fished out from the reaction mixture and used for post-MCR modifications. The fluorous tag can be finally removed in traceless fashion by displacement or cyclization reactions. Unique fluorous technology such as fluorous solid-phase extraction (F-SPE) facilitates the separation process. Other techniques such as microwave irradiation and plate-to-plate SPE can also be used to make the F-MCR even more efficient. Syntheses of unique heterocyclic and natural product-like library scaffolds using Ugi/de-Boc/cyclization, MCR/Suzuki coupling, and [3+2] cycloaddition/de-tag/cyclization protocols are described in this paper.
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Cite this article as:
Zhang Wei, Fluorous-Enhanced Multicomponent Reactions for Making Drug-Like Library Scaffolds, Combinatorial Chemistry & High Throughput Screening 2007; 10 (3) . https://dx.doi.org/10.2174/138620707780126697
DOI https://dx.doi.org/10.2174/138620707780126697 |
Print ISSN 1386-2073 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5402 |
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