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Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
A modular rearrangement approach toward medicinally relevant phosphinic structures
Vassilis Rogakos1, Dimitris Georgiadis, Vincent Dive
1Department of Chemistry, Laboratory of Organic Chemistry, University of Athens, Panepistimiopolis Zografou 15771, Athens, Greece.
A novel method efficiently creates medicinally important phosphinic compounds by coupling phosphorus-carbon and carbon-carbon bonds. This strategy utilizes a unique Ireland-Claisen rearrangement initiated by a phospha-Michael addition.
Area of Science:
- Organic Chemistry
- Medicinal Chemistry
- Synthetic Chemistry
Background:
- Phosphinic structures are crucial in medicinal chemistry.
- Existing methods for synthesizing phosphinic compounds can be limited in scope or practicality.
Purpose of the Study:
- To develop an unprecedented and practical method for synthesizing medicinally relevant phosphinic structures.
- To establish a novel P-C and C-C bond-forming strategy.
Main Methods:
- The core strategy involves a phospha-Michael addition of silyl phosphonites to allyl acrylates, triggering an Ireland-Claisen rearrangement.
- A versatile three-component variant was developed using phosphinic acids, acryloyl chlorides, and allylic alcohols.
Main Results:
- Successfully coupled P-C and C-C bond-forming events in a single operational sequence.
- Demonstrated the synthesis of diverse phosphinic structures with potential medicinal applications.
- Extended the protocol to a robust three-component reaction.
Conclusions:
- The developed method provides a practical and efficient route to valuable phosphinic compounds.
- This strategy offers a versatile platform for accessing complex phosphinic scaffolds for drug discovery.
- The novel coupling approach expands the synthetic toolkit in organic and medicinal chemistry.
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