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Exploring chemical diversity via a modular reaction pairing strategy.
Joanna K Loh1, Sun Young Yoon, Thiwanka B Samarakoon
1Department of Chemistry, The University of Kansas, 1251 Wescoe Hall Drive, Lawrence, KS 66045-7582, USA.
Beilstein Journal of Organic Chemistry
|September 29, 2012
Summary
This study reports an efficient synthesis of 80 unique benzoxathiazocine 1,1-dioxides using microwave-assisted reactions. The novel compounds were created through a sulfonylation/S(N)Ar/Mitsunobu protocol and diversified using chiral building blocks.
Area of Science:
- Organic Chemistry
- Medicinal Chemistry
- Synthetic Chemistry
Background:
- Benzoxathiazocine 1,1-dioxides are a class of heterocyclic compounds with potential biological activity.
- Developing efficient synthetic routes to diverse libraries of these compounds is crucial for drug discovery.
- Exploring novel diversification strategies is key to accessing a wide range of chemical structures.
Purpose of the Study:
- To develop an efficient microwave-assisted synthesis for a library of benzoxathiazocine 1,1-dioxides.
- To generate a diverse library of 80 unique compounds.
- To explore the chemical diversity of the synthesized library using computational methods.
Main Methods:
- Microwave-assisted synthesis
- Intermolecular nucleophilic aromatic substitution (S(N)Ar) reactions
- Sulfonylation/S(N)Ar/Mitsunobu reaction pairing protocol
- Diversification with chiral amine/amino alcohol building blocks
- Computational analyses
Main Results:
- Efficient synthesis of an 80-member library of unique benzoxathiazocine 1,1-dioxides.
- Generation of eight benzofused sultam cores.
- Successful diversification using ten chiral, non-racemic amine/amino alcohol building blocks.
- Evaluation of chemical diversity through computational analyses.
Conclusions:
- The reported microwave-assisted S(N)Ar pathway provides an efficient method for synthesizing diverse benzoxathiazocine 1,1-dioxide libraries.
- The combination of sulfonylation, S(N)Ar, and Mitsunobu reactions enables the construction of complex heterocyclic cores.
- Computational analysis aids in understanding and evaluating the chemical space explored by the library.
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