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Beilstein J Org Chem. 2012;8:1293-302. Epub 2012 Aug 15.

Exploring chemical diversity via a modular reaction pairing strategy.

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Department of Chemistry, The University of Kansas, 1251 Wescoe Hall Drive, Lawrence, KS 66045-7582, USA.


The efficient synthesis of an 80-member library of unique benzoxathiazocine 1,1-dioxides by a microwave-assisted, intermolecular nucleophilic aromatic substitution (S(N)Ar) diversification pathway is reported. Eight benzofused sultam cores were generated by means of a sulfonylation/S(N)Ar/Mitsunobu reaction pairing protocol, and subsequently diversified by intermolecular S(N)Ar with ten chiral, non-racemic amine/amino alcohol building blocks. Computational analyses were employed to explore and evaluate the chemical diversity of the library.


benzoxathiazocine 1,1-dioxides; chemical diversity; informatics; nucleophilic aromatic substitution (SNAr); sultams

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