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Exploring chemical diversity via a modular reaction pairing strategy

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Author(s): Joanna K. Loh | Sun Young Yoon | Thiwanka B. Samarakoon | Alan Rolfe | Patrick Porubsky | Benjamin Neuenswander | Gerald H. Lushington | Paul R. Hanson

Journal: Beilstein Journal of Organic Chemistry
ISSN 1860-5397

Volume: 8;
Issue: 1;
Start page: 1293;
Date: 2012;
Original page

Keywords: benzoxathiazocine 1 | 1-dioxides | chemical diversity | informatics | nucleophilic aromatic substitution (SNAr) | sultams

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