Exploring chemical diversity via a modular reaction pairing strategy

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...

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Detalles Bibliográficos
Autores principales: Loh, Joanna K, Yoon, Sun Young, Samarakoon, Thiwanka B, Rolfe, Alan, Porubsky, Patrick, Neuenswander, Benjamin, Lushington, Gerald H, Hanson, Paul R
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2012
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3458752/
https://www.ncbi.nlm.nih.gov/pubmed/23019462
http://dx.doi.org/10.3762/bjoc.8.147
Descripción
Sumario: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.

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