Chemoselective One-Pot Synthesis of Functionalized Amino-azaheterocycles Enabled by COware

Functionalized bicyclic amino-azaheterocycles are rapidly accessed in a one-pot cross-coupling/reduction sequence enabled by the use of COware. Incompatible reagents are physically separated in a single reaction vessel to effect two chemoselective transformationsSuzuki–Miyaura cross-coupling and he...

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Published inOrganic letters Vol. 19; no. 23; pp. 6368 - 6371
Main Authors Clohessy, Thomas A, Roberts, Alastair, Manas, Eric S, Patel, Vipulkumar K, Anderson, Niall A, Watson, Allan J. B
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 01.12.2017
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
PARAFFIN
GENERATION
CARBONYLATION
INHIBITORS
DERIVATIVES
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Summary:Functionalized bicyclic amino-azaheterocycles are rapidly accessed in a one-pot cross-coupling/reduction sequence enabled by the use of COware. Incompatible reagents are physically separated in a single reaction vessel to effect two chemoselective transformationsSuzuki–Miyaura cross-coupling and heteroarene reduction. The developed method allows access to novel heterocyclic templates, including semisaturated Hedgehog and dual PI3K/mTOR inhibitors, which show enhanced physicochemical properties compared to their unsaturated counterparts.
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content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.7b03214