A practical one-pot procedure for the synthesis of N–H isoquinolones

A practical one-pot procedure for the preparation of N–H isoquinolones has been developed. This 2-step process via C–H activation of N-alkoxyl benzamides and NaH-mediated dealkoxylation reaction has been demonstrated to be a high yielding alternative methodology for the efficient synthesis of a wide...

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Bibliographic Details
Published inTetrahedron letters Vol. 54; no. 15; pp. 2001 - 2005
Main Authors Lu, Shaonan, Lin, Yingfu, Zhong, Hongban, Zhao, Kang, Huang, Jianhui
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 10.04.2013
Elsevier
Subjects
Chemistry
Chemistry, Organic
C–H activation
Isoquinolone
N–O bond cleavage
Organometallics
Pd-catalysis
Physical Sciences
Science & Technology
C–H activation
Pd-catalysis
Organometallics
N–O bond cleavage
Isoquinolone
C-H/O-H
ACTIVATION
O BOND
ANNULATION
REACTIVITY
BOND FORMATION
ALKYNES
C-H activation
BENZAMIDES
ALPHA-PYRONES
N-O bond cleavage
ISOCOUMARINS
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Summary:A practical one-pot procedure for the preparation of N–H isoquinolones has been developed. This 2-step process via C–H activation of N-alkoxyl benzamides and NaH-mediated dealkoxylation reaction has been demonstrated to be a high yielding alternative methodology for the efficient synthesis of a wide range of representative N–H isoquiolones. In addition, the experimental precedent supported mechanism of the dealkoxylation reaction was also proposed.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2013.02.003