Synthesis of Novel Phosphorus-Substituted Stable Isoindoles by a Three-Component Coupling Reaction of ortho-Phthalaldehyde, 9,10-Dihydro-9-oxa-10-phosphaphenanthrene 10-Oxide, and Primary Amines

A three-component coupling reaction of ortho-phthalaldehyde, 9,10-dihydro-9-oxa-10-phosphaphenanthrene 10-oxide, and various primary amines readily afforded novel phosphorus-substituted stable isoindoles in good to excellent yields. The importance of the reversible ring-opening of 9,10-dihydro-9-oxa...

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Bibliographic Details
Published in:SynOpen (2017) 2023-08, Vol.7 (3), p.394-400
Main Authors: Nakao, Michiyasu, Nakamura, Akihito, Takesue, Tomoyuki, Kitaike, Syuji, Ito, Hiro-O, Sano, Shigeki
Format: Article
Language:English
Subjects:
9,10-dihydro-9-oxa-10-phosphaphenanthrene 10-oxide
isoindoles
isoindolin-1-ones
methanolysis
OPA method
ortho-phthalaldehyde
primary amines
ring-opening
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Summary:A three-component coupling reaction of ortho-phthalaldehyde, 9,10-dihydro-9-oxa-10-phosphaphenanthrene 10-oxide, and various primary amines readily afforded novel phosphorus-substituted stable isoindoles in good to excellent yields. The importance of the reversible ring-opening of 9,10-dihydro-9-oxa-10-phosphaphenanthrene 10-oxide by methanolysis in the three-component coupling reaction became apparent.
ISSN:2509-9396
2509-9396
DOI:10.1055/a-2148-9433