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

Michiyasu Nakao; Akihito Nakamura; Tomoyuki Takesue; Syuji Kitaike; Hiro-O Ito; Shigeki Sano

doi:10.1055/a-2148-9433

SynOpen, Inhaltsverzeichnis

CC BY 4.0 · SynOpen 2023; 07(03): 394-400
DOI: 10.1055/a-2148-9433

paper

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

Michiyasu Nakao

^aGraduate School of Pharmaceutical Sciences, Tokushima University, Sho-machi, Tokushima 770-8505, Japan

,

Akihito Nakamura

^aGraduate School of Pharmaceutical Sciences, Tokushima University, Sho-machi, Tokushima 770-8505, Japan

,

Tomoyuki Takesue

^aGraduate School of Pharmaceutical Sciences, Tokushima University, Sho-machi, Tokushima 770-8505, Japan

,

Syuji Kitaike

^aGraduate School of Pharmaceutical Sciences, Tokushima University, Sho-machi, Tokushima 770-8505, Japan

,

Hiro-O Ito

^bDepartment of Preventive Dentistry, Graduate School of Biomedical Sciences, Tokushima University, Kuramoto-cho, Tokushima 770-8504, Japan

,

Shigeki Sano∗

^aGraduate School of Pharmaceutical Sciences, Tokushima University, Sho-machi, Tokushima 770-8505, Japan

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Abstract

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Abstract

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.

Key words

OPA method - isoindoles - ortho-phthalaldehyde - 9,10-dihydro-9-oxa-10-phosphaphenanthrene 10-oxide - primary amines - isoindolin-1-ones - ring-opening - methanolysis

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References

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