Synthesis of Sterically Protected Isoindoles from ortho-Phthalaldehyde

Michiyasu Nakao; Nanako Nishikiori; Akihito Nakamura; Murasaki Miyagi; Nao Shibata; Syuji Kitaike; Makoto Fukui; Hiro-O Ito; Shigeki Sano

doi:10.1055/s-0036-1591932

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CC BY ND NC 4.0 · SynOpen 2018; 02(01): 0050-0057
DOI: 10.1055/s-0036-1591932

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Synthesis of Sterically Protected Isoindoles from ortho-Phthalaldehyde

Authors

Michiyasu Nakao

^aGraduate School of Pharmaceutical Sciences, Tokushima University, Sho-machi, Tokushima 770-8505, Japan Email: ssano@tokushima-u.ac.jp
Nanako Nishikiori

^aGraduate School of Pharmaceutical Sciences, Tokushima University, Sho-machi, Tokushima 770-8505, Japan Email: ssano@tokushima-u.ac.jp
Akihito Nakamura

^aGraduate School of Pharmaceutical Sciences, Tokushima University, Sho-machi, Tokushima 770-8505, Japan Email: ssano@tokushima-u.ac.jp
Murasaki Miyagi

^aGraduate School of Pharmaceutical Sciences, Tokushima University, Sho-machi, Tokushima 770-8505, Japan Email: ssano@tokushima-u.ac.jp
Nao Shibata

^aGraduate School of Pharmaceutical Sciences, Tokushima University, Sho-machi, Tokushima 770-8505, Japan Email: ssano@tokushima-u.ac.jp
Syuji Kitaike

^aGraduate School of Pharmaceutical Sciences, Tokushima University, Sho-machi, Tokushima 770-8505, Japan Email: ssano@tokushima-u.ac.jp
Makoto Fukui

^bDepartment of Preventive Dentistry, Institute of Biomedical Sciences, Tokushima University Graduate School, 3-18-15, Kuramoto-cho, Tokushima 770-8504, Japan
Hiro-O Ito

^bDepartment of Preventive Dentistry, Institute of Biomedical Sciences, Tokushima University Graduate School, 3-18-15, Kuramoto-cho, Tokushima 770-8504, Japan
Shigeki Sano*

^aGraduate School of Pharmaceutical Sciences, Tokushima University, Sho-machi, Tokushima 770-8505, Japan Email: ssano@tokushima-u.ac.jp

Abstract

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Abstract

o-Phthalaldehyde (OPA) reacts with O-protected tris(hydroxyalkyl)aminomethanes in the presence of 1-propanethiol to afford a novel class of stable isoindoles. Steric protection provided by the bulkiness of C ₃-symmetric primary amines derived from tris(hydroxymethyl)aminomethane could be significant for the stabilization of 1-alkylthio-2-alkyl-substituted isoindoles derived from OPA. A plausible reaction mechanism is proposed to explain the formation of the isoindole and an isoindolin-1-one by-product.

Key words

o-phthalaldehyde - isoindole - steric protection - isoindolin-1-one

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Supplementary Material

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