Photocyclization of N-Alkoxyalkylphthalimides with Favored δ-Hydrogen Abstraction : Syntheses of Oxazolo [4, 3-α] isoindoles and Oxazolo [4, 3-α]-isoindole-1-spiro-1'-cycloalkane Ring Systems

YASUHIKO SATO; HIDEO NAKAI; MASAO WADA; HIROSHI OGIWARA; TOMISHIGE MIZOGUCHI; YOSHIHIRO MIGITA; YASUMARU HATANAKA; YUICHI KANAOKA

doi:10.1248/cpb.30.1639

YASUHIKO SATO, HIDEO NAKAI, MASAO WADA, HIROSHI OGIWARA, TOMISHIGE MIZOGUCHI, YOSHIHIRO MIGITA, YASUMARU HATANAKA, YUICHI KANAOKA

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Keywords: multicyclic spiro system

JOURNAL FREE ACCESS

1982 Volume 30 Issue 5 Pages 1639-1645

DOI https://doi.org/10.1248/cpb.30.1639

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Abstract

Photolysis of N-ω-alkoxyalkylphthalimides 1 gave the intramolecularly cyclized compounds, oxazolo [4, 3-a] isoindoles 2a-g, pyrrolo [2, 1-a] isoindoles 6i-j, oxazolo [4, 3-a]-isoindole-1-spiro-1'-cycloalkanes 2k-n and 3, 4-dihydro-2-benzazepine-1, 5 (2H)-dione 3, via δ-hydrogen abstraction and/or two-fold Norrish type II processes.

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