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Paper | Special issue | Vol 49, No. 1, 1998, pp.121-126
Published online, 1st January, 1970
DOI: 10.3987/COM-97-7978
Photochemical Rearrangements of 1-Acetyl-1,2-dihydroquinoline-2-carbonitriles to the 3,1-Benzoxazines and Cycloprop[b]indoles

Masazumi Ikeda,* Saeko Matsugashita, Chika Yukawa, and Takayuki Yakura

*Kyoto Pharmaceutical University, Misasagi, Yamashina, Kyoto 607, Japan

Abstract

Irradiation of 1-acetyl-1,2-dihydroquinoline-2-carbonitrile (1) in ether gave the 3,1-benzoxazine (3b), while the 4-methyl congener (2) in either ether or ethanol gave the 3,1-benzoxazine (4b) and the cycloprop[b]indole (7). A possible mechanism for the formation of these products is also discussed.