Alkylation and oxidation of 6, 7-dihydro-6-methyl-5H-dibenzo (b, g)(1, 5) thiazocine. Selective oxidation of the sulfide moiety by transannular participation of the amino …

K Ohkata, K Takee, K Akiba

Index: Ohkata, Katsuo; Takee, Kohichi; Akiba, Kin-ya Bulletin of the Chemical Society of Japan, 1985 , vol. 58, # 7 p. 1946 - 1952

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Citation Number: 16

Abstract

6, 7-Dihydro-6-methyl-5H-dibenzo [b, g][1, 5] thiazocine (7) was prepared by cyclization of the corresponding amino alcohol using thionyl chloride in acetonitrile. Methylation of 7 gave N, N-dimethyl derivative (8) as the sole product. Treatment of 7 with various oxidizing reagents, however, afforded the corresponding sulfoxide (9) and/or N-oxide (13), and sulfone (14) depending on the kind of reagent. Oxidation of 7 with sodium periodate ...