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Paper | Regular issue | Vol 34, No. 5, 1992, pp.1055-1063
Published online, 1st January, 1970
DOI: 10.3987/COM-92-5999
Synthesis of 2,3-Fused Quinolines from 3-Substituted Quinoline 1-Oxides. Part 1.

Yutaka Miura,* Sakae Takaku, Yasuo Fujimura, and Masatomo Hamana

*Exploratory Laboratories, Chugai Pharmaceutical Co., Ltd., 1-135 Komakado, Gotenba, Shizuoka 412, Japan

Abstract

3-(2-Bromoethyltosylamino)quinoline 1-oxide (4) reacted with TsCl-NH4OH and TsCl-K2CO3 to afford the 2-aminoquinoline (5) and the 2-quinolinone (8). Cyclization of 5 and 8 under basic conditions gave the piperazino-quinoline (6) and the morpholino-quinoline (9). Similar reactions of 3-(2-bromoethoxy)quinoline 1-oxide (13) in the presence of TsCl gave also the 2-aminoquinoline (14) and the 2-hydroxyquinoline (16), but accompanied with fair amounts of by-products (15 and, 15 and 17). Cyclization of 14 and 16 gave the morpholino-quinoline (18) and the 1,4-dioxano-quinoline (19) in somewhat lower yields.