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Paper | Regular issue | Vol 32, No. 8, 1991, pp.1579-1586
Published online, 1st January, 1970
DOI: 10.3987/COM-91-5788
Reactions of 3-Substituted Quinoline 1-Oxides with Acylating Agents

Yutaka Miura,* Sakae Takaku, Yoshiharu Nawata, and Masatomo Hamana

*Exploratory Laboratories, Chugai Pharmaceutical Company, Ltd., 135, 1-Chome Komakado, Gotemba, Shizuoka 412-8513, Japan

Abstract

Reactions of 3-fluoro- (1a), 3-bromo- (1b), 3-methyl- (1c), 3-methoxy- (1d) and 3-acetamidoquinoline 1-oxides (1e) with acylating agents (POCl3, Ac2O, TsCl and PhCOCl) were examined (Table). While only 2-substituted quinolines were obtained from 1a and 1b, fair amounts of 4-substituted products were formed in reactions of 1d, the sole formation of the 4-acetoxyquinoline (6) with Ac2O being the most significant result. 2-Chloroquinolines, 4-chloroquinolines and 2-tosyloxyquinolines were formed (and sometimes predominate) in addition to 2-quinolinones in reactions with TsCl.