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Paper | Regular issue | Vol 36, No. 5, 1993, pp.1005-1016
Published online, 1st January, 1970
DOI: 10.3987/COM-92-9259
Synthesis of 2,3-Fused Quinolines from 3-Substituted Quinoline 1-Oxides. Part II.

Yutaka Miura,* Mitsutaka Yoshida, and Masatomo Hamana

*Exploratory Laboratories, Chugai Pharmaceutical Company, Ltd., 1-135 Komakado, Gotemba, Shizuoka 412-835, Japan

Abstract

3-Bromo-4-nitroquinoline 1-oxide (1) reacted with 2-methylaminoethanol, 1-amino-2-propanol and ethylenediamine to give the corresponding 3-amino-4-nitroquinoline 1-oxides (2, 4 and 7), which readily underwent the intramolecular cyclization, upon heating with Ac2O in DMF, to afford the morpholino[2,3-b]quinolines (3 and 6) and the piperazino[2,3-b]quinoline (8). The reaction of 1 with N,N’-dimethylethylenediamine afforded directly the piperazinoquinoline (10), and that with 2-aminoethanethiol gave the thiomorpholino[2,3-b]quinoline (11) and its 10-oxide (12).