Synthesis of new quinolone antibiotics utilizing azetidine derivatives obtained from 1-azabicyclo [1.1. 0] butane

Y Ikee, K Hashimoto, M Kamino, M Nakashima…

Index: Ikee, Yoshifumi; Hashimoto, Kana; Kamino, Mai; Nakashima, Masaaki; Hayashi, Kazuhiko; Sano, Shigeki; Shiro, Motoo; Nagao, Yoshimitsu Chemical and Pharmaceutical Bulletin, 2008 , vol. 56, # 3 p. 346 - 356

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Citation Number: 11

Abstract

A series of 3-sulfenylazetidine derivatives 5a—f were synthesized via the ring-opening reactions of 1-azabicyclo [1.1. 0] butane (ABB, 3) with thiols 4a—f in 50—92% yields. Treatment of ABB (3) with aromatic amines 9a—e and dibenzylamine (9f) in the presence of Mg (ClO 4) 2 afforded the corresponding 3-aminoazetidine derivatives 10a—f in 24—65% yields. N-Benzyl-3-bromoazetidine (13), which was obtained by the reaction of ABB (3) ...