Tetrahedron

Large-scale synthesis of new cyclazines, 5-thia-1, 8b-diazaacenaphthylene-3-carboxylic acid derivatives having the peripheral 12π-electron ring system

…, K Tomimatsu, K Hamamura, M Takatani, M Wakimasu

Index: Ikemoto, Tomomi; Kawamoto, Tetsuji; Wada, Hiroki; Ishida, Toru; Ito, Tatsuya; Isogami, Yasushi; Miyano, Yoshiko; Mizuno, Yukio; Tomimatsu, Kiminori; Hamamura, Kazumasa; Takatani, Muneo; Wakimasu, Mitsuhiro Tetrahedron, 2002 , vol. 58, # 3 p. 489 - 493

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Citation Number: 13

Abstract

The 5-thia-1, 8b-diazaacenaphthylenes (2 and its ester, 8) are new cyclazines, in which a paramagnetic ring is present in the peripheral 12π-electron ring system. Three convenient methods of preparing 8 have been developed. One involved thioglycolation of a new compound, 5-fluoroimidazo [1, 2-a] pyridine (6b), followed by the Duff reaction gave 8 in 64% yield without chromatographic purification.