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Paper | Regular issue | Vol 63, No. 3, 2004, pp.591-608
Published online, 26th December, 2003
DOI: 10.3987/COM-03-9961
■ Reaction of [1,4]Benzodioxinopyridazines with Sodium Methoxide and Amines

Etsuo Oishi,* Chitose Sugiyama, Ken-ichi Iwamoto, and Ikuo Kato

*Division of Environmental Health Sciences, Graduate of School of Nutritional & Environmental Sciences, University of Shizuoka, 52-1 Yada, Shizuoka 422-8526, Japan

Abstract

The reaction of 1-chloro (3), 1-methylsulfonyl (7) [1,4]benzodioxino[2,3-d]pyridazine and 4-chloro[1,4]benzodioxino[2,3-c]pyridazine (4) with sodium methoxide afforded dioxin ring-opened pyridazines (14 — 16) and ring-cyclized pyridazines (9, 10), while their reaction with amines [n-butylamine (8a), cyclohexylamine (8b), morpholine (8c), piperidine (8d), pyrrolidine (8e), hydrazine (8f) and aniline (8g)] afforded 1-substituted [1,4]benzodioxino[2,3-d]pyridazines (18), 4-substituted [1,4]benzodioxino[2,3-c]pyridazines (19) and/or 2-hydroxyphenoxypyridazines (20 — 22).