Regiochemical control in Diels–Alder routes to aza-anthraquinone derivatives

KT Potts, D Bhattacharjee, EB Walsh

Index: Potts, Kevin T.; Bhattacharjee, Debkumar; Walsh, Eileen B. Journal of the Chemical Society, Chemical Communications, 1984 , # 2 p. 114 - 116

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Abstract

Quinoline-and isoquinoline-5, 8-diones react with 1-methoxycyclohexa-1, 3-diene at 80° C, the former giving 8-methoxy-1-aza-anthraquinone regiospecifically and the latter 5-methoxy- 2-aza-anthraquinone regioselectively; in similar cycloadditions, substituted naphtho-and azanaphtho-quinones react with 1-dimethylamino-3-methyl-1-azabuta-1, 3-diene at room temperature forming substituted mono-and di-aza-anthraquinones in high yields with high ...