Tandem Synthesis of 10-Dimethylaminobenzo[h]quinazolines from 2-Ketimino-1,8-bis(dimethylamino)naphthalenes via Nucleophilic Replacement of the Unactivated Aromatic NMe2 Group

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• 作者：Vladimir Y. Mikshiev ; Alexander S. Antonov ; Alexander F. Pozharskii
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：June 17, 2016
• 年：2016
• 卷：18
• 期：12
• 页码：2872-2875
• 全文大小：295K
• 年卷期：0
• ISSN：1523-7052

文摘

It has been found that 2-bromo-1,8-bis(dimethylamino)naphthalene on sequential treatment with n-BuLi and 2 equiv of the same or different aryl(hetaryl) cyanide as a result of [2 + 2 + 2] nucleophilic cascade annulation produces 10-dimethylaminobenzo[h]quinazolines, as yet unknown NMe₂/–N═ analogues of the proton sponge. It is even more convenient to use preliminarily prepared 2-ketimino-1,8-bis(dimethylamino)naphthalenes as starting material. The substitution of both peri-NMe₂ groups furnishing quinazolino[7,8-h]quinazoline derivatives is also possible. The process is remarkable by surprisingly mild nucleophilic displacement of an unactivated aromatic NMe₂ group.