Synthesis of Pyrido[2,3-e]pyrrolo[1,2-a]pyrazine Derivatives via Tandem Iminium Cyclization and Smiles Rearrangement

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• 作者：Jinbao Xiang ; Hongxiang Xie ; Dongsheng Wen ; Qun Dang ; Xu Bai
• 刊名：Journal of Organic Chemistry
• 出版年：2008
• 出版时间：April 18, 2008
• 年：2008
• 卷：73
• 期：8
• 页码：3281 - 3283
• 全文大小：53K
• 年卷期：v.73,no.8(April 18, 2008)
• ISSN：1520-6904

文摘

The tandem iminium cyclization and Smiles rearrangementof pyridinyloxyacetaldehyde 1 and a primary amine generateda novel pyrido[2,3-e]pyrrolo[1,2-a]pyrazine scaffold. TFAwas discovered to be an efficient catalyst in the reactionswith aromatic amines, whereas TiCl₄ was found to besuperior in the case of aliphatic amines. This methodologyproved to be efficient in the preparation of a library ofdiversified pyrido[2,3-e]pyrrolo[1,2-a]pyrazine derivatives.