Electronic and steric effects on the intramolecular Schmidt reaction of alkyl azides with secondary benzyl alcohols

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• 作者：Xiaowei Sun ; Chengzhe Gao ; Fan Zhang ; Zhuang Song ; Lingyi Kong ; Xiaoan Wen ; Hongbin Sun
• 关键词：Intramolecular Schmidt reaction ; Alkyl azide ; Secondary benzyl alcohol ; Dihydrobenzotriazine
• 刊名：Tetrahedron
• 出版年：21 January, 2014
• 年：2014
• 卷：70
• 期：3
• 页码：643-649
• 全文大小：585 K

文摘

The intramolecular Schmidt reaction of simple azido secondary benzyl alcohols has been realized for the first time. Investigation of the electronic and steric effects of the substrates on the product outcome was conducted. Unique intramolecular Schmidt rearrangements were observed with the formation of a cinnamaldehyde derivative and aryl aldehydes, respectively. Using this protocol, an efficient synthesis of dihydrobenzotriazine derivatives was achieved. Moreover, a practical approach to 2-aryl-1-pyrrolines was also accessed.