5-Hydroxypent-2-enenitriles as precursors toward dihydropyranones, dienenitriles and functionalized naphthalenes

详细信息    查看全文

• 作者：Xinying Zhang ; ^{xinyingzhang@htu.cn} ; Xuefei Jia ; Nan Liu ; Xiaojie Guo ; Yunping Song ; Xuesen Fan
• 关键词：5-Hydroxypent-2-enenitriles ; Dihydropyranones ; Dienenitriles ; Functionalized naphthalenes
• 刊名：Tetrahedron
• 出版年：2013
• 出版时间：1 July, 2013
• 年：2013
• 卷：69
• 期：26
• 页码：5374-5382
• 全文大小：817 K

文摘

5-Hydroxypent-2-enenitriles were found to be precursors toward several classes of compounds with synthetic and biological interests. To be specific, upon treatment with sulfuric acid in dichloromethane and depending on the configuration of the C-C double bond and the nature of substituents attached on the C-C double bond, 5-hydroxypent-2-enenitriles could afford 5,6-dihydropyran-2-ones, 2,4-dienenitriles, or functionalized naphthalenes through intramolecular Pinner reaction, ¦Â-elimination or intramolecular Friedel-Crafts reaction, respectively.