Synthesis of spiro compounds via three-component reaction of aldimines, electron-deficient alkynes a

• 作 者: Jing Zhang Chao-Guo Yan
• 机 构: College of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou 225002, China
• 出 处: 中国化学会全国第十一届有机合成化学学术研讨会
• 发表日期: 2014年5期
• 关键词: multicomponent reaction spiro compound electron-deficient alkyne

In the past decades, the chemistry of Huisgens 1,4-dipoles, which can be generated in situ from addition reaction of nitrogen-containing heterocycles such as pyridine, isoquinoline, imidazole and benzothiazole to electron-deficient atkynes have attracted much attentions of organic chemists, especially from the advantage point of heterocyclic synthesis.1,2 Many elegant domino reactions reactions were successfully developed on the basis of the subsequent interception of the zwitterions with versatile nucleophilie and electrophilic reagents.3-6Aldimines, which have similar structural scaffold to nitrogen-containing heterocycles such as pyridine and isoquinoline, can also act as nucleophiles to react with electron-deficient alkynes to form Huisgens 1,4-dipoles.We have developed an interesting three-component reaction of a, β-unsaturated N-arylaldirnines or aldimines with dialkyl acetylenedicarboxylates and isatins.This reaction not only provides a convenient synthetic procedure for the preparation of structurally diverse 2,3-dihydrospiro[indoline-3,6-[1,3]oxazines]-4,5-dicarboxylates in high yields, but also opens a new potentially applications of the aldimines in organic synthetic chemistry.Other cyclic diketones such as acenaphthenequinone, benzoquinone, naphthalene-1,4-dione can be used in the reactions.