化学
邻苯二甲酰亚胺
邻苯二甲酰亚胺
亲核酰基取代反应
酰亚胺
酰化
有机化学
药物化学
催化作用
作者
Robert N. Enright,Jeffrey L. Grinde,Lincoln Wurtz,Matthew Paeth,Tekoa R. Wittman,Emily R. Cliff,Yessra T. Sankari,Lucas T. Henningsen,Chuchen Tan,Joseph D. Scanlon,Patrick H. Willoughby
出处
期刊:Tetrahedron
[Elsevier]
日期:2016-10-01
卷期号:72 (41): 6397-6408
被引量:12
标识
DOI:10.1016/j.tet.2016.08.041
摘要
We found that N-acyl phthalimides and several N-acylated azoles are capable of reacting with aldehydes to form O-acyl-N,O-acetals in an apparent amide CN bond insertion. In the context of N-acyl phthalimides, the reaction is mediated by substoichiometric amounts of sodium iodide and potassium phthalimide. DFT computations supported a proposed mechanism and provided insights into the effect of the alkali metal additive. This strategy could be used to prepare a myriad of N,O-acetals from a range of aldehydes. A one-pot procedure was also developed in which N-acyl phthalimide was generated in situ prior to forming the N,O-acetal product. The one-pot strategy was used to demonstrate that activated amides derived from imidazole, pyrazole, (benzo)triazole, and tetrazole are also amenable substrates. Collectively, these studies provide an approach to the synthesis of a variety of N,O-acetals under mild conditions from inexpensive starting materials.
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