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Synthesis of Tryptamines through a Novel Brønsted Acid Mediated Tandem Reaction Initiated by α-Iminol Rearrangement of Transient 2-Substituted 2-Hydroxycyclobutylimines
Synthesis ( IF 2.6 ) Pub Date : 2020-11-16 , DOI: 10.1055/s-0040-1706587 Angelo Frongia 1 , Lorenzo Serusi 1 , Federico Cuccu 1 , Francesco Secci 1 , David J. Aitken 2
中文翻译:
通过瞬时2-取代的2-羟基环丁基亚胺的α-亚氨基重排引发的新型布朗斯台德酸介导的串联反应合成色胺
更新日期:2020-11-17
Synthesis ( IF 2.6 ) Pub Date : 2020-11-16 , DOI: 10.1055/s-0040-1706587 Angelo Frongia 1 , Lorenzo Serusi 1 , Federico Cuccu 1 , Francesco Secci 1 , David J. Aitken 2
Affiliation
A novel Brønsted acid promoted condensation reaction between a primary aniline and 2-hydroxycyclobutanone provides access to diverse tryptamine derivatives in moderate to good yields. The proposed mechanism involves an α-iminol rearrangement, ring expansion, ring closure, and a depart-and-return rearrangement process.
中文翻译:
通过瞬时2-取代的2-羟基环丁基亚胺的α-亚氨基重排引发的新型布朗斯台德酸介导的串联反应合成色胺
一种新颖的布朗斯台德酸促进伯胺与2-羟基环丁酮之间的缩合反应,可提供中等至良好收率的多种色胺衍生物。所提出的机制涉及α-亚氨基重排,环的扩展,环的闭合以及离去和返回的重排过程。