Brønsted Acid Triggers [6/7 + 1] Cascade Cyclization by N-Alkyl Amine C(sp3)–N Cleavage: Mild Synthesis of Benzo[1,4]oxazepane and Dihydrobenzo[1,5]oxazocine,The Journal of Organic Chemistry

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Brønsted Acid Triggers [6/7 + 1] Cascade Cyclization by N-Alkyl Amine C(sp3)–N Cleavage: Mild Synthesis of Benzo[1,4]oxazepane and Dihydrobenzo[1,5]oxazocine
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2024-09-01 , DOI: 10.1021/acs.joc.4c01827
Lu Yin ₁ , Zhou Zhang ₁ , Shuntao Huang ₁ , Zhuoyu Wang ₁ , Chao Huang _{1,

2}

Affiliation

A catalyst-free mild synthesis was reported to produce medium-ring oxazepane and oxazocine derivatives from aminomaleimides and N-alkyl amines. The substrate and acidic additives were employed to cleave the C(sp³)–N bond as a one-carbon synthon for C–C and C–O coupling, thus facilitating the [n + 1] cascade cyclization reaction, which enabled the construction of seven- and eight-membered N,O-heterocycles at room temperature. The method exhibits abroad substrate scope and remarkable tolerance toward various functional groups (seven-membered 28 examples, eight-membered 8 examples, and activated N-alkyl amine 12 examples) and utilization of natural products (2 examples).

中文翻译：

布朗斯台德酸通过 N-烷基胺 C(sp3)–N 裂解引发 [6/7 + 1] 级联环化：苯并[1,4]氧氮杂环庚烷和二氢苯并[1,5]氧氮辛的温和合成

据报道，无催化剂温和合成可以从氨基马来酰亚胺和N-烷基胺生产中环氧杂氮杂环庚烷和恶佐辛衍生物。采用底物和酸性添加剂裂解C(sp ³ )–N键作为C–C和C–O偶联的一碳合成子，从而促进[ n + 1]级联环化反应，从而实现了构建室温下的七元和八元N ， O-杂环。该方法表现出广泛的底物范围和对各种官能团（七元28例、八元8例、活化N-烷基胺12例）和天然产物利用（2例）的显着耐受性。

更新日期：2024-09-01

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