Synthesis of 4-imidoyl-, 4-oxiranyl- and 4-propargyloxyphenyl-substituted β-lactam building blocks,Journal of Heterocyclic Chemistry

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Synthesis of 4-imidoyl-, 4-oxiranyl- and 4-propargyloxyphenyl-substituted β-lactam building blocks
Journal of Heterocyclic Chemistry ( IF 2.0 ) Pub Date : 2022-10-30 , DOI: 10.1002/jhet.4597
Sari Deketelaere ₁ , Gurkirat Kaur _{1,

2} , Nicola Piens ₁ , Daan Deturck ₁ , Robin Depestel ₁ , Kristof Van Hecke ₃ , Christian V. Stevens ₁ , Vipan Kumar ₂ , Matthias D'hooghe ₁

Affiliation

In this study, the preparation of 4-imidoyl-, 4-oxiranyl-, and 4-propargyloxyphenyl-substituted β-lactams as versatile building blocks in heterocyclic chemistry was realized. Efforts were made to deploy these polyvalent compounds for ensuing cyclization reactions en route to new bi- or polycyclic frameworks, which, in the case of a 3-chloro-4-propargyloxyphenyl-β-lactam substrate, enabled the preparation of an unprecedented β-lactam-fused benzotriazolo-oxazocane scaffold. The chemical structure of the latter polyheterocycle was unequivocally secured by means of X-ray analysis.

中文翻译：

4-imidoyl-、4-oxiranyl- 和 4-propargyloxyphenyl-取代的 β-内酰胺结构单元的合成

在这项研究中，实现了 4-亚胺酰基-、4-环氧乙烷基-和 4-炔丙基氧基苯基取代的 β-内酰胺作为杂环化学中多功能构建单元的制备。人们努力部署这些多价化合物，以确保在形成新的双环或多环框架的过程中发生环化反应，在 3-chloro-4-propargyloxyphenyl-β-lactam 底物的情况下，能够制备出前所未有的 β-内酰胺融合的苯并三唑并恶唑烷支架。后一种多杂环的化学结构通过 X 射线分析明确确定。

更新日期：2022-10-30

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