Selective Access to Sultams and Spirocyclic Sultams by the Divergent Annulations of (N‐Aryl)‐Alkynyl Sulphonamides

IF 4.4 2区 化学 Q2 CHEMISTRY, APPLIED Advanced Synthesis & Catalysis Pub Date : 2024-11-19 DOI:10.1002/adsc.202400382
Chada Raji Reddy , Anjali Rathaur , Banoth Karuna Sagar , Agnuru Theja , Amol D. Patil , Muppidi Subbarao
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Abstract

Herein, we present the first annulation reaction of (N‐aryl)‐alkynyl sulphonamides leading to sultams or spirocyclic sultams. The selective formation of aforesaid products is based on the variable reactivity, intramolecular ortho‐cyclization or dearomative ipso‐annulation, guided by the substituent on N‐aryl group of the substrate. The ortho‐annulation is mediated by electrophile, while the ipso‐annulation is promoted by the radical, enabling the functionalization (selenyl or iodo) on sultams. The synthetic potential of this method is illustrated by modifications of the functional groups present in the products obtained.

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通过(N-芳基)-炔基磺酰胺的歧化反应选择性地获得舒坦和螺环舒坦
在此,我们首次介绍了(N-芳基)-炔基磺酰胺的环化反应,该反应可生成舒坦或螺环舒坦。上述产物的选择性形成是基于可变的反应活性、分子内正环化或脱芳基同环化,并以底物 N-芳基上的取代基为指导。正环化反应由亲电子介导,而异环化反应则由自由基促进,从而在苏丹上实现官能化(硒基或碘基)。这种方法的合成潜力体现在对所得产物中存在的官能团的修饰上
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来源期刊
Advanced Synthesis & Catalysis
Advanced Synthesis & Catalysis 化学-应用化学
CiteScore
9.40
自引率
7.40%
发文量
447
审稿时长
1.8 months
期刊介绍: Advanced Synthesis & Catalysis (ASC) is the leading primary journal in organic, organometallic, and applied chemistry. The high impact of ASC can be attributed to the unique focus of the journal, which publishes exciting new results from academic and industrial labs on efficient, practical, and environmentally friendly organic synthesis. While homogeneous, heterogeneous, organic, and enzyme catalysis are key technologies to achieve green synthesis, significant contributions to the same goal by synthesis design, reaction techniques, flow chemistry, and continuous processing, multiphase catalysis, green solvents, catalyst immobilization, and recycling, separation science, and process development are also featured in ASC. The Aims and Scope can be found in the Notice to Authors or on the first page of the table of contents in every issue.
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