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2000
Volume 29, Issue 15
  • ISSN: 1385-2728
  • E-ISSN: 1875-5348

Abstract

The review describes the oxidative addition of sulfonamides to allylic derivatives. The direction of the sulfonamidation reaction depends on various factors, such as the type of allylic substrate, solvent, oxidant, and the reactivity of the sulfonamide. Intramolecular cyclization of allyl sulfonamides is a simple method for obtaining nitrogen-containing heterocyclic compounds with diverse structures. Reactions between O-allylic substrates and sulfonamides in the presence of oxidizing agents can produce cyclic or linear amino ethers, which are valuable for the synthesis of heterocyclic biologically active compounds. -allylic substances are excellent starting materials for the synthesis of -heterocyclic compounds and linear products with two or three amino groups, providing ample opportunities for further functionalization. When allylsilanes are exposed to oxidizing conditions, they undergo desilylation, allowing for the introduction of an allylic group into reactions with sulfonamides, resulting in products free from Si-heteroatoms, based on a C3-allylic scaffold and sulfonamide nitrogen. The choice of reaction medium and oxidizing agent can significantly affect the course of the reaction, leading to the formation of different products. The main products include aziridines, pyrrolidines, piperazines, lactams, oxazolidines, amino ethers, amidines (imidazoline precursors), and products of aminohalogenetation. This review provides a comparative analysis of the reactivity of sulfonamides in oxidative addition reactions and considers the advantages and disadvantages of synthetic methods.

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/content/journals/coc/10.2174/0113852728348072250113115434
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Synthesis of N-Heterocycles and Linear Adducts from Allyl-Containing Substrates and Sulfonamides
Current Organic Chemistry 29, 1145 (2025); https://doi.org/10.2174/0113852728348072250113115434
/content/journals/coc/10.2174/0113852728348072250113115434
/content/journals/coc/10.2174/0113852728348072250113115434
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  • Article Type:     Review Article
Keyword(s): Allyl compounds; desilylation; heterocyclization; oxidation; solvent interception; sulfonamide

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