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Synthesis of Seleno‐Heterocycles via Electrophilic/Radical Cyclization of Alkyne Containing Heteroatoms
Advanced Synthesis & Catalysis ( IF 5.4 ) Pub Date : 2020-06-21 , DOI: 10.1002/adsc.202000490
Amol D. Sonawane 1 , Rohini A. Sonawane 1 , Masayuki Ninomiya 1 , Mamoru Koketsu 1
Affiliation  

containing heterocyclic scaffolds by virtue of their interesting reactivities and a broad range of applications in the medicinal and materials chemistry. This review involves the electrophilic/radical cyclization of alkynes containing heteroatoms which resulted into the novel Se‐heterocycles. The synthesis of seleno‐heterocycles via different nucleophiles including O, N, S, Se, Te, and C‐nucleophiles is exhaustively discussed. Also, one‐pot electrophilic cyclization of 1,3‐diynes and 1,3,5‐triynes was described in details. Furthermore, the various mechanisms underlying the synthesis of selenium‐β‐lactam, carbapenem heterocycle, bis‐ and tris‐selenide alkene, β‐selenosulfonation and selenated alkynes were discussed. The Se‐heterocycles reported in this review allow preparing these selenated compounds bearing the selenium moiety both on the rings (outside) and inside the ring (e. g. selenophenes). The review demonstrates the growing opportunities to construct selenium containing heterocycles from alkynes containing heteroatoms.

中文翻译:

通过含杂原子的炔烃的亲电/自由基环合反应合成硒代杂环

由于它们具有有趣的反应性以及在药物和材料化学中的广泛应用,因此含有杂环骨架。这篇综述涉及含有杂原子的炔烃的亲电/自由基环化反应,从而形成了新颖的Se-杂环。通过不同的亲核试剂(包括ONSSeTeC-)合成硒杂环亲核试剂已被详尽讨论。此外,还详细描述了1,3-二炔和1,3,5-三炔的一锅亲电环化反应。此外,还讨论了硒-β-内酰胺,碳青霉烯杂环,双-和三-硒化烯烃,β-硒磺化和硒代炔烃合成的各种机理。在该综述中报道的硒杂环化合物允许制备在环(外部)和环内部(例如硒烯)都带有硒部分的这些硒化的化合物。该综述证明了从含有杂原子的炔烃中构建含硒杂环的机会越来越大。
更新日期:2020-06-21
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