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This protocol was applied to a series of <jats:italic>N<\/jats:italic>\u2010(alkoxycarbonyl)\u20102\u2010alkynylindoles containing different substituents. The reaction conditions also tolerated a variety of diorganyl diselenides having both electron donating and electron withdrawing groups. However, the reaction did not work for diorganyl disulfides and ditellurides. The reaction mechanism seems to proceed via an ionic pathway and the cooperative action between iron(III) chloride and diorganyl diselenides is crucial for successful cyclization. We also found that using the same starting materials, by simply changing the electrophilic source to iodine, led to the formation of 4\u2010iodo\u2010oxazinoindolones. The high reactivity of Csp<jats:sup>2<\/jats:sup>\u2212Se and Csp<jats:sup>2<\/jats:sup>\u2212I bonds were tested under cross\u2010coupling conditions leading to the preparation of a new class of functionalized indole derivatives. In addition, the absorption, emission and electrochemical properties of 4\u2010organoselanyl oxazinoindolones showed an important relationship with the substituents of the aromatic rings. The advantages of the methodology include the use of electrophilic to promote the cyclization reaction and functionalization of the indole ring, and the electronic properties presented by the prepared compounds can be exploited as probes, analyte detectors and optical materials.<\/jats:p>","DOI":"10.1002\/chem.202202847","type":"journal-article","created":{"date-parts":[[2022,11,2]],"date-time":"2022-11-02T11:15:03Z","timestamp":1667387703000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":6,"title":["Electrophile\u2010Promoted Nucleophilic Cyclization of 2\u2010Alkynylindoles to Give 4\u2010Substituted Oxazinoindolones"],"prefix":"10.1002","volume":"29","author":[{"given":"Guilherme","family":"Leonel","sequence":"first","affiliation":[{"name":"Laborat\u00f3rio de S\u00edntese, Reatividade, Avalia\u00e7\u00e3o Farmacol\u00f3gica Toxicol\u00f3gica de Organocalcog\u00eanios, CCNE, UFSM  Santa Maria Rio Grande do Sul 97105-900 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