Reaction of o-Iodoaniline with Aromatic Ketones in DMSO: Synthesis of 2-Aryl or 2-Hetarylindoles

MT Baumgartner, MA Nazareno, MC Murguía…

文献索引：Baumgartner, Maria T.; Nazareno, Monica A.; Murguia, Marcelo C.; Pierini, Adriana B.; Rossi, Roberto A. Synthesis, 1999 , # 12 p. 2053 - 2056

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被引用次数: 14

摘要

Abstract: The reactions of o-iodoaniline (1) with the enolate anions from acetone (2), acetophenone (4), 2-acetylnaphthalene (6), 2-acetyl-1-methylpyrrole (8a) and 2- acetylthiophene (8b) in DMSO give respectively the corresponding 2-substituted indoles in 63, 88, 73, 93 and 82% yields. These reactions are proposed to take place by an SRN1 mechanism. Depending on the ketone enolate ion involved, the reactions can occur under ...