Lauta, Nicholas R.; Williams, Ryan E.; Smith, David T.; Kumirov, Vlad K.; Njardarson, Jon T. published their research in Journal of Organic Chemistry in 2021. The article was titled 《Oxidative Route to Indoles via Intramolecular Amino-Hydroxylation of o-Allenyl Anilines》.Synthetic Route of C6H5ClIN The article contains the following contents:
A new intramol. oxidative amino-hydroxylation of o-allenyl anilines was reported. Treatment of carbamate-protected anilines with lead(IV) carboxylates in dichloromethane at room temperature resulted in facile tandem C-N (allene cyclization) and C-O bond formation (carboxylate trapping) to form indole products I [R1 = H, Br, MeO, etc.; R2 = Me, H2CCCl3, t-Bu, Bn; R3 = Me, Ph, 4-FC6H4, 4-F3CC6H4, 4-MeOC6H4, HC=CHPh; R4 = H, Me; R5 = H, Me] . Detailed reaction scope, mechanistic and kinetic studies suggested a reaction pathway involving an initial Wessely dearomatization step followed by cyclization and rearomatization. In the experiment, the researchers used many compounds, for example, 4-Chloro-2-iodoaniline(cas: 63069-48-7Synthetic Route of C6H5ClIN)
4-Chloro-2-iodoaniline(cas: 63069-48-7) belongs to anime. To avoid the problem of multiple alkylation, methods have been devised for “blocking” substitution so that only one alkyl group is introduced. The Gabriel synthesis is one such method; it utilizes phthalimide, C6H4(CO)2NH, whose one acidic hydrogen atom has been removed upon the addition of a base such as KOH to form a salt.Synthetic Route of C6H5ClIN
Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com