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Electrophilic Thiocyanation of Tryptamine Derivatives: Divergent Synthesis of SCN-Containing Indole Compounds. 2022

Ai-Hui Ye, and Xu-Feng Song, and Zhi-Min Chen
School of Chemistry and Chemical Engineering, Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, Shanghai Jiao Tong University, Shanghai, 200240, P. R. China.

A tandem dearomative electrophilic thiocyanation/cyclization/acylation of indoles was developed for the first time, which is enabled by acyl chloride. A variety of 3-SCN pyrroloindolines were obtained with moderate to excellent yields. Interestingly, following replacement of acyl chloride with methanesulfonic acid, 2-SCN tryptamines were obtained using the same starting substrates and reagents. Furthermore, catalytic enantioselective manner of thiocyanation/cyclization/acylation reaction was also studied. An enantiomer self-disproportionation effect of 3-SCN pyrroloindolines was discovered. A series of chiral 3-SCN pyrroloindolines were obtained with high enantioselectivities.

UI MeSH Term Description Entries
D007211 Indoles Benzopyrroles with the nitrogen at the number one carbon adjacent to the benzyl portion, in contrast to ISOINDOLES which have the nitrogen away from the six-membered ring.
D011758 Pyrroles Azoles of one NITROGEN and two double bonds that have aromatic chemical properties. Pyrrole
D002712 Chlorides Inorganic compounds derived from hydrochloric acid that contain the Cl- ion. Chloride,Chloride Ion Level,Ion Level, Chloride,Level, Chloride Ion
D014363 Tryptamines Decarboxylated monoamine derivatives of TRYPTOPHAN. Indolylethylamines,Triptan,Triptans

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