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Title: Alkanethiol-Mediated Cyclization of o-Alkynylisocyanobenzenes: Synthesis of Bis-Thiolated Indole Derivatives
Authors: Kannika La-Ongthong
Phiphop Naweephattana
Onnicha Khaikate
Panida Surawatanawong
Darunee Soorukram
Manat Pohmakotr
Vichai Reutrakul
Pawaret Leowanawat
Chutima Kuhakarn
Mahidol University
Keywords: Chemistry
Issue Date: 15-May-2020
Citation: Journal of Organic Chemistry. Vol.85, No.10 (2020), 6338-6351
Abstract: Copyright © 2020 American Chemical Society. Reactions of o-alkynylisocyanobenzenes with a variety of alkanethiols (Alk-SH) provide the corresponding bis-thiolated indole derivatives. The advantages of the reaction include metal-free, room-temperature, mild reaction conditions and broad functional group compatibility. The reaction proceeds via nucleophilic addition of an alkanethiol to an isonitrile moiety, 5-exo cyclization, followed by nucleophilic addition of an alkanethiol to a 3-alkylidene indole intermediate. Density functional calculations on the electronic structures and relative free energies of 5-exo and 6-endo cyclization pathways support that the 5-exo cyclization is preferable.
ISSN: 15206904
Appears in Collections:Scopus 2020

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