Publication: Alkanethiol-Mediated Cyclization of o-Alkynylisocyanobenzenes: Synthesis of Bis-Thiolated Indole Derivatives
Issued Date
2020-05-15
Resource Type
ISSN
15206904
00223263
00223263
Other identifier(s)
2-s2.0-85087946538
Rights
Mahidol University
Rights Holder(s)
SCOPUS
Bibliographic Citation
Journal of Organic Chemistry. Vol.85, No.10 (2020), 6338-6351
Suggested Citation
Kannika La-Ongthong, Phiphop Naweephattana, Onnicha Khaikate, Panida Surawatanawong, Darunee Soorukram, Manat Pohmakotr, Vichai Reutrakul, Pawaret Leowanawat, Chutima Kuhakarn Alkanethiol-Mediated Cyclization of o-Alkynylisocyanobenzenes: Synthesis of Bis-Thiolated Indole Derivatives. Journal of Organic Chemistry. Vol.85, No.10 (2020), 6338-6351. doi:10.1021/acs.joc.0c00003 Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/57811
Research Projects
Organizational Units
Authors
Journal Issue
Thesis
Title
Alkanethiol-Mediated Cyclization of o-Alkynylisocyanobenzenes: Synthesis of Bis-Thiolated Indole Derivatives
Other Contributor(s)
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.