Publication: Synthesis of Indolo-and Benzothieno[2,3-b]quinolines by a Cascade Cyclization of o-Alkynylisocyanobenzene Derivatives
Issued Date
2019-01-01
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ISSN
15206904
00223263
00223263
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2-s2.0-85075579753
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Mahidol University
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SCOPUS
Bibliographic Citation
Journal of Organic Chemistry. (2019)
Suggested Citation
Onnicha Khaikate, Natthamon Inthalaeng, Jatuporn Meesin, Kritchasorn Kantarod, Manat Pohmakotr, Vichai Reutrakul, Darunee Soorukram, Pawaret Leowanawat, Chutima Kuhakarn Synthesis of Indolo-and Benzothieno[2,3-b]quinolines by a Cascade Cyclization of o-Alkynylisocyanobenzene Derivatives. Journal of Organic Chemistry. (2019). doi:10.1021/acs.joc.9b02081 Retrieved from: https://repository.li.mahidol.ac.th/handle/123456789/50581
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Title
Synthesis of Indolo-and Benzothieno[2,3-b]quinolines by a Cascade Cyclization of o-Alkynylisocyanobenzene Derivatives
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Abstract
© 2019 American Chemical Society. A new synthetic approach for the synthesis of indolo[2,3-b]quinolines and benzothieno[2,3-b]quinolines has been developed by employing the freshly prepared o-alkynylisocyanobenzenes derived from o-alkynylformamide derivatives as substrates. The synthetic transformations involved chloride-ion-triggered 6-endo cyclization of o-alkynylisocyanobenzenes to generate 2-chloroquinolines in situ, which further cyclized intramolecularly with nitrogen or sulfur atom via a cascade process to provide the corresponding indolo[2,3-b]quinolines and benzothieno[2,3-b]quinolines, respectively, in moderate to excellent yields.