Publication: Synthesis of: N -alkyl-3-sulfonylindoles and N -alkyl-3-sulfanylindoles by cascade annulation of 2-alkynyl- N, N -dialkylanilines
Issued Date
2017-01-01
Resource Type
ISSN
14770520
Other identifier(s)
2-s2.0-85021673690
Rights
Mahidol University
Rights Holder(s)
SCOPUS
Bibliographic Citation
Organic and Biomolecular Chemistry. Vol.15, No.17 (2017), 3662-3669
Suggested Citation
Jatuporn Meesin, Manat Pohmakotr, Vichai Reutrakul, Darunee Soorukram, Pawaret Leowanawat, Chutima Kuhakarn Synthesis of: N -alkyl-3-sulfonylindoles and N -alkyl-3-sulfanylindoles by cascade annulation of 2-alkynyl- N, N -dialkylanilines. Organic and Biomolecular Chemistry. Vol.15, No.17 (2017), 3662-3669. doi:10.1039/c7ob00366h Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/42050
Research Projects
Organizational Units
Authors
Journal Issue
Thesis
Title
Synthesis of: N -alkyl-3-sulfonylindoles and N -alkyl-3-sulfanylindoles by cascade annulation of 2-alkynyl- N, N -dialkylanilines
Other Contributor(s)
Abstract
© The Royal Society of Chemistry 2017. An efficient and metal-free approach to N-alkyl-3-sulfonylindoles and N-alkyl-3-sulfanylindoles from 2-alkynyl-N,N-dialkylanilines has been developed. In the presence of iodine and tert-butylhydroperoxide (TBHP), a variety of 2-alkynyl-N,N-dialkylanilines underwent a cascade radical annulation to yield 3-arylsulfonylindoles. In contrast, 3-arylsulfanylindoles were conveniently prepared by iodine mediated electrophilic annulation reactions. The present protocol uses the economical and environmentally friendly I2-TBHP or I2system, and potentially bioactive N-alkyl-3-sulfonylindoles and N-alkyl-3-sulfanylindoles with various functional groups were successfully synthesized in moderate to good yields.