A1 Journal article (refereed)
Synthesis of Polycyclic Indolines utilizing a reduction/cyclization cascade reaction (2021)

Zhang, J., Xia, W., Qu, M., Huda, S., Ward, J., Rissanen, K., & Albrecht, M. (2021). Synthesis of Polycyclic Indolines utilizing a reduction/cyclization cascade reaction. European Journal of Organic Chemistry, 2021(45), 6097-6101. https://doi.org/10.1002/ejoc.202101191

JYU authors or editors

Publication details

All authors or editors: Zhang, Jingyu; Xia, Wei; Qu, Meilin; Huda, Saskia; Ward, Jas; Rissanen, Kari; Albrecht, Markus

Journal or series: European Journal of Organic Chemistry

ISSN: 1434-193X

eISSN: 1099-0690

Publication year: 2021

Publication date: 07/10/2021

Volume: 2021

Issue number: 45

Pages range: 6097-6101

Publisher: Wiley-VCH Verlag

Publication country: Germany

Publication language: English

DOI: https://doi.org/10.1002/ejoc.202101191

Publication open access: Openly available

Publication channel open access: Partially open access channel

Publication is parallel published (JYX): https://jyx.jyu.fi/handle/123456789/82557

Abstract

Subsequent reduction and dearomatizing cyclization reactions open up an entry into the synthesis of novel N-fused polycyclic indolines. The dearomatizing cyclization as key step of the sequence proceeds well with Cu(OTf)2 or TfOH as catalyst. At elevated temperature reduction of nitro-substituted precursors with iron under acidic conditions affords a broad variety of polycyclic indolines directly in a two-step cascade reaction in good to excellent yields. Using the developed protocol, the alkaloids Tryptanthrin and Phaitanthrin C have been prepared.

Keywords: organic compounds; chemical synthesis; oxidation-reduction reaction; catalysis

Free keywords: acid catalysis; cyclization; cascade reactions; dearomatization; nitrogen heterocycles

Contributing organizations

Ministry reporting: Yes

Reporting Year: 2022

JUFO rating: 1