TfOH-catalyzed formal [3+2] cycloaddition of N-tosylaziridine dicarboxylates and nitriles: Synthesis of tetrafunctionalized 2-imidazolines

[Display omitted] •TfOH-catalyzed cycloaddition of N-tosylaziridine dicarboxylates and nitriles gave tetrafunctionalized 2-imidazolines.•The method features mild conditions and wide scope of substrates.•First example of C–N bond cleavage of N-tosylaziridine dicarboxylates catalyzed by Brønsted acid....

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Bibliographic Details
Published in:Tetrahedron letters 2020-03, Vol.61 (10), p.151576, Article 151576
Main Authors: Zuo, Qinglu, Shi, Zhichao, Zhan, Feng, Wang, Zhe, Lin, Jin-Shun, Jiang, Yuyang
Format: Article
Language:English
Subjects:
N-Tosylaziridine dicarboxylates
Nitrile
Tetrafunctionalized 2-imidazoline
TfOH
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Summary:[Display omitted] •TfOH-catalyzed cycloaddition of N-tosylaziridine dicarboxylates and nitriles gave tetrafunctionalized 2-imidazolines.•The method features mild conditions and wide scope of substrates.•First example of C–N bond cleavage of N-tosylaziridine dicarboxylates catalyzed by Brønsted acid.•A SN2 process. We developed an efficient method for synthesis of tetrafunctionalized 2-imidazolines using TfOH-catalyzed formal [3+2] cycloaddition of N-tosylaziridine dicarboxylates and nitriles. This is the first report of C–N bond cleavage of N-tosylaziridine dicarboxylates catalyzed by Brønsted acid and the reaction worked well over wide scope of substrates in good to excellent yields under mild conditions. The method has the potential to be applied to pharmaceutical design and synthesis of tetrafunctionalized 2-imidazolines.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2019.151576