[3+3] Cycloadditions of Azomethine Ylides with Nitrile Imines for the Synthesis of 2,3,4,5‐Tetrahydro‐1,2,4‐Triazine‐5‐Carboxylates

An unprecedented and efficient [3+3] cycloaddition of azomethine ylides with nitrile imines has been achieved. A series of 2,3,4,5‐tetrahydro‐1,2,4‐triazine‐5‐carboxylates were obtained in moderate to excellent yields. Notable features of this reaction include readily accessible reagents, broad subs...

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Bibliographic Details
Published in:European journal of organic chemistry 2022-09, Vol.2022 (35), p.n/a
Main Authors: Gao, Limei M., Wang, Xiaomeng M., Wei, Qinglang L., Su, Kexin X., Huang, Renhong H., Guo, Ju, Zheng, Yongsheng S., Liu, Jikai K.
Format: Article
Language:English
Subjects:
1,2,4-Trazine
[3+3] Cycloaddition
Azomethine ylide
Carboxylates
Cycloaddition
Imines
Nitrile imine
Reagents
Substrates
Unnatural amino acid
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Summary:An unprecedented and efficient [3+3] cycloaddition of azomethine ylides with nitrile imines has been achieved. A series of 2,3,4,5‐tetrahydro‐1,2,4‐triazine‐5‐carboxylates were obtained in moderate to excellent yields. Notable features of this reaction include readily accessible reagents, broad substrate scope (34 examples), mild reaction conditions and operational simplicity. [3+3] cycloaddition of azomethine ylides with nitrile imines was established to access unnatural cyclic amino acids containing 1,2,4‐triazines. A series of 2,3,4,5‐tetrahydro‐1,2,4‐triazine‐5‐carboxylates were obtained in moderate to excellent yields under mild reaction conditions.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202200768