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Communication | Regular issue | Vol 55, No. 2, 2001, pp.243-248
Published online, 1st January, 1970
DOI: 10.3987/COM-00-9121
Cycloaddition of Synthetic Equivalent of Non-stabilized Aminonitrile Ylides: A New Route to Amino-substituted Δ2-Imidazolines and Δ3-1,2,4-Triazolines

Otohiko Tsuge,* Taizo Hatta, Hideki Tashiro, and Hironori Maeda

*Department of Applied Chemistry, Sojo University, 4-22-1, Ikeda, Kumamoto-shi, 860-0082, Japan


The N-unsubstituted nonstabilized azomethine ylides generated from the desilylation of N-[(trimethylsilyl)methyl]iminium triflates undergo successful cycloaddition to strongly polarized sulfonylimines and diethyl azodicarboxylate to produce the corresponding Δ2-imidazolines and Δ3-1,2,4-triazolines together with the initial cycloadducts. The initial cycloadducts are converted to the corresponding aminonitrile ylide cycloadducts. Thus the present process provides a new route to amino-substituted Δ2-imidazolines and Δ3-1,2,4-triazolines that are otherwise relatively inaccessible.