New way to cyclic nitrones by cyclization of allenyloximes

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Authors

MAN Stanislav BUCHLOVIČ Marian POTÁČEK Milan

Year of publication 2007
Type Article in Proceedings
Conference Book of Abstracts - XII. Blue Danube Symposium on Heteroyclic Chemistry
MU Faculty or unit

Faculty of Science

Citation
Field Organic chemistry
Keywords allenyloximes; cyclic nitrones; cycloaddition reactions
Description Now we have found a new cyclization reaction of beta-allenyloxime (2) under mild conditions in boiling methanol leading to new five-membered heterocycles (3,4) [5]. When oxime (2) was treated with NaOH in methanol a new nitrone (3) was formed in 77% yield. On the other hand in the mixture of NaOH and NaBH4 in methanol pyrrolidine (4) was obtained in 66% yield. The same product (4) was also obtained from nitrone (3) when treated in the presence of NaOH with NaBH4. structure of both products was unambiguously confirmed by X-Ray analysis of their picrates. The structure and activity of nitrone (3) was proved by its reactivity with dipolarophiles (PhNCO, dimethyl acetylenedicarboxylate).
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