Publication details
New way to cyclic nitrones by cyclization of allenyloximes
| Authors | |
|---|---|
| Year of publication | 2007 |
| Type | Article in Proceedings |
| Conference | Book of Abstracts - XII. Blue Danube Symposium on Heteroyclic Chemistry |
| MU Faculty or unit | |
| 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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