Reactions of 1,3-dipolar aldazines and ketazines with the dipolarophile dimethyl acetylenedicarboxylate
2002; NRC Research Press; Volume: 80; Issue: 10 Linguagem: Inglês
10.1139/v02-169
ISSN1480-3291
AutoresAbdullah El‐Alali, Ahmed S.N. Al-Kamali,
Tópico(s)Synthesis and Reactivity of Heterocycles
ResumoThe prepared aldazines (aldehyde azines) and ketazines (ketone azines) were allowed to react with 2 mol of the acetylene derivative. The first products formed were pentalene azine derivatives, which in some cases underwent skeletal rearrangment into acyclic tetraene azines. The latter underwent, in the case of some aldazine products, further skeletal rearrangment into N-allyl pyrazoles. The occurence of these rearrangments is dependant on the nature of the aldehydes or ketones used.Key words: dimethyl acetylenedicarboxylate (DMAD), aldazines, ketazines, N-allyl pyrazoles.
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