The remarkable reactivity of 2-alkylidene-imidazolidines in inverse diels-alder reactions
β Scribed by Ursula Gruseck; Manfred Heuschmann
- Publisher
- Elsevier Science
- Year
- 1987
- Tongue
- French
- Weight
- 229 KB
- Volume
- 28
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
The reactivity of 2-alkylidene-imidazolidines 2 in inverse Diels-Alder syntheses with several pyridazines and 1,2,4-triazines is compared with that of acyclic ketene acetals 1. The 2-cyclopropylidene-imidazolidine 2~ is particularly suited for less reactive dienes.
Extensive work of Sauer 1) and others2) has shown that ketene N,N-acetals Ia,
π SIMILAR VOLUMES
The structure of the a-chloronitroso ether I, obtained from the hydroximolactone 2 and tert-butyl hypochlorite (89 %), was established by X-ray crystallographic analysis. The [4 + 2 1 cycloadditions of 1 with the dienes 3 and %I1 led to the N-unsubstituted 3,6-dihydro-2H-1,2-oxazines 6 and 12-16 in
Intermolecular cycloadditions between trialkyl 1,2,4-triazine-4,5,6-tricarboxyIatesand protected2-aminoimidazolegave IH-imidazo[4,5-c]pyridines (3-deazapurines)andthe rearranged3Hpyrido[3,2-d]pyrimid-4-ones (8-deazapteridines). No cycloadditions wereobservedwithimidazoleand2phenylimidazole.Q 1997Els