Polyfunctionalized cage compounds by pericyclic domino processes of 4,5- dicyanopyridazine with dienes: Applications and limits

Journal of Organic Chemistry

Volumn 65, Issue 2, 2000, Pages 360-364

  Giomi, Donatella ^a   Nesi, Rodolfo ^a   Turchi, Stefania ^a   Mura, Elena ^a  

^a UNIVERSITY OF FLORENCE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; PYRIDAZINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; ITALY; MOLECULAR INTERACTION; ORGANIC CHEMISTRY; SYNTHESIS;

EID: 0034723237     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991191v     Document Type: Article

References (17)

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11. For the greater reactivity of the bis-allyl amide moiety with respect to the corresponding ester in intramolecular Diels-Alder reactions, see: Swarbrick, T. M.; Markó, I. E.; Kennard, L. Tetrahedron Lett. 1991, 32, 2549.
12. Impressive diastereospecificity was observed for intramolecular cycloadditions of cyclohexa-1,3-diene derivatives as a consequence of a more pronounced methyl/methyl overcrowding: Näf, F.; Decorzant, R.; Giersch, W.; Ohloff, G. Helv. Chim. Acta 1981, 64, 1387.
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16. The values in square brackets refer to the minor diastereomer.
17. When a total conversion of 19 was attained under more forcing conditions, the desired compound 20 was isolated in much lower yield from the more complex reaction mixture.