Cycloaddition reactions of 2,3-dihydro-1H-1,4-diazepines with nitrile oxides and imines. Synthesis of bis[1,2,4]oxadiazolo-and bis[1,2,4]triazolo[1,4]diazepine derivatives

Autor:	Maria C. Aversa, Paola Bonaccorsi, Placido Giannetto, David A. Leigh
Rok vydání:	2009
Předmět:	chemistry.chemical_classification Double bond Nitrile Nitrilimine Stereochemistry Organic Chemistry Imine Medicinal chemistry Cycloaddition chemistry.chemical_compound Diazepine chemistry Ylide 1 3-Dipolar cycloaddition
Zdroj:	Journal of Heterocyclic Chemistry. 26:1619-1622
ISSN:	1943-5193 0022-152X
DOI:	10.1002/jhet.5570260620
Popis:	New heterotricyclic systems, 6,10a,11,11a-tetrahydro-5H-bis[1,2,4]oxadiazolo[4,5-d:5′,4′-g][1,4]diazepines 6,7,9-11 and 5,6,10,10a,11,11a-hexahydro-1H-bis[1,2,4]triazolo[4,3-d:3′,4′-g][1,4]diazepines 8,12 have been obtained by double site- and regie-specific 1,3-dipolar cycloaddition of mesitylnitrile oxide (1) or diphenylnitrile imine (2) to 5,7-disubstituted 2,3-dihydro-1H-1,4-diazepines 3-5. The structure of the synthesized bis-adducts 6-12 shows that the hetero double bonds are much more reactive than the olefinic ones in the dipolarophiles under study. No evidence for the formation of mono-adducts was obtained.
Databáze:	OpenAIRE
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