Journal of the Chemical Society. Perkin transactions I p. 2523 - 2529 (1996)
Update date:2022-08-16
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Malamidou-Xenikaki, Elizabeth
Cyclooctane-1,5-dione 1 undergoes transannular cyclization upon treatment with 1,2-diaminoarenes 2a-d or 1,3-diaminopropane 5a to afford the 2,5-diazatricyclo[4.3.3.01,5]dodecan-6-ols 3a-d or 2,6-diazatricyclo[5.3.3.01,6]tridecan-7-ol 6 respectively, in moderate to good yields. The ethoxycarbonylmethyldiazatricyclo analogues 22a,b result from a similar reaction of 5-ethoxycarbonylmethylenecyclooctanone 19 with diaminoalkanes 5a,b. Acetylation of tricyclo compound 3d leads, among others, to the unexpected product 2-diacetylmethylidene-1-(5-oxocyclooct-1-en-1-yl)-3-methyl-2,3- dihydrobenzimidazole 12.
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