Synthesis and Some Reactions of Functionalized Benzo[b]azonines and Bi(benzo[b]azonines)
نویسندگان
چکیده
Tetrahydro-1H-benzo[b]azonin-2,7-dione (2a) has been used as a precursor in the synthesis of dibenzo[b,f ][1,5]diazacyclododecene and dibenzo[b,g][1,6]diazacyclododecene ring systems 4 and 5, respectively, via periodate oxidation of the appropriate indolo-benzo[b]azonines 3 and 7. The synthesis of hexahydro-benzo[b][1,4]diazecin-2,7-dione (10) has been achieved by the Schmidt reaction of 2a. The periodate oxidation of 9,9′-methylenebis(2,3,4,9-tetrahydro-1H-carbazole) (11) afforded 1,1′methylenebis(3,4,5,6-tetrahydro-1H-benzo[b]azonin-2,7-dione) (12). Its 6,6′-methylenebis isomer 13 was obtained by treating 2a with formaldehyde. Oxidation of 16 gave the unsymmetrical bi(benzo [b]azonine) 17. The Mannich reaction of 2a led to a mixture of its 6-methylene derivative 19 and the spirocyclic system 20. The reactions of 2a with aldimines and aromatic aldehydes were also investigated.
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