Meisenheimer rearrangement of azetopyridoindoles. Part 4. Ring expansion of 2-vinyl-1,2,4,5,10,10b-hexahydroazeto[1′,2′:1,2]pyrido[3,4-b]indole N-oxides

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Abstract
Oxidation of 1,2-cis-1,2,4,5,10, 10b-hexahydroazeto[1′,2′:1,2]pyrido[3,4-b]indole-1-carboxylate derivatives 1a–d and 5 with m-chloroperbenzoic acid in methylene dichloride gave hexahydro[1′,2′]oxazepino[2′,3′:1,2]pyrido[3,4-b]indole-l-carboxylates 2a-d and 6, which have a 12-carbaeudistomin skeleton, via the [2,3]-Meisenheimer rearrangement of the N-oxides. On the other hand, peracid oxidation of the corresponding 1,2-trans derivative 7 gave the hexahydroisoxazolo[2′,3′:1,2]pyrido[3,4-b]indole 8via the [1,2]-Meisenheimer rearrangement of the corresponding N-oxide. Stereoscopic X-ray molecular structures for (13-methyl-1,4,7,8,13,13-bhexahydro[1′,2′]oxazepino[2′,3′:1,2]pyrido[3,4-b]indol-1-yl)methanol 3 and (11-methyl-2-vinyl-1,2,5,6,11,11b-hexahydro isoxazolo[2′,3′:1,2]pyrido[3,4-b]indol-1-yl)methanol 12 are presented.

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