American Chemical Society
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Synthesis and X-ray Analysis of an Unprecedented and Stable 2-Aza-4,4-spirocyclopropacyclohexadienone

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journal contribution
posted on 2003-06-17, 00:00 authored by Jay P. Parrish, David B. Kastrinsky, Dale L. Boger
An efficient eight-step synthesis (54% overall) and the subsequent X-ray characterization of 1,2,9,9a-tetrahydrocyclopropa[c]benz[e]-3-azaindol-4-one (CBA) containing an aza variant of the CC-1065/duocarmycin alkylation subunit are detailed. Despite the unique deep-seated aza modification providing an unprecedented and stable 2-aza-4,4-spirocyclopropacyclohexadienone, CBA proved to be structurally identical with CBI, the carbon analogue, in terms of the stereoelectronic alignment of the key cyclopropane, its bond lengths, and the length of the diagnostic C3a−N2 bond reflecting the extent of vinylogous amide conjugation.