Naphth indole

The naphth[3,2,l-cr/]indole ring system, e.g. 290, was constructed by Miki in very good yield via an intramolecular Heck reaction of triflate 289 [284]. The corresponding bromide furnished 290 in 74% yield. Interestingly, attempted radical cyclization of the bromide with BujSnH failed. 

Miki, Y, Shirokoshi, H., Asai, M. et al. (2003) Synthesis of naphth[3,2,l-Cii]indole by Heck cyclization of 2-methoxycarbonyl-3-benzoylindoles. Heterocycles, 60, 2095-101. 

Scheme 1 The reversible rearrangement of 1,3-dihydro-1,3,3-trimethyl-spiro[2//-indol-2,3 -(3//)-naphth(2,l-Z>Xl,4)oxazin] (Photorom I) triggered by UV irradiation...

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