Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 359, Issue 9, Pages 1552-1562Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201601327
Keywords
cascade annulation; 2-nitrocinnamaldehydes; nitrogen heterocycles; synthetic methods; -tetralones
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Funding
- Nano Material Technology Development Program of the Korean National Research Foundation (NRF) - Korean Ministry of Education, Science, and Technology [2012M3A7B4049675]
- National Research Foundation of Korea (NRF) - Korea government (MSIP) [NRF-2014R1A2A1A11052391]
- Priority Research Centers Program [2014R1A6A1031189]
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This paper describes the transition metal-free indole annulation-oxidative cross-coupling of 2-nitrocinnamaldehydes or (E)-3-(1-nitronaphthalen-2-yl)acrylaldehyde with -tetralones for the construction of diverse 3-naphthylindole and 3-naphthylbenzo[g]indole fluorophores in moderate to good yields. This unique annulation reaction proceeds via the domino Michael addition/hemiacetalization/intramolecular addition of an enolate to a nitro group/decarbonylation/oxidative aromatization sequence under transition metal-free conditions without the use of an external reductant and oxidant. The synthetic utility of this protocol has been also demonstrated by evaluating the photophysical properties of the synthesized 3-naphthylindole and 3-naphthylbenzo[g]indole derivatives.
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