Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 358, Issue 12, Pages 1989-1999Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201600107
Keywords
allene; aza-Prins cyclization; benzo[f]isoquinoline; cascade; iron(III) chloride
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Funding
- National Natural Science Foundation of China [21232006]
- National Basic Research Program [2015CB856600]
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An efficient approach for the synthesis of 1,2,3,4,5,6-hexahydrobenzo[f]isoquinolines viaa tandem aza-Prins/Friedel-Crafts cyclization from 2-arylethyl-2,3-butadienyl tosylamides and aldehydes has been developed. This iron(III) chloride-catalyzed cascade cyclization at the room temperature with different types of aldehydes, such as aromatic and heteroaromatic aldehydes, alkyl aldehydes, and ,-unsaturated aldehydes, affords the products in moderate to excellent yields (up to 97%). In this reaction, chlorotrimethylsilane was applied to activate the aldehydes. The cheap catalyst, the mild reaction conditions, and the broad scope of the substrates make this method highly useful.
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