Free radical carbochloromethylations
of ortho-cyanoarylacrylamides and N-(arylsulfonyl)acrylamides
have been developed by employing simple alkyl chlorides as the chloromethyl
source. The transformations are characterized by wide functional group
compatibility and utilizing readily available reagents, thus providing
efficient methods for constructing polychloromethyl-substituted quinoline-2,4-diones
and α-aryl-β-polychloromethylated amides.
A radical bicyclization of 2-cyanoaryl acrylamides with dicumyl peroxide has been developed for constructing a broad spectrum of benzo[h]naphtho [1,8-bc][1,6]naphthyridine. This reaction allows the formation of three new chemical bonds through addition of methyl radical across alkene double bond, intramolecular addition of carbon-centered radical to cyano group and cyclization of the iminyl radical cascade, and features simple reaction system and wide substrate scope.
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