ABSTRACT
An azido-radical-triggered cyclization of N-(o-cyanobiaryl)acrylamides with TMSN3via a C(sp3)-N/C(sp2)-C(sp3)/C(sp2)-N bond formation cascade is described. This reaction features mild conditions and high bond-forming efficiency, making it an efficient method for the construction of azide-substituted pyridophenanthridines.
ABSTRACT
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-ß-polychloromethylated amides.
ABSTRACT
Radical cascade cyclizations of N-cyanamide alkenes have been developed for the divergent synthesis of pyrroloquinazolinones bearing azido, alkenyl, and nitro groups by controlling the reaction conditions. The reaction temperature and the loading of the base play important roles in the different reaction pathways. These reactions are characterized by wide functional group compatibility and mild conditions.
ABSTRACT
An oxidative azido-difluoromethylthiolation of alkenes by employing TMSN3 as the azide source and PhSO2SCF2H as the difluoromethylthiolation reagent is reported. The present method is characterized by good functional group tolerance, broad substrate scope, and short reaction time, thereby providing an efficient access to synthetically useful ß-difluoromethylthiolated azides. Mechanistic studies indicate a radical pathway involved in the reaction.
Subject(s)
Alkenes , Azides , Alkenes/chemistry , Azides/chemistry , Catalysis , Indicators and ReagentsABSTRACT
A visible-light-promoted cascade cyclization of 3-ethynyl-[1,1'-biphenyl]-2-carbonitriles with unsaturated α-bromocarbonyls for the synthesis of tetrahydrobenzo[mn]cyclopenta[b]acridines is described. Three C(sp3)-C(sp2) bonds, one C(sp2)-N bond, and three cycles can be formed in a single reaction through the addition of a C-centered radical to the carbon-carbon triple bond and three radical cyclizations. This reaction features mild conditions, wide substrate scope, and high bond-forming efficiency.