Cycloisomerization of Carbamoyl Chlorides in Hexafluoroisopropanol: Stereoselective Synthesis of Chlorinated Methylene Oxindoles and Quinolinones
Hexafluoroisopropanol (HFIP) was employed as an additive for the generation of 3-(chloromethylene)oxindoles via the chloroacylation of alkyne-tethered carbamoyl chlorides. This reaction avoids the use of a metal catalyst and accesses products in high yields and stereoselectivities. Additionally, this reaction is scalable and proved amenable to a series of product derivatizations, including the synthesis of nintedanib. The reactivity of alkene-tethered carbamoyl chlorides with hexafluoroisopropanol (HFIP) was harnessed towards the synthesis of 2-quinolinones.
Bajohr, Jonathan,Lautens, Mark,Mirabi, Bijan,Rodríguez, José F.,Whyte, Andrew,Zhang, Anji
Copper-catalyzed regiospecific synthesis of N-alkylbenzimidazoles
(Chemical Equation Presented) A copper-catalyzed method is described for the preparation of N-alkylbenzimidazoles in regioisomerically pure form starting from o-haloanilines. The method utilizing CuI and trans-N,N′-dimethyl-1, 2-cyclohexanediamine allows the preparation of N-alkylbenzimidazoles in good to excellent yields.
Zheng, Nan,Buchwald, Stephen L.
p. 4749 - 4751
(2008/03/14)
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