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
supporting information
p. 18478 - 18483
(2021/07/19)
Reaction of 2-allyloxy(thio)-4-methylquinolines with halogens
It was established that the halogenation of 2-allyloxy(thio)-4-methylquinolines leads to the formation of 3-halogenomethyl-2,3-dihydrooxazolo(thiazolo)[3,2-a]quinolinium halides. 1997 Plenum Publishing Corporation.
Kim,Sashin,Kozlovskaya,Andreeva
p. 1075 - 1077
(2007/10/03)
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