Cycloisomerization of Carbamoyl Chlorides in Hexafluoroisopropanol: Stereoselective Synthesis of Chlorinated Methylene Oxindoles and Quinolinones

Autor:	Bijan Mirabi, Andrew Whyte, Anji Zhang, Mark Lautens, José F. Rodríguez, Jonathan Bajohr
Rok vydání:	2021
Předmět:	010405 organic chemistry General Medicine General Chemistry 010402 general chemistry 01 natural sciences Combinatorial chemistry Catalysis 0104 chemical sciences chemistry.chemical_compound Cycloisomerization chemistry Stereoselectivity Reactivity (chemistry) Methylene
Zdroj:	Angewandte Chemie International Edition. 60:18478-18483
ISSN:	1521-3773 1433-7851
DOI:	10.1002/anie.202103323
Popis:	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.
Databáze:	OpenAIRE
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