Abstract
The reaction of 2-fluoroalkyl-1-iodoethylenes with arylamines ( 1 ) and the subsequent acid promoted transformation of the products were described. In the presence of ZnCl 2 and triethylamine, 1 reacted readily with various p-substituted anilines in HMPA under a vacuum of 60–70 mmHg to give the corresponding enaminoaldehydes ( 2 ) as a mixture of E- and Z-isomers. Cyclization of 2 , without further purification in refluxing toluene, catalyzed by strong acids such as p-toluene sulfonic acid and trifluoromethanesulfonic acid gave 2-fluoroalkylquinolines ( 3 ) in good yields, while fluoroalkylated enaminoketones ( 4 ) were obtained predominantly when 2 was treated with acids in aqueous THF solution. A possible mechanism was proposed for the formation of 3 and 4 .
Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
