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One‐Pot Synthesis of Furo‐ or Thienoquinolines through Sequential Imination and Intramolecular Palladium‐Catalyzed Direct Arylation
Author(s) -
Beydoun Kassem,
Doucet Henri
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201201142
Subject(s) - chemistry , furan , intramolecular force , palladium , moiety , thiophene , catalysis , medicinal chemistry , organic chemistry , combinatorial chemistry
The sequential imination and intramolecular palladium‐catalyzed direct arylation of thiophene‐3‐carbaldehyde or furan‐3‐carbaldehyde with 2‐haloanilines provided a one‐pot access to furo‐ or thienoquinolines in high yields with H 2 O and HBr as the major waste. Both electron‐withdrawing and ‐donating substituents on the 2‐haloaniline derivatives were tolerated. These furo‐ or thienoquinoline derivatives can be employed in the direct arylation at C‐5 of the furyl or thienyl moiety, and a variety of corresponding arylation products were obtained in high yields.