title: Access to functionalized 3H-pyrrolo[2,3-c]quinolin-4(5H)-ones and thieno[2,3-c]quinolin-4(5H)-ones via domino reaction of 4-alkynyl-3-bromoquinolin-2(1H)-ones.
abstract: We describe two efficient protocols for the straightforward synthesis of 3H-pyrrolo[2,3-c]quinolin-4(5H)-one and thieno[2,3-c]quinolin-4(5H)-one derivatives from readily available 4-alkynyl-3-bromoquinolin-2(1H)-one as precursor. The efficient synthesis of highly functionalized 3H-pyrrolo[2,3-c]quinolin-4(5H)-ones has been achieved via a palladium-catalyzed domino reaction of 4-alkynyl-3-bromoquinolin-2(1H)-ones with amines. Thieno[2,3-c]quinolin-4(5H)-one derivatives were also conveniently synthesized via sequential nucleophilic aromatic substitution/5-endo-dig cyclization between 4-alkynyl-3-bromoquinolin-2(1H)-ones and sodium sulfide with good functional tolerance under mild conditions.
authors.affiliation: School of Chemistry and Chemical Engineering, Chongqing University , Chongqing 400044, P. R. China.
authors.forename: Zhiyong
authors.initials: Z
authors.lastname: Wang
authors.forename: Lijun
authors.initials: L
authors.lastname: Xue
authors.forename: Yiyi
authors.initials: Y
authors.lastname: He
authors.forename: Licong
authors.initials: L
authors.lastname: Weng
authors.forename: Ling
authors.initials: L
authors.lastname: Fang
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry*; D015363:Quinolones / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: C000597350:3H-pyrrolo(2,3-c)quinolin-4(5H)-one; D000480:Alkynes; D011758:Pyrroles; D015363:Quinolones; C000597352:thieno(2,3-c)quinolin-4(5H)-one; D010165:Palladium