Unexpected domino reaction via Pd-catalyzed Sonogashira coupling of benzimidoyl chlorides with 1,6-enynes and cyclization to synthesize quinoline derivatives.
A domino reaction via palladium-catalyzed Sonogashira coupling of benzimidoyl chlorides with 1,6-enynes and then cyclization to form quinoline derivatives has been developed. The reaction conditions and the scope of the process are examined, and a plausible mechanism is proposed. The procedure is simple, rapid, and general, and the substrates are readily available.
Gao
Guo-Lin
GL
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, People's Republic of China.
Niu
Yan-Ning
YN
Yan
Ze-Yi
ZY
Wang
Hong-Li
HL
Wang
Gang-Wei
GW
Shaukat
Ali
A
Liang
Yong-Min
YM
D000480:Alkynes / Q000737:chemistry*; D001549:Benzamides / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D013329:Structure-Activity Relationship
D000480:Alkynes; D001549:Benzamides; D011804:Quinolines; D010165:Palladium; C037219:quinoline