Construction of benzo-fused indolizines, pyrrolo[1,2-a]quinolines via alkyne-carbonyl metathesis.
The strategic use of a sequential Sonogashira coupling/intramolecular alkyne-carbonyl metathesis process for the synthesis of a pyridine ring from 1-(2-haloaryl)-1H-pyrrole-2-carbaldehydes allowed ready access to diverse novel benzo-fused indolizines, pyrrolo[1,2-a]quinolines, in good to excellent yields. As a hybrid structure of indolizine and quinoline, the resulting scaffold has an acyl substituent at the C5 position, which is difficult to make by any other known approaches.
College of Pharmacy and Yonsei Institute of Pharmaceutical Sciences, Yonsei University, 85 Songdogwahak-ro, Yeonsu-gu, Incheon 406-840, Republic of Korea. ikyonkim@yonsei.ac.kr.
Maloy
M
Nayak
Ikyon
I
Kim
D000447:Aldehydes / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D007212:Indolizines / Q000737:chemistry*; D011804:Quinolines / Q000737:chemistry*
D000447:Aldehydes; D000480:Alkynes; D007212:Indolizines; D011804:Quinolines; C035094:indolizine; C037219:quinoline