The regioselective iodination of quinolines, quinolones, pyridones, pyridines and uracil.
A radical based direct C-H iodination protocol for quinolines, quinolones, pyridones, pyridines, and uracil has been developed. The iodination occurs in a C3 selective manner for quinolines and quinolones. Pyridones and pyridines undergo C3 and C5 iodination, while dimethyl uracil undergoes C5 iodination. Scope of the method was demonstrated through the rapid synthesis of both electron rich as well as electron poor heteroaromatic iodides. The protocol was found to be scalable and general, while a mechanism has been proposed.
Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai - 400076, India. dmaiti@chem.iitb.ac.in and IITB-Monash Research Academy, CSE Building, IIT Bombay, Powai, Mumbai - 400076, India.
Uttam
U
Dutta
Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai - 400076, India. dmaiti@chem.iitb.ac.in.
Arghya
A
Deb
IITB-Monash Research Academy, CSE Building, IIT Bombay, Powai, Mumbai - 400076, India and School of Chemistry, Monash University, Clayton 3800, Victoria, Australia. david.lupton@monash.edu.
David W
DW
Lupton
Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai - 400076, India. dmaiti@chem.iitb.ac.in and IITB-Monash Research Academy, CSE Building, IIT Bombay, Powai, Mumbai - 400076, India.
Debabrata
D
Maiti
D054879:Halogenation; D007455:Iodine / Q000737:chemistry*; D007536:Isomerism; D008956:Models, Chemical; D011728:Pyridones / Q000138:chemical synthesis* / Q000737:chemistry; D015363:Quinolones / Q000138:chemical synthesis* / Q000737:chemistry; D014498:Uracil / Q000138:chemical synthesis* / Q000737:chemistry
D011728:Pyridones; D015363:Quinolones; D014498:Uracil; D007455:Iodine