Alternating iodonium-mediated reaction cascades giving indole- and quinoline-containing polycycles.
A simple two-step convergent protocol gives direct access to synthetic intermediate A from ortho-iodoanilines. Intermediate A can be treated with NIS in CH2Cl2 to induce novel iodonium mediated domino reaction cascade, which provides direct access to ring-fused indole compounds B. Simply by changing the reaction conditions, this protocol can be directed down an alternative domino reaction cascade to give various ring fused quinoline compounds C.
Halim
Rosliana
R
Medicinal Chemistry and Drug Action, Monash Institute of Pharmaceutical Sciences, Monash University, 381 Royal Parade, Parkville, VIC 3052, Australia.
Scammells
Peter J
PJ
Flynn
Bernard L
BL
D000814:Aniline Compounds / Q000737:chemistry*; D003500:Cyclization; D007211:Indoles / Q000737:chemistry*; D015394:Molecular Structure; D009861:Onium Compounds / Q000737:chemistry*; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D011804:Quinolines / Q000737:chemistry*; D013237:Stereoisomerism
D000814:Aniline Compounds; D007211:Indoles; D009861:Onium Compounds; D011083:Polycyclic Compounds; D011804:Quinolines