Anionic N-Fries rearrangement of N-alkyl-2-iodo anilides induced by iodine-magnesium exchange: application for synthesis of strained 1,2,3-trisubstituted indoles.
A superior, mild, high-yielding one-pot process for rapid access to oxo anilides has been developed that involves three cascade reactions: iodine-magnesium exchange, regiospecific ortho N-Fries rearrangement, and in situ trapping of the formed aniline anion. Coupled with McMurry cyclization, the two-step process allows ready synthesis of strained 1,2,3-trisubstituted indoles regioselectively.
Ding
Fei
F
Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals Inc., Ridgefield, CT 06877, USA.
Zhang
Yongda
Y
Qu
Bo
B
Li
Guisheng
G
Farina
Vittorio
V
Lu
Bruce Z
BZ
Senanayake
Chris H
CH
D000813:Anilides / Q000737:chemistry*; D000838:Anions; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D007455:Iodine / Q000737:chemistry*; D008274:Magnesium / Q000737:chemistry*
D000813:Anilides; D000838:Anions; D007211:Indoles; D007455:Iodine; D008274:Magnesium