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A New Indole Synthesis Promoted by Metal Triflates
Author(s) -
Kozikowski Alan P.,
Cheng XueMin,
Li ChunSing,
Scripko James G.
Publication year - 1986
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1002/ijch.198600011
Subject(s) - chemistry , indole test , trifluoromethanesulfonate , nitrile , ketone , combinatorial chemistry , metal , zinc , organic chemistry , catalysis
A new synthesis of 4‐ and 7‐ carbon ‐substituted indoles is described. The overall sequence involves the addition of a nitrile oxide to 1 carboethoxy‐2‐(or 3‐) allylpyrrole, hydrogenation of the intermediate isoxazoline to β ‐hydroxy ketone and cyclization of the ketol using magnesium or zinc triflate to the substituted indole. This new indole‐forming strategy can also accommodate the introduction of oxygen functionality into the indole 6‐position. Possible mechanistic aspects of the reaction are detailed.