Open AccessSuperelectrophiles in Synthesis: Preparation of Aromatic Imides
Author(s) -
Sean H. Kennedy,
Mark N. Schaeff,
Douglas A. Klumpp
Publication year - 2019
Publication title -
journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.2
H-Index - 228
eISSN - 1520-6904
pISSN - 0022-3263
DOI - 10.1021/acs.joc.9b01437
Subject(s) - chemistry , imide , isocyanate , electrophile , triflic acid , carboxylic acid , organic chemistry , acylation , carbamic acid , combinatorial chemistry , catalysis , polyurethane
Aromatic carboxylic acids are found to undergo reactions with isocyanates, wherein triflic acid promotes the formation of aromatic imide products in fair to good yields. It is proposed that the carboxylic acid group directs the isocyanate electrophile to the ortho -position. This is thought to occur by the formation of a temporary carbamic acid anhydride group, which cleaves upon ortho -functionalization. A series of imide products are synthesized, and the synthesis of a potential selective inhibitor of tyrosyl DNA phosphodiesterase II is performed.