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Pd‐Catalyzed ortho Selective C–H Acyloxylation and Hydroxylation of Pyridotriazoles
Author(s) -
Rawat Deepa,
Kumar Rahul,
Adimurthy Subbarayappa
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201901748
Subject(s) - chemistry , acetic anhydride , catalysis , reagent , hydroxylation , acylation , yield (engineering) , hydrolysis , organic chemistry , medicinal chemistry , ring (chemistry) , enzyme , materials science , metallurgy
An efficient protocol for the palladium‐catalyzed direct ortho C–H acyloxylation of 3‐phenyl‐pyridotriazoles is described. The reaction was facilitated by PhI(OAc) 2 (PIDA) as an oxidant and with carboxylic acids as acyloxylation reagents. The reaction is highly selective for mono acyloxylation of pyridotriazoles with various acids such as aliphatic, branched, and cyclic including adamantane carboxylic acids. When acetic anhydride was employed as acylation reagent, interesting 2‐oxo‐1‐phenyl‐1‐(pyridin‐2‐yl)propyl acetates were obtained through the ring opening of pyridotriazoles. The key strategy is the employment of pyridotriazoles as a modifiable heterocycle; acyloxylation followed by the hydrolysis in one pot to yield the potential drug intermediates [(2‐hydroxyphenyl)pyridin‐2‐yl]methanone in good yields.