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Studies on pyrazines. Part 28 . Deoxydative acetoxylation of pyrazine N ‐oxides
Author(s) -
Sato Nobuhiro,
Miwa Naoko,
Suzuki Hiroko,
Sakakibara Tohru
Publication year - 1994
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570310520
Subject(s) - chemistry , regioselectivity , pyrazine , triethylamine , medicinal chemistry , organic chemistry , bromide , zinc , catalysis
Abstract Deoxydative acetoxylation of 3‐methoxy‐, 3‐phenyl‐, 3‐methyl‐, 3‐chloro‐, and 3‐methoxycar‐bonylpyrazine 1‐oxides furnished predominantly 2‐acetoxy‐6‐substituted pyrazines, some of which were more selectively prepared by addition of zinc bromide and triethylamine to the reaction. Regioselectivity of the acetoxylation is discussed based upon heat of formation by AMI and AMI‐COSMO for all possible isomers of each set.