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The convergent syntheses of pyrazinyl and quinoxalinyl phenylmethanones from 2‐lithio pyrazines and quinoxalines
Author(s) -
Ward John S.,
Merritt Leander
Publication year - 1991
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.5570280336
Subject(s) - chemistry , metalation , ketone , lithium (medication) , reagent , nucleophile , medicinal chemistry , organic chemistry , medicine , endocrinology , catalysis
Pyrazines and quinoxalines bearing 2‐substituents that direct ortho metalation reacted with lithium 2,2,6,6‐tetramethylpiperidide to produce 2‐substituted‐3‐lithiopyrazines and quinoxalines. These lithio reagents reacted with N ‐methoxy‐ N ‐methylbenzamide to give good to moderate yields of 3‐substituted pyrazinyl or quinoxalinylphenylmethanones. The 3‐methylthio substituents of some ketone products were oxidized to methylsulfonyl groups that were susceptible to nucleophilic displacement.