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Vicarious Nucleophilic Substitution in Nitroquinolines 1)
Author(s) -
Mąkosza Mieczyslaw,
Kinowski Andrzej,
Danikiewicz Witold,
Mudryk Boguslaw
Publication year - 1986
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.198619860107
Subject(s) - carbanion , chemistry , sulfone , nucleophilic substitution , acetonitrile , nitro , acetonitriles , medicinal chemistry , substitution reaction , stereochemistry , nucleophilic aromatic substitution , organic chemistry , alkyl
5‐Nitro‐, 6‐nitro‐, and 8‐nitroquinoline react with the carbanions of chloromethyl phenyl sulfone, chloro‐ N,N ‐dimethylmethanesulfonamide and substituted acetonitriles XCH 2 CN (X = OPh, SPh, Cl) giving products of the vicarious nucleophilic substitution of hydrogen predominantly or exclusively at positions 6, 5, and 7, respectively. A different orientation pattern and sometimes other reaction pathways are observed in reactions involving tertiary carbanions of (phenoxy)(phenyl)acetonitrile and 1‐chloropropyl p ‐tolyl sulfone. The 1 H NMR spectra of the substitution products are discussed in connection with their structures.