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The chemistry of polycyclic arene imines. III. N ‐alkylation of phenanthrene 9,10‐imine N ‐alkylation of phenanthrene 9,10‐imine
Author(s) -
Shtelzer Sarah,
Weitzberg Moshe,
Jeries Juliette,
Sheradsky Tuvia,
Aizenshtat Zeev,
Blum Jochanan
Publication year - 1984
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.5570210101
Subject(s) - chemistry , phenanthrene , alkylation , imine , medicinal chemistry , halide , sodium hydride , organic chemistry , acenaphthene , alkyl , dichloromethane , catalysis , solvent
Phenanthrene 9,10‐imine ( 1 ) was shown to undergo N ‐alkylation without aziridine ring cleavage by (a) metallation with sodium methylsulfinylmethide followed by addition of an alkyl halide at −20° (b) reaction of 1 , sodium hydride and the halide in dimethylformamide at 40° (c) treatment of a dichloromethane solution of 1 , the halide and triethylbenzylammonium chloride with aqueous sodium hydroxide under phase transfer conditions. The syntheses of N ‐isopropyl‐, N ‐butyl‐, N ‐pentyl‐, N ‐allyl‐ and N ‐benzylphenanthrene 9,10‐imine ( 2–6 ) are described.