The chemistry of polycyclic arene imines. III.  N ‐alkylation of phenanthrene 9,10‐imine  N ‐alkylation of phenanthrene 9,10‐imine | Zendy

Shtelzer Sarah | Zendy; Weitzberg Moshe | Zendy; Jeries Juliette | Zendy; Sheradsky Tuvia | Zendy; Aizenshtat Zeev | Zendy; Blum Jochanan | Zendy

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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.

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