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Interaction of alkali metals with unsaturated heterocyclic compounds. The reductive metalation of 1,4‐diphenylphthalazine
Author(s) -
Kaban Seniz
Publication year - 1986
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.5570230104
Subject(s) - chemistry , metalation , annulation , alkylation , alkali metal , reagent , protonation , acylation , tetrahydrofuran , medicinal chemistry , ring (chemistry) , organic chemistry , ion , solvent , catalysis
1,4‐Diphenylphthalazine ( 1 ) was reduced in tetrahydrofuran by sodium metal to a monomeric dianion 2 . Chemical reactions of this new dianion were examined with various reagents. Generally, the protonation, acylation and alkylation products were 1,2‐dihydrophthalazine derivatives. An annulation of the phthalazine ring system was accomplished by treating the dianion with 1,3‐dichloropropane or 1,4‐dichlorobutane. With 1,2‐dichloroethane however, only 1,4‐diphenylnaphthalene was detected.