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Condensation of 1‐(Dicyanomethylene)acenaphthene‐2‐one with Aromatic Diamines
Author(s) -
ElShaieb Kamal M.
Publication year - 2008
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.200800169
Subject(s) - chemistry , hydrazine (antidepressant) , acetonitrile , medicinal chemistry , hydrate , acetonitriles , acenaphthene , quinoxaline , condensation , diol , condensation reaction , organic chemistry , catalysis , phenanthrene , physics , chromatography , thermodynamics
1‐(Dicyanomethylene)acenaphthene‐2‐one ( 1 ) reacts with 1,8‐diaminonaphthalene ( 2 ) to yield two products, identified as acenaphtho[1,2‐ b ]naphtho[1,8‐ ef ][1,4]diazepine ( 3 ) and ( Z )‐2‐(8‐aminonaphthalen‐1‐ylamino)‐2‐(2‐oxoacenaphthylen‐1(2 H )‐ylidene)acetonitrile ( 4 ). On the other hand, (2 Z ,2′ Z )‐2,2′‐(hydrazine‐1,2‐diylidene)diacenaphthylen‐1(2 H )‐one ( 6 ) was obtained during the condensation process of 1 with hydrazine hydrate ( 5 ). Reaction of 1 with 3,4‐diaminotoluene ( 8b ) produces 9‐methylacenaphtho[1,2‐ b ]quinoxaline ( 9b ) and ( Z )‐2‐(2‐amino‐5‐methylphenyl‐amino)‐2‐(2‐oxoacenaphthylen‐1(2 H )‐ylidene)acetonitrile ( 10b ). However, treatment of 5,6‐diamino‐pyrimidine‐2,4‐diol hemisulphate ( 11 ) with 1 affords acenaphtho[1,2‐ g ]pteridine‐9,11‐diol ( 12 ).