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Alkaline condensation of 9,10‐phenanthrenedione with N,N ‐dialkylguanidines. A novel synthesis of 2′‐(dialkylamino)spiro[9 H ‐fluorene‐9,4′‐[4 H ]imidazol]‐5′(3′ H )ones
Author(s) -
Itano Harvey A.
Publication year - 1974
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.5570110640
Subject(s) - chemistry , fluorene , potassium hydroxide , medicinal chemistry , ring (chemistry) , condensation , stereochemistry , organic chemistry , polymer , physics , thermodynamics
9,10‐Phenanthrenedione was reacted with equimolar amounts of N,N ‐dimethylguanidine or creatine in 0.2 N potassium hydroxide in ethanol‐water, 7:3 to obtain 2′‐(dimethylamino)spiro‐[9 H ‐fluorene‐9,4′‐[4 H ]imidazol]‐5′(3′ H )one or N ‐(3′,5′‐dihydro‐5′‐oxospiro[9 H ‐fluorene‐9,4′‐[4 H ]imidazol]‐2′‐yl)‐ N ‐methylglycine, respectively. These products are the first derivatives of this ring system with 2′‐amino substituents. Formation of these products accounts for the previously reported absence of fluorescence when 9,10‐phenanthrenedione reacts with N,N ‐di‐substituted guanidines.