A FACILE SYNTHESIS OF FLUORINE-CONTAINING 1,7-PHENANTHROLINES BY THE CYCLIZATION OF N-PROPARGYL-6,8-BIS(TRIFLUOROACETYL)QUINOLIN-5-AMINE WITH VARIOUS ACTIVE METHYLENE COMPOUNDS

The reaction of N-propargyl-6,8-bis(trifluoroacetyl)quinolin-5-amine (1) with various active methylene compounds gave the novel fluorine-containing 1,7-phenanthroline derivatives (3). Furthermore, changing the electron-withdrawing groups on active methylene compounds induced interesting alternation...

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Bibliographic Details
Published inHeterocycles Vol. 82; no. 1; pp. 803 - 812
Main Authors Shibata, Dai, Sakai, Ayaka, Hatakenaka, Mizuki, Saikawa, Shohei, Kamitori, Yasuhiro, Medebielle, Maurice, Okada, Etsuji
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 31.12.2010
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
1,7-Phenanthrolinone
EXCHANGE-REACTION
1,10-PHENANTHROLINES
ANALOGS
SULFIDES
N-Propargylquinoin-5-amine
Fluorine-Containing Heterocycle
CONTAINING HETEROCYCLIC-COMPOUNDS
1,7-Phenanthroline
AMINES
N,N-DIMETHYL-2,4-BISTRIFLUOROACETYL-1-NAPHTHYLAMINE
NUCLEOPHILIC N-N
PYRIDOQUINOLINES
DERIVATIVES
Active Methylene Compound
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Summary:The reaction of N-propargyl-6,8-bis(trifluoroacetyl)quinolin-5-amine (1) with various active methylene compounds gave the novel fluorine-containing 1,7-phenanthroline derivatives (3). Furthermore, changing the electron-withdrawing groups on active methylene compounds induced interesting alternation of the reaction site wherein the enolate anions attack first and led to construction of the different nitrogen-containing heterocyclic systems, 1,7-phenanthrolinone (4) and 1,4-dihydro-1,7-phenanthroline (5).
ISSN:0385-5414
DOI:10.3987/COM-10-S(E)71