The preparation of some 2-nitroacridines and related compounds

1981 ◽  
Vol 34 (4) ◽  
pp. 839 ◽  
Author(s):  
J Rosewear ◽  
JFK Wilshire
Keyword(s):  
Acid Solution ◽  
Trifluoroacetic Acid ◽  
Ion Treatment ◽  
Related Compounds

The reaction of 2-fluoro-5-trobenzaldehyde with a wide variety of arylamines gives, in general, mixtures of the corresponding 2-arylamino-5-nitrobenzaldehydes and their related anils. Both aldehydes and anils readily underwent acid-catalysed cyclization to give the corresponding 2-nitro-acridines. The effect of substituent on the rate of cyclization of these aldehydes and of some related anilino-benzaldehydes and -acetophenones has been studied in trifluoroacetic acid solution by means of 1H n.m.r. spectroscopy. A solution of 2-(N-methylanilino)-5-nitrobenzaldehyde in trifluoroacetic acid appears to contain a substituted acridinium ion; treatment of this solution with alkali gave 10-methyl-2-nitroacridone. 1H n.m.r. data for a wide variety of substituted 2-nitro-acridines are discussed.

ChemInform Abstract: Ozonization of Perfluoroolefins in Trifluoroacetic Acid Solution.

ChemInform ◽  
1990 ◽  
Vol 21 (5) ◽  
Author(s):  
N. I. MOISEEVA ◽  
A. E. GEKHMAN ◽  
E. S. RUMYANTSEV ◽  
V. I. KLIMANOV ◽  
I. I. MOISEEV
Keyword(s):  
Acid Solution ◽  
Trifluoroacetic Acid

Nucleic acid related compounds. 78. Stereocontrolled syntheses of 6′(E and Z)-halovinyl analogues from uridine-derived vinylsulfones via vinyltin intermediates

1993 ◽  
Vol 71 (2) ◽  
pp. 192-198 ◽  
Author(s):  
Stanislaw F. Wnuk ◽  
Morris J. Robins
Keyword(s):  
Nucleic Acid ◽  
Trifluoroacetic Acid ◽  
Bond Cleavage ◽  
Lead Tetraacetate ◽  
Acetylenic Derivative ◽  
Vinyl Derivative ◽  
High Yields ◽  
Related Compounds

Treatment of the 6′(E)-tosylvinyl homonucleoside 1a with Bu3SnH/AIBN/toluene/Δ gave separable mixtures of 6′-vinylstannanes 2a(E/Z) in high yields. Stereospecific halodestannylations with N-iodosuccinimide, bromine, and N-bromosuccinimide proceeded smoothly to give the 6′(E or Z)-iodo(and bromo) vinyl compounds with retention of configuration. Chlorine or iodobenzene dichloride effected moderately stereoselective chlorodestannylation. Treatment of 2a with NH4F/MeOH/Δ resulted in carbon–tin bond cleavage to give the free vinyl derivative 4a. Aqueous trifluoroacetic acid effected concomitant protiodestannylation and deprotection of 2a to give 4b. Treatment of 2a(E) with lead tetraacetate/acetonitrile and deprotection afforded acetylenic derivative 3b.

Ozonation of perfluoroolefins in trifluoroacetic acid solution

1989 ◽  
Vol 38 (7) ◽  
pp. 1570-1570 ◽  
Author(s):  
N. I. Moiseeva ◽  
A. E. Gekhman ◽  
E. S. Rumyantsev ◽  
V. I. Klimanov ◽  
I. I. Moiseev
Keyword(s):  
Acid Solution ◽  
Trifluoroacetic Acid

Oxidative Coupling of Lignans. III. Non-Phenolic Oxidative Coupling of Deoxypodorhizon and Related Compounds

1988 ◽  
Vol 41 (6) ◽  
pp. 897 ◽  
Author(s):  
RC Cambie ◽  
PA Craw ◽  
PS Rutledge ◽  
PD Woodgate
Keyword(s):  
Trifluoroacetic Acid ◽  
Oxidative Coupling ◽  
Phenolic Substances ◽  
Related Compounds

Oxidative coupling of deoxypodorhizon (4) with thallium(III) oxide and trifluoroacetic acid may be controlled to give either deoxyisopodophyllotoxin (14) or isostegane (16). These results and those with related non- phenolic substances indicate that the aromatic substituents of the parent diarylbutane play an important role in determining the outcome of oxidative coupling.

scholarly journals The free-radical phenylation of isoquinolinium cation

1982 ◽  
Vol 35 (10) ◽  
pp. 2179 ◽  
Author(s):  
AJ Beveridge ◽  
LK Dyall
Keyword(s):  
Free Radical ◽  
Acid Solution ◽  
Trifluoroacetic Acid ◽  
Theoretical Predictions ◽  
Radical Phenylation

Free-radical phenylation of isoquinolinium cation has been effected by photolysis of phenylthalliurn(III)di(trifluoroacetate) in a trifluoroacetic acid solution of isoquinoline. Analysis (g.l.c. and h.p.l.c.) of the isomeric phenylisoquinoline mixture showed that the dominant product (81.1 %) was 1-phenylisoquinoline, in accordance with two published theoretical predictions.

REACTIONS OF AMIDES AND RELATED COMPOUNDS: III. N.M.R. INVESTIGATION OF THE PROTONATION OF N,N-DIMETHYLNITROSOAMINE, N,N-DIETHYLNITROSOAMINE, AND N-NITROSOPIPERIDINE

1966 ◽  
Vol 44 (2) ◽  
pp. 105-109 ◽  
Author(s):  
Stephen J. Kuhn ◽  
John S. McIntyre
Keyword(s):  
Sulfuric Acid ◽  
Magnetic Resonance ◽  
Perchloric Acid ◽  
Trifluoroacetic Acid ◽  
Proton Magnetic Resonance ◽  
Acid Solutions ◽  
Concentrated Sulfuric Acid ◽  
Related Compounds ◽  
Equimolar Solution ◽  
Magnetic Resonance Spectra

Protonation of N,N-dimethylnitrosoamine has been investigated by dissolving the nitrosoamine in different acids and recording the proton magnetic resonance spectra of these solutions. Concentrated sulfuric acid, sulfuric acid monohydrate, perchloric acid (72%), trifluoroacetic acid, and fluorosulfuric acid have been used in this study. Only in fluorosulfuric acid near 0 °C and lower was a new signal observed for the protonated nitrosoamine molecule. Integration of the peaks has shown that only one proton is captured by the nitrosoamine. The following structure is suggested for the protonated nitrosoamine.[Formula: see text]The n.m.r. spectra of fluorosulfuric acid solutions of N,N-diethylnitrosoamine and N-nitrosopiperidine also show separate signals for the captured proton.The n.m.r. spectrum of an equimolar solution of N,N-dimethylnitrosoamine, N,N-dimethylformamide, and trifluoroacetic acid in 2-nitropropane indicates that N,N-dimethylnitrosoamine is a weaker base.

Sign in / Sign up

Export Citation Format

Share Document