Regiospecific Nucleophilic Substitution of Fluorine in Fused Tetrafluoroquinolines with N- and O-Nucleophiles

2002 ◽  
Vol 2002 (8) ◽  
pp. 357-358 ◽  
Author(s):  
Michael A. Abramov ◽  
Suzanne Toppet ◽  
Wim Dehaen
Keyword(s):  
Nucleophilic Substitution ◽  
Aromatic Amines

5,6,7,8-Tetrafluoro-1,2-azolo[3,4- b;4′,3′- e]quinolines react regiospecifically with aliphatic and aromatic amines, alcohols and phenols yielding 7-substituted 5,6,8-trifluoro-1,2-azolo[3,4- b;4′,3′- e]quinolines.

Lewis-Acid-Catalyzed Direct Nucleophilic Substitution Reaction of Alcohols for the Functionalization of Aromatic Amines

2019 ◽  
Vol 4 (4) ◽  
pp. 1371-1374 ◽  
Author(s):  
Onkar S. Nayal ◽  
Maheshwar S. Thakur ◽  
Rohit Rana ◽  
Rahul Upadhyay ◽  
Sushil K. Maurya
Keyword(s):  
Nucleophilic Substitution ◽  
Lewis Acid ◽  
Aromatic Amines ◽  
Substitution Reaction ◽  
Nucleophilic Substitution Reaction ◽  
Acid Catalyzed

scholarly journals Synthesis and Antifungal Studies of (2E)-N-Benzyl-N′-phenylbut-2-enediamide and (2E)-N,N′-Dibenzylbut-2-enediamide Analogues

2013 ◽  
Vol 2013 ◽  
pp. 1-7 ◽  
Author(s):  
Habila J. Dama ◽  
Kandappa H. Reddy ◽  
Patrick Govender ◽  
Neil A. Koorbanally
Keyword(s):  
Maleic Anhydride ◽  
Nucleophilic Substitution ◽  
Aromatic Amines ◽  
Phenyl Ring ◽  
Fungal Species ◽  
Broth Microdilution ◽  
Microdilution Method ◽  
Yeast Strains ◽  
Broth Microdilution Method

A series of eleven butanediamine analogues, of which nine were new, were synthesized by the nucleophilic substitution of aromatic amines and benzylamines with maleic anhydride and tested on four yeast strains ofCandidaspecies using the broth microdilution method. Compounds3aand3cwith an unsubstituted phenyl ring and a 3-methoxyphenyl ring, respectively, are the most active against the fungal species with MIC values ranging from 20.2 to 80.6 μM forC. albicansandC. parapsilosisand 178.5 and 161.2 μM forC. krusei, respectively.

The Nucleophilic Substitution Reactions of 5- and 7-Chloro-4,6-dinitrobenzofurazan 1-Oxide by Aromatic Amines.

1985 ◽  
Vol 38 (3) ◽  
pp. 435 ◽  
Author(s):  
RW Read ◽  
WP Norris
Keyword(s):  
Nucleophilic Substitution ◽  
Aromatic Amines ◽  
Equilibrium Mixture ◽  
Substitution Reactions ◽  
Isomeric Mixture ◽  
Nucleophilic Substitution Reactions ◽  
Mild Conditions ◽  
Structural Assignment

7-Chloro-4,6-dinitrobenzofurazan 1-oxide is a powerful electrophile which reacts with a variety of primary and secondary aromatic amines, even those with deactivating substituents , to give arylamino - benzofurazan oxides under mild conditions. Tertiary aromatic amines react through carbon to give aminoarylbenzofurazan oxides. During, or as a consequence of, the substitution reactions, tautomerism occurs to give in all but one example an equilibrium mixture of 5- and 7-substituted 4,6-dinitrobenzofurazan oxides in which the latter predominates. Thus 5-chloro-4,6-dinitrobenzofurazan 1-oxide and 7- chloro-4,6-dinitrobenzofurazan 1-oxide both react with aniline to yield the same isomeric mixture of products: 4,6-dinitro-7- phenylaminobenzofurazan oxide (predominantly 1-oxide) (major) and 4,6- dinitro-5-phenylaminobenzofurazan 1-oxide (minor). The 5- and 7- phenylamino 4,6-dinitrobenzofurazans were prepared to assist in structural assignment of the N-oxides.

Aliphatic and aromatic 5-nitro-2-furylamines and aromatic 5-nitrofurfuryl ethers

1983 ◽  
Vol 48 (9) ◽  
pp. 2682-2692 ◽  
Author(s):  
Raul Mocelo ◽  
Jaroslav Kováč
Keyword(s):  
Nucleophilic Substitution ◽  
Aromatic Amines ◽  
Secondary Amines ◽  
Reaction Conditions ◽  
Primary Aromatic Amines

Tertiary 5-nitrofurylamines were prepared by a nucleophilic substitution of 5-nitro-2-furfuryl bromide (I) with aliphatic secondary amines. According to reaction conditions N-(5-nitro-2-furfuryl)-X-phenylamines or their mixture with N,N-di(5-nitro-2-furfuryl)-X-phenylamines were obtained from the reaction of I with substituted primary aromatic amines. Compound I gave with 2-aminophenol a mixture of O- and N-mono- and disubstituted derivatives, and with ethyl salicylate ethyl 2-(5-nitro-2-furfuryloxy)benzoate.

A highly α-regioselective In(OTf)3-catalyzed N-nucleophilic substitution of cyclic Baylis–Hillman adducts with aromatic amines

Tetrahedron ◽  
2009 ◽  
Vol 65 (17) ◽  
pp. 3473-3479 ◽  
Author(s):  
Yu-Liang Liu ◽  
Li Liu ◽  
Dong Wang ◽  
Yong-Jun Chen
Keyword(s):  
Nucleophilic Substitution ◽  
Aromatic Amines

ChemInform Abstract: Novel Mannich-Type Nucleophilic Substitution Reaction with Tertiary Aromatic Amines.

ChemInform ◽  
2010 ◽  
Vol 33 (30) ◽  
pp. no-no
Author(s):  
Hiroyasu Takahashi ◽  
Nobuyuki Kashiwa ◽  
Yuichi Hashimoto ◽  
Kazuo Nagasawa
Keyword(s):  
Nucleophilic Substitution ◽  
Aromatic Amines ◽  
Substitution Reaction ◽  
Nucleophilic Substitution Reaction

Reactions of 1-substituted 2,4-dinitrobenzenes with diamines and anilines : the question of base catalysis by amines

1975 ◽  
Vol 28 (11) ◽  
pp. 2521 ◽  
Author(s):  
HH Lee ◽  
L Main
Keyword(s):  
Charge Transfer ◽  
Nucleophilic Substitution ◽  
Rate Constants ◽  
Aromatic Amines ◽  
Aliphatic Amine ◽  
Base Catalysis ◽  
Complex Mechanism ◽  
Aromatic Nucleophilic Substitution ◽  
Second Stage ◽  
Catalytic Effects

Calculated second-order rate constants for the reactions of ethane-1,2- diamine and propane-1,3-diamine with 1-chloro-2,4-dinitrobenzene in methanol and with 2,4-dinitro-1-phenoxybenzene in dioxan/water (3 : 2) are mildly dependent on amine concentration. The catalysis is no weaker than that for monoamines and this is adduced as evidence suggesting that it does not represent base catalysis in the second stage of the intermediate-complex mechanism for activated aromatic nucleophilic substitution. ��� The aromatic amines m-anisidine, aniline, p-toluidine and p- anisidine mildly catalyse their own aminolysis reactions with 1-fluoro- 2,4-dinitrobenzene in methanol; the catalytic effects are not significantly smaller than that for the more strongly basic aliphatic amine butylamine. Contrary to an earlier report, there is no kinetic evidence to support charge-transfer complexing in the reaction of aniline with 1-fluoro-2,4-dinitrobenzene.

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