On the Nucleophilic Reactivity of 4,6-Dichloro-5-nitrobenzofuroxan with Some Aliphatic and Aromatic Amines: Selective Nucleophilic Substitution

2020 ◽  
Vol 85 (21) ◽  
pp. 13472-13480 ◽  
Author(s):  
Elena Chugunova ◽  
Vincenzo Frenna ◽  
Giovanni Consiglio ◽  
Gabriele Micheletti ◽  
Carla Boga ◽  
...  
Keyword(s):  
Nucleophilic Substitution ◽  
Aromatic Amines ◽  
Nucleophilic Reactivity

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.

scholarly journals 4,6-Dichloro-5-Nitrobenzofuroxan: Different Polymorphisms and DFT Investigation of Its Reactivity with Nucleophiles

2021 ◽  
Vol 22 (24) ◽  
pp. 13460
Author(s):  
Elena Chugunova ◽  
Nurgali Akylbekov ◽  
Alexey Dobrynin ◽  
Alexander Burilov ◽  
Carla Boga ◽  
...  
Keyword(s):  
Dft Calculations ◽  
Nucleophilic Substitution ◽  
Nitro Group ◽  
Kinetic Data ◽  
Aromatic Nucleophilic Substitution ◽  
X Ray ◽  
Nucleophilic Reactivity ◽  
Amino Derivatives ◽  
Torsional Angles

This research focuses on the X-ray structure of 4,6-dichloro-5-nitrobenzofuroxan 1 and of some of its amino derivatives (4a, 4e, 4g, and 4l) and on DFT calculations concerning the nucleophilic reactivity of 1. We have found that by changing the solvent used for crystallization, it is possible to obtain 4,6-dichloro-5-nitrobenzofuroxan (1) in different polymorphic structures. Moreover, the different torsional angles observed for the nitro group in 1 and in its amino derivatives (4a, 4e, 4g, and 4l) are strictly dependent on the steric hindrance of the substituent at C-4. DFT calculations on the course of the nucleophilic substitution confirm the role of the condensed furoxan ring in altering the aromaticity of the carbocyclic frame, while chlorine atoms strongly influence the dihedral angle and the rotational barrier of the nitro group. These results corroborate previous observations based on experimental kinetic data and give a deep picture of the reaction with amines, which proceeds via a “non-aromatic” nucleophilic substitution.

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.

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.

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

The remarkable effect of 7-amino substituents on the reactivity of 4-nitrobenzofurazans with nucleophiles

2005 ◽  
Vol 83 (9) ◽  
pp. 1222-1227 ◽  
Author(s):  
Michael R Crampton ◽  
Chukwuemeka Isanbor ◽  
Thomas C Willett
Keyword(s):  
Nucleophilic Substitution ◽  
Key Words ◽  
Alkaline Solution ◽  
Equilibrium Constants ◽  
Remarkable Effect ◽  
Iminium Ion ◽  
Nucleophilic Reactivity ◽  
Conjugate Bases ◽  
Sulfite Ions

The reactions of four 4-nitrobenzofurazans (4a–4d) substituted at the 7 position with (a) N-ethyl, (b) N-butyl, (c) piperidino, or (d) pyrrolidino groups have been examined with sulfite ions and with hydroxide ions in water–DMSO (80:20, v/v). Addition of sulfite at the 5 position gives σ adducts with equilibrium constants ca. 105 lower than that for the formation of the corresponding adduct from 4-nitrobenzofurazan. These reductions are attributed to the stabilization of the parent molecules 4a–4d by conjugative interaction between the 4 and 7 substituents. In alkaline solution, 4a and 4b yield the conjugate bases while 4c and 4d suffer nucleophilic substitution to give 7-hydroxy-4-nitrobenzofurazan. Reactivity here is relatively high because of the iminium ion character of the substrates. Key words: benzofurazans, σ adducts, nucleophilic reactivity, substitution.

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