Photoinduced Reduction of Nitrobenzenes to Primary Aromatic Amines

Synlett ◽  
2017 ◽  
Vol 28 (10) ◽  
pp. 1191-1194 ◽  
Author(s):  
Gary Chuang ◽  
Hua-Hsuan Huang ◽  
Yu-Feng Chen ◽  
Guang-Hao Niu

Primary aromatic amines were synthesized from the corresponding nitrobenzenes via photoinduced reduction. The reaction was found to be effective when nitrobenzenes with electron-withdrawing substituents were irradiated with a broad band of UV light centered at 306 nm. When reactions are completed, products could be isolated by acid–base extraction or by column chromatography. This presenting photoreaction procedure for the synthesis of primary aromatic amines from the corresponding nitrobenzenes proceeds without the need of a sensitizer in isopropanol or THF. Without the usage of catalysts, or stoichiometric reducing reagent containing heavy metals, this photoinduced reduction of nitrobenzenes fulfils the concept of green chemistry.

2010 ◽  
Vol 2 (2) ◽  
pp. 322-329 ◽  
Author(s):  
M. M. Hossain ◽  
M. A. Foysal ◽  
M. Mahabub ◽  
Al- Amin

MW-assisted treatment of oximinoacetanilides obtained from substituted primary aromatic amines was carried out in conc. H2SO4 medium for 5-10 sec to give cyclic amides (isatins) through intramolecular cyclization by means of electrophilic aromatic substitution. Isatins reacted with thiosemicarbazide under MW-condition gave the corresponding Schiff-bases. The Schiff-bases undergo cyclization in presence of minimal Ac2O under MW-irradiation for 3-4 min to give the spiro-thiadiazoline acetyl derivatives in excellent yield. Keywords:  Microwave-synthesis; Isatins; Schiff-base; spiro-Thiadiazoline; Green chemistry. © 2010 JSR Publications. ISSN: 2070-0237 (Print); 2070-0245 (Online). All rights reserved.  DOI: 10.3329/jsr.v2i2.3731               J. Sci. Res. 2 (2), 322-329 (2010)  


2021 ◽  
Author(s):  
Goutam Brahmachari ◽  
Indrajit Karmakar ◽  
Pintu Karmakar

A one-pot procedure for the synthesis of biologically relevant coumarin-hydrazones by a three-component reaction between 4-hydrocoumarins, primary aromatic amines and tert-butyl nitrite under ball-milling in the absence of any catalyst/additive...


2020 ◽  
Vol 2020 ◽  
pp. 1-9
Author(s):  
Hassan Kabirifard ◽  
Pardis Hafez Taghva ◽  
Hossein Teimouri ◽  
Niloofar Koosheshi ◽  
Parastoo Javadpour ◽  
...  

The reaction of 4-benzoyl-5-phenylamino-2,3-dihydrothiophene-2,3-dione (1) with aminoheteroaryls, lamotrigine, 1,3-diaminoheteroaryls, dapsone, NH2R (hydroxylamine, DL-1-phenylethylamine, and metformin), and 4,4′-bipyridine in THF/H2O (1 : 1) at room temperature led to 3-N-phenylthiocarbamoyl-2-butenamides 2–5, while that with naphthylamines and 1,3-phenylenediamine in ethanol at high temperature led to 5-phenylamino-2,5-dihydrothiophene-2-ones 6–8 as organic ligands in the medium to good yields. These showed the nucleophilic attacks of N-nucleophiles, except primary aromatic amines, on thioester carboxyl group (C-2) of thiophene-2,3-dione ring 1. However, the nucleophilic attacks of primary aromatic amines on the carbonyl group (C-3) of thiophene-2,3-dione 1 occurred in the form of substituted thiophenes.


2010 ◽  
Vol 88 (9) ◽  
pp. 964-968 ◽  
Author(s):  
Zhaoqiong Jiang ◽  
Zhiqing Wu ◽  
Lixia Wang ◽  
Di Wu ◽  
Xiangge Zhou

A simple, highly efficient, and environmentally friendly protocol for the synthesis of primary aromatic amines by catalytic coupling of aromatic boronic acids with aqueous ammonia has been developed by using commercial and inexpensive CuSO4·5H2O as catalyst without addition of other solvents under mild reaction conditions.


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