33489-99-5Relevant academic research and scientific papers
Effective nitration of anilides and acrylamides by tert-butyl nitrite
Ji, Yi-Fei,Yan, Hong,Jiang, Qi-Bai
, p. 2051 - 2060 (2015/03/18)
Nitro compounds are important intermediates in synthetic organic chemistry and the chemical industry. Herein, the efficient copper-catalyzed [10% Cu(NO3)2·3H2O] nitration of anilides was developed by using TBN (tert-butyl nitrite) as a nitrating reagent to give the corresponding nitro-substituted aromatic products in good to excellent yields. The use of TBN also led to the selective nitration of acrylamides at room temperature to afford only the (E) isomer of the nitration product. A series of anilides and acrylamides with a broad array of functional groups were well-tolerated by this procedure. This synthetic method has many advantages, which include inexpensive starting materials, mild reaction conditions, a fast reaction rate, and high yields. A mechanistic investigation indicates that a nitro radical, which is generated from the thermal homolysis of TBN, is involved in the two nitration processes. The efficient nitration of both anilides and acrylamides was achieved by using TBN (tert-butyl nitrite) as a metal-free nitrating reagent. This synthetic method has many advantages such as mild reaction conditions, a fast reaction rate, good to excellent yields, and a broad substrate scope. Our investigation indicates that a nitro radical is involved in the reaction mechanism.
Regioselective ortho-nitration of N-phenyl carboxamides and primary anilines using bismuth nitrate/acetic anhydride
Lu, Yang,Li, Yaming,Zhang, Rong,Jin, Kun,Duan, Chunying
supporting information, p. 9422 - 9427 (2013/10/08)
An efficient and one-pot synthetic method for the regioselective ortho-nitration of the N-phenyl carboxamides and primary anilines has been developed by using bismuth nitrate and acetic anhydride as the nitrating reagents. Reaction proceeds at room temperature and results in corresponding ortho-nitrated products in moderate to excellent yields. This method provides an operationally simple, regioselective, and efficient access to synthesize o-nitro anilines under the mild conditions.
Facile synthesis of thiazoles via an intramolecular thia-Michael strategy
Sasmal, Pradip K.,Sridhar,Iqbal, Javed
, p. 8661 - 8665 (2007/10/03)
A mild and efficient method for the synthesis of substituted thiazoles is reported via one-pot N-desilylation, thioacylation/oxythioacylation/thiothioacylation followed by thia-Michael cycloisomerisation. This method has a general applicability to introdu
A mild and efficient procedure for the conversion of aromatic carboxylic esters to secondary amides
Arora, Revika,Paul, Satya,Gupta, Rajive
, p. 1137 - 1140 (2007/10/03)
A mild and efficient procedure has been developed for the conversion of aromatic carboxylic esters to secondary amides using reusable Zn dust with microwave heating in the presence of N,N-dimethylformamide or conventional heating by stirring in an oil bath using THF as solvent. Zn dust can be reused several times after simple washing with dil. HC1 and distilled water.
