40412-00-8Relevant academic research and scientific papers
A facile protocol for the synthesis of mono-N-methyl anilines via formimidate intermediates
Sun, Nan,Wang, Shuai,Mo, Weimin,Hu, Baoxiang,Shen, Zhenlu,Hu, Xinquan
experimental part, p. 7142 - 7148 (2010/09/14)
A general procedure for the preparation of mono-N-methyl anilines has been developed with excellent yields. This protocol relies on a NaBH3(OAc) reduction of formimidate intermediates that are quantitatively generated by treatment of primary substituted anilines with triethyl orthoformate under the catalysis of MCM-41-SO3H mesoporous zeolite. The newly developed procedure was facile, efficient, and environmentally benign.
Insight into the mechanism of three component condensation leading to aminomethylenebisphosphonates
Dabrowska, Ewa,Burzyńska, Agnieszka,Mucha, Artur,Matczak-Jon, Ewa,Sawka-Dobrowolska, Wanda,Berlicki, ?ukasz,Kafarski, Pawe?
experimental part, p. 3806 - 3813 (2010/03/03)
Three-component reaction of a primary amine, diethyl phosphite and triethyl orthoformate followed by acid hydrolysis of the adduct provides N-substituted aminomethylenebisphosphonic acids in good yields. Being extremely versatile, it is commonly utilized for preparation of compounds possessing potential antiosteoporotic, antibacterial, anticancer, antiparasitic or herbicidal activity. However, the mechanism of the reaction remains unknown. p-Nitroaniline has been found an interesting tool to shed light on this matter. Its use allowed to separate and identify four intermediates, both non-phosphorus and phosphorus containing, and subsequently suggest the mechanism of the whole process. The acquired knowledge was helpful in explanation the route and the final product structure obtained for more complex reaction proceeding with the use of 4-aminopyridine. Additional alkylation of the pyridine nitrogen atom, leading to unexpected N-(1-alkylpyridinium-4-amino)methylenebisphosphonic acids was unambiguously proved.
Amidines. I. Hydrolysis of N1-acyl- and N1-tosyl-N1,N2-diarylamidines
Ono,Tamura
, p. 590 - 596 (2007/10/02)
In acid hydrolysis of N1-acyl-N1,N2-diarylamidines, a water molecule attacked exclusively the amidine central carbon, and the reaction proceeded in parallel through two pathways. One of them leads to the formation of two N-acylarylamines, and the other leads to the formation of N,N-diacylarylamine and arylamine. Acid hydrolysis of N1-tosyl-N1,N2-diarylamidine was also examined. The results were similar to those of the hydrolysis of N1-acyl-N1,N2-diarylamidines. Alkaline hydrolysis and alcoholysis of N1-acyl-N1,N2-diarylamidines occurred almost exclusively at the amide carbonyl group to give N1,N2-diarylamidines and carboxylic acids or their esters. The effects of structural change and the aryl substituents on the rate and direction of the reaction were examined.
