127322-88-7Relevant academic research and scientific papers
Skeletal rearrangement in the Ritter reaction of turpentine: A novel synthesis of p-menthane diamides
Xu, Shi-Chao,Zhu, Shou-Ji,Chen, Yu-Xiang,Wang, Jing,Bi, Liang-Wu,Lu, Yan-Ju,Gu, Yan,Zhao, Zhen-Dong
, p. 124 - 127 (2017/03/14)
A novel skeletal rearrangement in the Ritter reaction was examined which conveniently generated p-menthane diamides from turpentine. A probable reaction mechanism was proposed based on employing thermodynamic analysis. All the products were purified and characterised by1H NMR, IR, X-ray crystallography and ESI+-MS.
Synthesis and Herbicidal Activities of p-Menth-3-en-1-amine and Its Schiff Base Derivatives
Zhu, Shouji,Xu, Shichao,Jing, Wang,Zhao, Zhendong,Jiang, Jianxin
, p. 9702 - 9707 (2017/01/06)
p-Menth-3-en-1-amine, 4, and its Schiff base derivatives, 5a-l, were designed and synthesized. They were characterized by FT-IR, ESI+-MS, HRMS, 1H NMR, and 13C NMR spectral analyses, and their pre-emergence herbicidal activities against ryegrass were evaluated. All of the compounds showed excellent herbicidal activity. The Schiff bases showed stronger herbicidal activities than the original amine 4. These compounds showed herbicidal activities comparable to that of glyphosate. The herbicidal activities of 5k and 5l against ryegrass shoot growth were 78.3 and 355.6% higher than that of glyphosate, respectively. Furthermore, the introduction of a chlorine or bromine atom into the Schiff base derivatives containing a furan or benzene ring was beneficial to increase the activity. However, the herbicidal activities were not clearly affected when the heteroatom of the five-membered heterocyclic Schiff base or the position of the substituent on pyridine Schiff base was altered.
ACID-CATALYZED TRANSFORMATIONS OF THE DERIVATIVES OF TERPENES IN THE BICYCLO- AND BICYCLOHEPTANE SERIES
Koval'skaya, S. S.,Kozlov, N. G.
, p. 1398 - 1407 (2007/10/03)
Under the conditions of acid catalysis the formation of the p-methane derivatives is the main direction in the transformations of pinane derivatives with reaction centers at C2 and C3 (α-pinene epoxide, 2α-hydroxypinan-3-one, 2α-hydroxypinan-3-one oxime, isopinocampheol and 3-phenylpinocampheol).Here, in the Ritter reaction thermodynamic factors give rise to the preferential formation of isomers with an equatorial acylamino group.The ability to react with nitriles under the conditions of acid catalysis with the formation of the geminal amides is a common feature of terpenoid ketones of the bicycloheptane series.The transformations of the terpenoid bicyclic oximes under the influence of sulfuric acid in aliphatic nitriles lead to the formation of two types of azabicyclic products - bicyclic lactams and bicyclic N-acylamidines.
SYNTHESIS OF (1S,5S,8R)-8-N-ACYLAMINO-2-ALKYL-4,4,8-TRIMETHYL-3-AZABICYCLONON-2-ENES FROM α-PINENE
Koval'skaya, S.S.,Kozlov, N.G.,Kalechits, G.V.
, p. 649 - 652 (2007/10/02)
(1R,2R,3R,5S)-2,6,6-Trimethylbicycloheptan-3-ol (isopinocampheol) obtained by the hydrogenation of (1S,5S)-α-pinene reacts with acetonitrile, propionitrile, and isobutyronitrile in the presence of concentrated sulfuric acid as a result of a series
STEREOSELECTIVE SYNTHESIS OF N,N'-DIACYL-p-MENTHANE-1,8-DIAMINES
Kovals'skaya, S. S.,Kozlov, N. G.,Tikhonova, T. S.
, p. 552 - 557 (2007/10/02)
It has been shown that the interaction of terpin hydrate with various nitriles under the conditions of the Ritter reaction takes place stereoselectively and leads to the formation of a mixture of isomeric cis- and trans-N,N'-diacyl-p-menthane-1,8-diamines in a ratio of 1:4.The structures of the products have been shown by 1H and 13C spectroscopy.
