Stereoselective synthesis of N,N′-diacyl-p-menthane-1,8-diamines

Kovals'skaya, S. S.; Козлов, Н. Г.; Tikhonova, T. S.

doi:10.1007/bf00598074

Cited by 12 publications

(10 citation statements)

References 2 publications

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“…N,N′-Diacetyl-p-menthane-1,8-diamine was synthesized using Ritter-type conditions according to a reported method. 26 First, 48 mL of 60% H 2 SO 4 and 23.8 g of terpin were added to a flask, and then 59.2 mL of acetonitrile was added dropwise to the reaction mixture using a constant-pressure funnel. The mixture was heated using an oil bath under continuous stirring using a magnetic stirrer.…”

Section: ■ Materials and Methodsmentioning

confidence: 99%

Synthesis and Herbicidal Activities of p-Menth-3-en-1-amine and Its Schiff Base Derivatives

Zhu

Wang

et al. 2016

J. Agric. Food Chem.

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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, H NMR, andC 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.

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Section: ■ Materials and Methodsmentioning

confidence: 99%

Synthesis and Herbicidal Activities of p-Menth-3-en-1-amine and Its Schiff Base Derivatives

Zhu

Wang

et al. 2016

J. Agric. Food Chem.

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“…Then, amide bonds were hydrolyzed under the catalysis of sodium hydroxide solution in EG to form p-menthane-1,8-diamine (MDA) (31). 275,276 Biobased PHUs were developed by the reaction of cyclic carbonated soybean oil with MDA (31) at 150 1C for a long time (60 h), similar to the synthesis of NIPUs, and without solvent, following a green chemistry approach. Good thermal stability was obtained.…”

Section: Pinenementioning

confidence: 99%

Sustainable cycloaliphatic polyurethanes: from synthesis to applications

Mouren

Avérous

2023

Chem. Soc. Rev.

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“…Because of the high reactivity of p-menthane-1,8-diol monohydrate, it has been used widely in the synthesis of terpene derivated medicines and pesticides. Kovals'skaya 15 and coworkers synthesized N,N'-diacyl-p-menthane-l,8-diamines via the interaction of p-menthane-1,8-diol monohydrate with various nitriles under the conditions of the Ritter reaction (scheme 6). The spatial structure of the reaction products was confirmed and a mixture of isomeric cis-and trans -N, N'-diacyl-pmethane-l,8-diamines in a ratio of 1:4 could be obtained.…”

Section: Preparation Of P-menthane-18-diol Monohydrate From Terpenesmentioning

confidence: 99%