Chemistry of Essential Oils
K. Hüsnü Can Başer, Gerhard Buchbauer in Handbook of Essential Oils, 2020
Oxidation of toluene (181) with air or oxygen in the presence of a catalyst gives benzyl alcohol (194), benzaldehyde (195), or benzoic acid (196) depending on the chemistry employed. The demand for benzoic acid far exceeds that for the other two oxidation products and so such processes are usually designed to produce mostly benzoic acid with benzaldehyde as a minor product. For the fragrance industry, benzoic acid is the precursor for the various benzoates of interest, while benzaldehyde, through aldol-type chemistry, serves as the key intermediate for cinnamate esters (such as methyl cinnamate (197)) and cinnamaldehyde (48). Reduction of the latter gives cinnamyl alcohol (49) and hence, through esterification, provides routes to all of the cinnamyl esters. Chlorination of toluene under radical conditions gives benzyl chloride (198). Hydrolysis of the chloride gives benzyl alcohol (194), which can, in principle, be esterified to give the various benzyl esters (199) of interest. However, these are more easily accessible directly from the chloride by reaction with the sodium salt of the corresponding carboxylic acid. All of these conversions are shown in Figure 6.33.
Licit and illicit drugs
Jason Payne-James, Richard Jones in Simpson's Forensic Medicine, 2019
Many of these newly abused drugs belong to the chemical class known as piperazines, derived from piperazine and benzyl chloride. Piperazines were originally used as worming agents in humans and in veterinary medicine, particularly in the treatment of round worms (especially Ascaris); they paralyse the worms so they are flushed out by peristalsis. However, the medicinal use of piperazines is banned in many countries. Ironically, more than half of the cocaine sold in the USA is contaminated with levamisole, a piperazine anti-helminthic drug, which was initially withdrawn from the US market because it is known to induce bone marrow suppression. Several piperazines derivatives are now in circulation.
An Overview of Helminthiasis
Venkatesan Jayaprakash, Daniele Castagnolo, Yusuf Özkay in Medicinal Chemistry of Neglected and Tropical Diseases, 2019
Bephenium (14) is a quaternary ammonium derivative effective in the treatment of ascariasis, ankylostomiasis, enterobiasis, trichostrongyliasis and tricocefalosis. It is a cholinergic agonist resulting in paralysis of the parasite musculature. For the synthesis of bephenium, sodium phenolate and 2-dimethylaminoethylchloride are first reacted to give N-(2-phenoxyethyl)dimethylamine which is then treated with benzyl chloride. The resulting ammonium compound is reacted with the sodium salt of 3-hydroxy-2-naphthoic acid to afford bephenium (Vardanyan and Hruby 2006).
Synthesis, biological evaluation and molecular docking investigation of new sulphonamide derivatives bearing naphthalene moiety as potent tubulin polymerisation inhibitors
Published in Journal of Enzyme Inhibition and Medicinal Chemistry, 2021
Guangcheng Wang, Meiyan Fan, Wenjing Liu, Min He, Yongjun Li, Zhiyun Peng
The sulphonamide derivatives (5a-5e and 8a-8i) were synthesised according to the synthetic route illustrated in Scheme 1. Firstly, 3,4,5-trimethoxyaniline 1 was condensed with 4-methoxybenzoyl chloride 2 in the presence of Et3N as base at room temperature to afford intermediate 3 in high yields, followed by the carbonyl reduction reaction with LiAlH4 to give the key intermediate 4[27]. Then, condensation of compound 4 with appropriate commercially available aryl sulphonyl chloride in the presence of Et3N and DMAP in THF to generate the title compounds (5a-5e) in high yields. On the other hand, treatment of 3,4,5-trimethoxyaniline 1 with naphthalene-1-sulphonyl chloride 6 in the presence of Et3N in CH2Cl2 to afforded key intermediate 7, which reacted with commercially available benzyl halide in the presence of KI and K2CO3 to provide the title compounds (8a-8i). All target derivatives were fully characterised by 1H NMR, 13 C NMR, HRMS, and elemental analysis (see Supporting Information).
Benzimidazole derivatives endowed with potent antileishmanial activity
Published in Journal of Enzyme Inhibition and Medicinal Chemistry, 2018
Michele Tonelli, Elena Gabriele, Francesca Piazza, Nicoletta Basilico, Silvia Parapini, Bruno Tasso, Roberta Loddo, Fabio Sparatore, Anna Sparatore
The treatment of the 1-unsubstituted benzimidazoles with excess of methyl iodide, in the presence of anhydrous K2CO3, gave place to mixtures of 1-methyl-2-substituted benzimidazoles (2, 7 and 19) and 1,3-dimethyl-2-substituted benzimidazolium iodides (3, 8 and 20) (Schemes 1 and 4). The dimethylated compounds were easily isolated being insoluble in dry ether, while the monomethylated compounds were separated from the N-unsubstituted benzimidazoles by CC on silica, eluting with CH2Cl2. Similarly, by treating compounds 1 and 6 with an excess of benzyl chloride the 1,3-dibenzyl benzimidazolium chlorides 5 and 15 were obtained, but the mono-benzylated compound (13) was isolated only in the case of 6 (Scheme 1). Compounds 2, 3 and 8 were already described (see Materials and methods).
Synthesis, pharmacology and molecular docking on multifunctional tacrine-ferulic acid hybrids as cholinesterase inhibitors against Alzheimer’s disease
Published in Journal of Enzyme Inhibition and Medicinal Chemistry, 2018
Jie Zhu, Hongyu Yang, Yao Chen, Hongzhi Lin, Qi Li, Jun Mo, Yaoyao Bian, Yuqiong Pei, Haopeng Sun
The preparation of the target compounds started from methyl 2-aminobenzoate1 through seven steps as described in Scheme 1 methyl 2-aminobenzoate1 was hydrolysed to yield 2-aminobenzoic acid2, which is condensed with cyclohexanone to give 9-chloro-1,2,3,4-tetrahydroacridine3. N1–(1,2,3,4-tetrahydroacridin-9-yl)ethane-1,2-diamine4 was obtained by aminolysis of 9-chloro-1,2,3,4-tetrahydroacridine with ethane-1,2-diamine. Compound 5 was substituted with benzyl bromide or benzyl chloride, followed by the hydrolysis of ester group to form compound 8a–8m. Then, the hydrolysates were treated with thionyl chloride to prepare the corresponding chlorides, which were condensed with compound 4 to afford target compounds 10a–10m.
Related Knowledge Centers
- Organic Compound
- Phenyl Group
- Toluene
- Chemical Formula
- Organochlorine Chemistry
- Building Block
- Organic Photochemistry
- Chlorine
- Benzal Chloride
- Benzotrichloride