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The liquid phase of 4,4'-trimethylenedipiperidine: a safe and greener dual-task agent for clean and facile synthesis of coumarin derivatives

Gorjian H, Khaligh NG

Mol Divers, 2022 Dec;26(6):3047-3055.
PMID: 34982359 DOI: 10.1007/s11030-021-10364-7

A practical and facile synthesis of various coumarin derivatives was conducted using a liquid phase of 4,4'-trimethylenedipiperidine as a safe and greener dual-task reagent under catalyst-free and solvent-free conditions. This reagent is a commercially available solid and can be handled easily, having a liquid phase over a vast temperature range, high thermal stability, low toxicity, and good solubility in green solvents such as water and ethanol. It is worth mentioning that 4,4'-trimethylenedipiperidine could be completely recovered and regenerated after a simple process. The current method has other merits, including (a) minimizing the use of high-risk and toxic reagents and solvents; (b) the use of a secure and recoverable medium-organocatalyst instead of metal-based catalysts, (c) avoid tedious processes, harsh conditions, and a multi-step process for the preparation of catalysts, (d) transform phenol and salicyladehyde derivatives into the corresponding coumarin derivatives in good to high yields, (e) minimize hazardous waste generation. TMDP could be easily recovered and reused several times with no change in its activity. Furthermore, the current work demonstrated that the liquid phase of 4,4'-trimethylenedipiperidine can be a promising medium in organic reaction at higher temperatures due to its broad liquid range temperature, thermal stability, acceptor/donor hydrogen bond property, and other unique merits. New methodology for the synthesis of coumarines using liquid phase of TMDP under mild conditions.
Myrtle: a versatile medicinal plant

Gorjian H, Khaligh NG

Nutrire, 2023;48(1):10.
PMID: 38625264 DOI: 10.1186/s41110-023-00194-y

Myrtus, commonly called myrtle, is a genus of flowering plants in the Myrtaceae family. This study aimed to review myrtle's pharmaceutical, food, and other uses. The pharmacological effects of myrtle for antioxidant, antibacterial, and anti-inflammatory activities, reduction of COVID-19 symptoms, anti-diabetic in the animal model, hepatoprotective in the rat model, antihypertensive, control of intestinal helminthiasis in mice model, inhibition of glucosyltransferase activity, protective effect on oxidative metabolism in the hypothyroidism model, and reducing the damage caused by skin burns are reviewed. In addition, the food uses of this plant such as improving the oxidative and microbial stability of products containing salmon, antimicrobial activity in meat and dairy products, flavoring in sea salt, microbial improvement of fresh fruits during post-harvest storage, animal nutrition, and bio-oil production are summarized.
SUPPLEMENTARY INFORMATION: The online version contains supplementary material available at 10.1186/s41110-023-00194-y.
How Important is the Metal-free Catalytic Knoevenagel Reaction in Medicinal Chemistry? An Updated Review

Johari S, Johan MR, Khaligh NG

Curr Med Chem, 2024;31(27):4286-4311.
PMID: 38243980 DOI: 10.2174/0109298673260463231122074253

The Knoevenagel condensation is a powerful and primary step for the development of carbon-carbon bond transformations. These condensations offer versatile products/ intermediates for diverse uses in polymers, cosmetics, chemical industries, and medicinal chemistry. Various homogenous and heterogenous catalysts have been found to promote the Knoevenagel condensation reaction, both environmentally and economically. Due to their attractive use in the production of pharmaceutical drugs, they are proven to be the main force that drives the synthesis involving numerous multi-component and multistep reactions. The present study, therefore, aims to summarise reported Knoevenagel condensation reactions using metal-free catalysts resulting in pharmaceutically useful compounds with anti-cancer, anti-tumor, anti-oxidant, anti-malarial, anti-diabetic, and anti- bacterial activities. By considering factors like their structure-activity relationships (SARs), the reaction conditions, and the steps involved, as well as the advantages and limitations of the particular approach, we also provide a general framework and direction in order to achieve superior characteristics of the catalyst.
Application of nitrogen-rich porous organic polymer for the solid-phase synthesis of 2-amino-4H-benzo[b]pyran scaffolds using ball milling process

Zaharani L, Khaligh NG, Mihankhah T, Johan MR

Mol Divers, 2021 Feb;25(1):323-332.
PMID: 32361887 DOI: 10.1007/s11030-020-10092-4

This paper presents the efficient synthesis of 2-amino-4H-benzo[b]pyrans using mesoporous poly-melamine-formaldehyde as a polymeric heterogeneous catalyst. According to the principals of green chemistry, the reaction was performed by the planetary ball milling process at ambient and neat conditions. The heterogeneous catalyst could be reused up to five runs with no reducing of catalytic efficiency. A variety of substituted 2-amino-4H-benzo[b]pyrans were obtained in good to excellent yields under eco-friendly conditions. Other advantages of the current methodology include short reaction time, wide substrate-scope, and use of a metal-free polymeric catalyst. Also, the current method avoids the use of hazardous reagents and solvents, tedious workup and multi-step purification. This work revealed that porous organic polymers containing Lewis base sites having acceptor-donner hydrogen bonding functional groups, and high porosity could play a vital role in the promotion of the one-pot multicomponent reactions in the solid-phase synthesis.
A Green Alternative for Aryl Iodide Preparation from Aromatic Amines

Shahnavaz Z, Zaharani L, Johan MR, Khaligh NG

Curr Org Synth, 2020;17(2):131-135.
PMID: 32013833 DOI: 10.2174/1570179417666200203121437

BACKGROUND: In continuation of our previous work and the applications of saccharin, we encouraged to investigate the one-pot synthesis of the aryl iodides by the diazotization of the arene diazonium saccharin salts.
OBJECTIVE: Arene diazonium salts play an important role in organic synthesis as intermediate and a wide variety of aromatic compounds have been prepared using them. A serious drawback of arene diazonium salts is their instability in a dry state; therefore, they must be stored and handled carefully to avoid spontaneous explosion and other hazard events.
METHODS: The arene diazonium saccharin salts were prepared as active intermediates in situ through the reaction of various aryl amines with tert-butyl nitrite (TBN) in the presence of saccharin (Sac-H). Then, in situ obtained intermediates were used into the diazotization step without separation and purification in the current protocol.
RESULTS: A variety of aryl iodides were synthesized at a greener and low-cost method in the presence of TBN, Sac-H, glacial acetic acid, and TEAI.
CONCLUSION: In summary, a telescopic reaction is developed for the synthesis of aryl iodides. The current methodology is safe, cost-effective, broad substrate scope, and metal-free. All used reagents are commercially available and inert to moisture and air. Also, the saccharine and tetraethylammonium cation could be partially recovered from the reaction residue, which reduces waste generation, energy consumption, raw material, and waste disposal costs.
Surface analysis and thermal behavior of the functionalized cellulose by glutaric anhydride through a solvent-free and catalyst-free process

Fahim H, Motamedzadegan A, Farahmandfar R, Khaligh NG

Int J Biol Macromol, 2023 Mar 31;232:123268.
PMID: 36646345 DOI: 10.1016/j.ijbiomac.2023.123268

According to the 12 principles of green chemistry, surface functionalization was performed using glutaric anhydride under solvent-free and catalyst-free conditions. FTIR spectra and DS analyses demonstrated the functionalization of HCl-hydrolyzed cellulose. The influence of two parameters, i.e., the glutaric anhydride concentration and the reaction time, on the functionalization of HCl-hydrolyzed cellulose was investigated. Protocol efficiency was studied by a degree of substitution (DS). It was found that higher concentrations of glutaric anhydride cause an enhancement of DS to 0.75 and 0.87 for GA3-12 and GA9-12, respectively. In addition, the longer reaction time increased zeta potential from -12.2 ± 1.7 for G9-6 to -34.57 ± 2.2 for GA9-12. Morphology analysis by SEM showed a decrease in fiber length for the functionalized cellulose. DSC profiles confirmed dehydration at a range of 17 to 134 °C. A glass transition was revealed at -30 to -20 °C for all studied samples. The fusion, the depolymerization of cellulose chains, the cleavage of glycosidic linkages, and the decomposition of the crystalline parts of cellulose occur at 195 to 374 °C. Therefore, an efficient and greener process was developed to functionalize the HCl-hydrolyzed cellulose by glutaric anhydride, a safe and non-toxic anhydride, in the absence of the solvent and catalyst.
Fulltext Highly effective ashless and non-corrosive dimercaptobenzothiadiazole as multifunctional lubricant additives in naphthenic base oil

Ong CL, Lai YC, Heidelberg T, Tang WK, Lee VS, Khaligh NG, et al.

RSC Adv, 2023 Oct 18;13(44):30733-30742.
PMID: 37869389 DOI: 10.1039/d3ra05692a

The conventional medium chain chlorinated paraffin (MCCP) and zinc dialkyl dithiophosphate (ZDDP) additives have greatly enhanced the extreme pressure (EP) and anti-wear (AW) performance of the metalworking fluids. However, chlorine- and zinc-containing additives are restricted in use due to eco-toxicity issue. Herein, ashless and non-corrosive dimercaptobenzothiadiazole derivatives, namely bis-2,5-benzylsulfanyl-[1,3,4]thiadiazole (BBST) and bis-2,5-octylsulfanyl-[1,3,4]thiadiazole (BOST) consist of three sulfur atoms have been synthesized and evaluated. The performance of BBST shows a weld load (PD) of 3089 N and AW value of 5 mm2, which represents an improvement of 3.1 and 7.4 folds over naphthenic base oil (NBO). In addition, BBST also outperformed BOST, MCCP, and ZDDP in terms of its weld load and AW properties. Based on XPS analysis and molecular electrostatic potential maps (MEPS), BBST exhibits superior tribology performance due to the interaction between the sulfur (S), nitrogen (N), and π-electrons of the benzene ring with the metal surface. The formation of FeS, Fe2O3 and Fe⋯N coordinate bonds contributes to the creation of an excellent tribofilm.