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Journal articles on the topic 'Trisubstituted'

Author: Grafiati

Published: 5 June 2025

Last updated: 1 August 2025

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1

Mohrle, Hans, Thomas Platzek, Romanus Wille, and Detlef Wendisch. "Trisubstituted Cyclohexanes / Trisubstituted Cyclohexanes." Zeitschrift für Naturforschung B 40, no. 4 (1985): 524–33. http://dx.doi.org/10.1515/znb-1985-0415.

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C-Tertiarv vinylketones or the corresponding masked vinylketone derivatives react with pyrrolidin-2-one in the system sodium hydride.dimethylsulfoxide to substituted cyclohexanes of the 1,3.5- and sometimes additionally of the 1,2.4-type. Only acetophenone Mannich bases bearing a p-hydroxy or a dimethylamino group failed in cyclization.

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2

Arora, Pragi, Jagdeep Dua, and Jitender Singh. "Synthesis of some new 1,3,5-trisubstituted pyrazoles as antioxidant and antiinflammatory agents." Journal of Drug Delivery and Therapeutics 9, no. 2-s (2019): 343–47. http://dx.doi.org/10.22270/jddt.v9i2-s.2722.

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A series of some new 1,3,5-trisubstituted pyrazoles was synthesized by the reaction of α-β dibromochalcones with phenylhydrazine hydrochloride. α-β-Dibromochalcones were prepared by the regioselective bromination of respective chalcones with tetrabutylammonium tribromide. The synthesized trisubstituted pyrazoles were evaluated for their anti-inflammatory and antioxidant properties. Keywords: α-β-Dibromochalcones, 1,3,5-Trisubstituted pyrazoles, Tetrabutylammonium tribromide, Anti-inflammatory and antioxidant activities

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3

Morávková, Zuzana, Jiří Podešva, Valeriia Shabikova, Sabina Abbrent, and Miroslava Dušková-Smrčková. "Hydrogen Bonding of Trialkyl-Substituted Urea in Organic Environment." Molecules 30, no. 7 (2025): 1410. https://doi.org/10.3390/molecules30071410.

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Urea groups appear in many biomolecules and polymers. They have a significant impact on the properties of the materials because of their inherent strength and for their ability to participate in hydrogen bonds. Typically, in classical urea-based polymer materials, the urea groups occur in their N,N′-disubstituted state. Recently, bis-aspartates have been introduced as a novel type of hindered amine resins providing, upon crosslinking with (poly)isocyanates, the polyurea–polyaspartate thermosets (PU-ASPE) for coatings, sealants, polyelectrolytes, and other applications. These materials contain

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4

Gülten, Ş. "The Ugi Four-Component Reaction: Application in the synthesis of bis-hydantoins." Bulgarian Chemical Communications 56, no. D1 (2024): 13–18. http://dx.doi.org/10.34049/bcc.56.d.s2l4.

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Three new bis 1,3,5-trisubstituted hydantoins were synthesized by combining an Ugi four-component condensation reaction with a base induced cyclization. In the two-step sequence, first three new bis Ugi compounds were synthesized by the Ugi four-component condensation reaction, and then bis 1,3,5-trisubstituted hydantoins were obtained by intramolecular cyclization reaction.

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5

Sakhdari, Mahnaz, Ali Amoozadeh, and Eskandar Kolvari. "Magnetic nanoparticle-supported sulfonic acid as a green catalyst for the one-pot synthesis of 2,4,5-trisubstituted imidazoles and 1,2,4,5-tetrasubstituted imidazoles under solvent-free conditions." Heterocyclic Communications 27, no. 1 (2021): 71–78. http://dx.doi.org/10.1515/hc-2020-0125.

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Abstract In this work, magnetic nanoparticle-supported sulfonic acid (γ-Fe2O3-SO3H) is used as an efficient catalyst in the synthesis of 2,4,5-trisubstituted imidazoles and 1,2,4,5-tetrasubstituted imidazoles in a short time (40–70 min for trisubstituted imidazoles and 30–40 min for tetrasubstituted imidazoles) and high-purity products were obtained (92–98% for trisubstituted imidazoles and 94–98% for tetrasubstituted imidazoles) in simple multicomponent reactions. The structure of these products was confirmed via FT-IR and NMR. Green and recyclable catalysts, eco-friendly and solvent-free con

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6

Sakhdari, Mahnaz, Ali Amoozadeh, and Eskandar Kolvari. "Magnetic nanoparticle-supported sulfonic acid as a green catalyst for the one-pot synthesis of 2,4,5-trisubstituted imidazoles and 1,2,4,5-tetrasubstituted imidazoles under solvent-free conditions." Heterocyclic Communications 27, no. 1 (2021): 71–78. http://dx.doi.org/10.1515/hc-2020-0125.

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Abstract In this work, magnetic nanoparticle-supported sulfonic acid (γ-Fe2O3-SO3H) is used as an efficient catalyst in the synthesis of 2,4,5-trisubstituted imidazoles and 1,2,4,5-tetrasubstituted imidazoles in a short time (40–70 min for trisubstituted imidazoles and 30–40 min for tetrasubstituted imidazoles) and high-purity products were obtained (92–98% for trisubstituted imidazoles and 94–98% for tetrasubstituted imidazoles) in simple multicomponent reactions. The structure of these products was confirmed via FT-IR and NMR. Green and recyclable catalysts, eco-friendly and solvent-free con

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7

Sarshar, Sepehr, Chengzhi Zhang, Edmund J. Moran, et al. "2,4,5-Trisubstituted imidazoles." Bioorganic & Medicinal Chemistry Letters 10, no. 23 (2000): 2599–601. http://dx.doi.org/10.1016/s0960-894x(00)00520-5.

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8

Zhang, Chengzhi, Sepehr Sarshar, Edmund J. Moran, et al. "2,4,5-Trisubstituted imidazoles." Bioorganic & Medicinal Chemistry Letters 10, no. 23 (2000): 2603–5. http://dx.doi.org/10.1016/s0960-894x(00)00521-7.

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9

Rogers, Miriam E., and Bruce A. Averill. "Symmetrically trisubstituted triptycenes." Journal of Organic Chemistry 51, no. 17 (1986): 3308–14. http://dx.doi.org/10.1021/jo00367a011.

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10

Diederich, François, Corinne Baumgartner, and Lukas Brändli. "Synthesis of 1,2,4-Trisubstituted Imidazoles and 1,3,5-Trisubstituted 1,2,4-Triazoles." HETEROCYCLES 76, no. 1 (2008): 401. http://dx.doi.org/10.3987/com-08-s(n)21.

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11

Zhang, Zhen, Bing Shu, Yaodong Zhang, Girdhar Singh Deora, and Qing-Shan Li. "2,4,5-Trisubstituted Thiazole: A Privileged Scaffold in Drug Design and Activity Improvement." Current Topics in Medicinal Chemistry 20, no. 28 (2020): 2535–77. http://dx.doi.org/10.2174/1568026620999200917153856.

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: Thiazole is an important 5-membered heterocyclic compound containing nitrogen and sulfur atoms with various pharmaceutical applications including anti-inflammatory, anti-cancer, anti-viral, hypoglycemic, anti-bacterial and anti-fungal activities. Until now, the FDA-approved drugs containing thiazole moiety have achieved great success such as dasatinib and dabrafenib. In recent years, considerable research has been focused on thiazole derivatives, especially 2,4,5-trisubstituted thiazole derivatives, due to their multiple medicinal applications. This review covers related literature in the pa

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12

Yamada, Kohei, Naoto Kamimura, and Munetaka Kunishima. "Development of a method for the synthesis of 2,4,5-trisubstituted oxazoles composed of carboxylic acid, amino acid, and boronic acid." Beilstein Journal of Organic Chemistry 13 (July 27, 2017): 1478–85. http://dx.doi.org/10.3762/bjoc.13.146.

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A novel method for the synthesis of trisubstituted oxazoles via a one-pot oxazole synthesis/Suzuki–Miyaura coupling sequence has been developed. One-pot formation of 5-(triazinyloxy)oxazoles using carboxylic acids, amino acids and a dehydrative condensing reagent, DMT-MM, followed by Ni-catalyzed Suzuki–Miyaura coupling with boronic acids provided the corresponding 2,4,5-trisubstituted oxazoles in good yields.

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13

El-Latif Zein, Mohamed Abd, and Elsayed M. Abd El-rahim. "Synthesis and Antimicrobial Activity of some Trisubstituted Thioxoimidazolidinones." Indian Journal of Applied Research 4, no. 1 (2011): 492–95. http://dx.doi.org/10.15373/2249555x/jan2014/152.

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14

Omar, Alshazly, Abdel-Aziz Mohamed, F. A. Mohamed Mamdouh, and El-Din A. Abuo-Rahma Gamal. "Mechanisms and anticancer therapeutic potential of 1,3,4-trisubstituted pyrazole derivatives (mini review)." International Journal of Novel Research in Physics Chemistry & Mathematics 12, no. 1 (2025): 25–34. https://doi.org/10.5281/zenodo.14858508.

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<strong>Abstract:</strong> With their diverse range of biological actions, 1,3,4-trisubstituted pyrazoles have become significant compounds in medicinal chemistry, especially in the study of cancer. Since 1,3,4- trisubstituted pyrazole derivative have been demonstrated to have analgesic, anti-inflammatory, and anticancer actions, this study focuses on their pharmacological characteristics. Compounds that block cyclin-dependent kinases (CDKs) are notable examples because they cause cell cycle arrest and apoptosis in multiple cancer cell lines. Disrupting angiogenesis and tumor progression, thes

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15

Sağırlı, Akın, and Yaşar Dürüst. "Reactions of 3-(p-substituted-phenyl)-5-chloromethyl-1,2,4-oxadiazoles with KCN leading to acetonitriles and alkanes via a non-reductive decyanation pathway." Beilstein Journal of Organic Chemistry 14 (December 10, 2018): 3011–17. http://dx.doi.org/10.3762/bjoc.14.280.

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The present work describes an unfamiliar reaction of 5-(chloromethyl)-3-substituted-phenyl-1,2,4-oxadiazoles with KCN affording trisubstituted 1,2,4-oxadiazol-5-ylacetonitriles and their parent alkanes, namely, 1,2,3-trisubstituted-1,2,4-oxadiazol-5-ylpropanes. To the best of our knowledge, the current synthetic route leading to decyanated products will be the first in terms of a decyanation process which allows the transformation of trisubstituted acetonitriles into alkanes by the incorporation of KCN with the association of in situ-formed HCN and most likely through the extrusion of cyanogen

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16

Khosropour, Ahmad R. "Synthesis of 2,4,5-trisubstituted imidazoles catalyzed by [Hmim]HSO4 as a powerful Brönsted acidic ionic liquid." Canadian Journal of Chemistry 86, no. 3 (2008): 264–69. http://dx.doi.org/10.1139/v08-009.

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An efficient and green procedure for the synthesis of 2,4,5-trisubstituted imidazoles with various aldehydes using a catalytic amount of 1-methylimidazolium hydrogenesulfate as an active and low cost Brönsted acidic room temperature ionic liquid has been developed. The ionic liquid was easily separated from the reaction mixture and was recycled five times without any loss in activity.Key words: ionic liquid, 2,4,5-trisubstituted imidazoles, [Hmim]HSO4, aldehyde, benzil.

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17

Han, Gun Hee, Seo Yun Kim, Ha Rim Lee, Ji Su Lee, and Yong Sun Park. "A Convenient One-Pot Synthesis of Both Enantiomers of 1,3,5-Trisubstituted Hydantoins." Synlett 31, no. 02 (2019): 171–74. http://dx.doi.org/10.1055/s-0039-1691406.

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A novel one-pot asymmetric synthetic method for the direct conversion of bromoacetates into highly substituted hydantoins has been developed. Both enantiomers of 1,3,5-trisubstituted hydantoins were conveniently synthesized through a dynamic kinetic resolution of bromoacetates derived from either ethyl l-lactate or diacetone-d-glucose. The sequential three-component reaction permitted the preparation of (R)- or (S)-1,3,5-trisubstituted hydantoins in yields of 77–51% with enantiomeric ratios of up to 95:5.

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18

Xin, Minhang, Hui-Yan Wang, Hao Zhang, Ying Shen, and San-Qi Zhang. "Synthesis and biological activity of new 2,4,6-trisubstituted triazines as potential phosphoinositide 3-kinase inhibitors." Journal of Chemical Research 44, no. 7-8 (2020): 393–402. http://dx.doi.org/10.1177/1747519820904844.

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Twenty-five novel 2,4,6-trisubstituted triazines were synthesized and biologically evaluated. Most of the compounds synthesized showed good antiproliferative activity against HCT-116 and MCF-7. Compounds B18 and B19 showed the best antiproliferative activity. Further study showed B18 and B19 inhibited four phosphoinositide 3-kinase isoforms and mammalian target of rapamycin with good potency. These results demonstrate that 2,4,6-trisubstituted triazines are potentially useful phosphoinositide 3-kinase inhibitors for the development of new anticancer drugs.

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19

Chen, Zhao-Hua, Shi-Wei Yu, Wen-Jin Xu, et al. "Synthesis of Novel Trisubstituted Olefin-Type Probe Molecules Containing N-Heterocycles and Their Application in Detection of Malononitrile." Organics 5, no. 2 (2024): 46–58. http://dx.doi.org/10.3390/org5020004.

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Recently, the construction of the trisubstituted olefin-type probe molecules has elicited the attention of many researchers. However, the synthesis of the trisubstituted olefin-type probes containing two N-heterocycles simultaneously has been rarely reported. In this study, starting from the inexpensive mucobromic acid 1 and N-heterocyclic compound 2, we first utilized a simple one-step reaction to synthesize a series of trisubstituted olefin-type compounds 3 simultaneously bearing with the structure of two N-heterocyclic rings in the absence of transition metal catalysts with a yield of 62–86

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20

Shiri, Pezhman, Ali Mohammad Amani, and Thomas Mayer-Gall. "A recent overview on the synthesis of 1,4,5-trisubstituted 1,2,3-triazoles." Beilstein Journal of Organic Chemistry 17 (July 13, 2021): 1600–1628. http://dx.doi.org/10.3762/bjoc.17.114.

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Diverse strategies for the efficient and attractive synthesis of a wide variety of relevant 1,4,5-trisubstituted 1,2,3-triazole molecules are reported. The synthesis of this category of diverse fully functionalized 1,2,3-triazoles has become a necessary and unique research subject in modern synthetic organic key transformations in academia, pharmacy, and industry. The current review aims to cover a wide literature survey of numerous synthetic strategies. Recent reports (2017–2021) in the field of 1,4,5-trisubstituted 1,2,3-triazoles are emphasized in this current review.

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21

Neumann, William L., Karin E. Sandoval, Shirin Mobayen, et al. "Synthesis and structure–activity relationships of 3,4,5-trisubstituted-1,2,4-triazoles: high affinity and selective somatostatin receptor-4 agonists for Alzheimer's disease treatment." RSC Medicinal Chemistry 12, no. 8 (2021): 1352–65. http://dx.doi.org/10.1039/d1md00044f.

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22

Gu, Jinsong, and Xiuhui Lu. "A mechanistic study of 1,3,5-trisubstituted-1,2,3-triazoles by Ab initio method." Progress in Reaction Kinetics and Mechanism 45 (January 2020): 146867832092329. http://dx.doi.org/10.1177/1468678320923295.

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The mechanism of synthesis of 1,3,5-trisubstituted-1,2,4-triazoles from 3-thiopheneacetic acetic acid, 4-pyridine formamidine, and tri-fluoro ethyl hydrazine has been first investigated with B3LYP/6-311++G** method in this article. According to the potential energy profile, it can be predicted that the course of the reaction consists of six elementary reactions. The 3-thiopheneacetic acetic acid and 4-pyridine formamidine form first an intermediate product through a dehydration reaction; the intermediate product further combines with hydrogen ion to form a positive ions; the positive ion react

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23

Crowley, James D., Ai-Lan Lee, and Kelly J. Kilpin. "1,3,4-Trisubtituted-1,2,3-Triazol-5-ylidene 'Click' Carbene Ligands: Synthesis, Catalysis and Self-Assembly." Australian Journal of Chemistry 64, no. 8 (2011): 1118. http://dx.doi.org/10.1071/ch11185.

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This review examines the use of the Cu(I)-catalyzed 1,3-cycloaddition of organic azides with terminal alkynes (the CuAAC ‘click’ reaction) for development of a novel family of abnormal/mesoionic N-heterocyclic carbenes and their corresponding metal complexes. These 1,3,4-trisubstituted-1,2,3-triazol-5-ylidenes have donor properties that are intermediate between the traditional Arduengo-type imidazol-2-ylidenes and more highly σ-donating abnormal carbenes, such as imidazol-4-ylidenes or pyrazolin-4-ylidenes. Metal complexes of the 1,3,4-trisubstituted-1,2,3-triazol-5-ylidenes have been used as

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24

Balaji Digambar, Kokane, and S. G. Patil. "Ammonium acetate as a Dual Reagent-Catalyst Role in Efficient Synthesis of 2,4,6-Trisubstituted 1,3,5-triazines from Aldehydes." Caribbean Journal of Science and Technology 10, no. 02 (2022): 42–46. http://dx.doi.org/10.55434/cbi.2022.20106.

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The synthesis of 2,4,6-triaryl-1,3,5-triazines using iron-catalyzed cyclization of aldehydes with NH4I as the only nitrogen source is shown to be an easy, atom-efficient process. This method provides symmetrical 2,4,6-trisubstituted and unsymmetrical 1,3,5-triazines with yields ranging from 52% to 85% and operates without difficulty in an environment of air. The current methodology offers a simple and atom-efficient way for making 2,4,6-trisubstituted 1,3,5-triazines that uses an affordable, widely accessible ammonium salt as the only nitrogen source.

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25

Sun, Y., and N. Cramer. "Tailored trisubstituted chiral CpxRhIII catalysts for kinetic resolutions of phosphinic amides." Chemical Science 9, no. 11 (2018): 2981–85. http://dx.doi.org/10.1039/c7sc05411d.

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26

Gimazetdinov, A. M., V. V. Zagitov, and Z. R. Makaev. "Approaches to the Formation of the Key 2-Oxabicyclo[3.3.0]octan-3-one Precursor of Galiellalactone." Russian Journal of Organic Chemistry 60, no. 11 (2024): 2130–39. https://doi.org/10.1134/s107042802411006x.

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27

Guan, Xiao-Yu, Min Tang, Zhang-Qin Liu, and WenHao Hu. "A highly diastereoselective [5+1] annulation to 2,2,3-trisubstituted tetrahydroquinoxalines via intramolecular Mannich-type trapping of ammonium ylides." Chemical Communications 55, no. 66 (2019): 9809–12. http://dx.doi.org/10.1039/c9cc04890a.

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28

Zhang, Chun, Brandon Tutkowski, Ryan J. DeLuca, Leo A. Joyce, Olaf Wiest, and Matthew S. Sigman. "Palladium-catalyzed enantioselective Heck alkenylation of trisubstituted allylic alkenols: a redox-relay strategy to construct vicinal stereocenters." Chemical Science 8, no. 3 (2017): 2277–82. http://dx.doi.org/10.1039/c6sc04585e.

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29

Hossain, Md Imran, Md Imdadul H. Khan, Seong Jong Kim та Hoang V. Le. "Synthesis of 3,4,5-trisubstituted isoxazoles in water via a [3 + 2]-cycloaddition of nitrile oxides and 1,3-diketones, β-ketoesters, or β-ketoamides". Beilstein Journal of Organic Chemistry 18 (22 квітня 2022): 446–58. http://dx.doi.org/10.3762/bjoc.18.47.

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Herein we report a method for the synthesis of 3,4,5-trisubstituted isoxazoles in water under mild basic conditions at room temperature via a [3 + 2]-cycloaddition of nitrile oxides and 1,3-diketones, β-ketoesters, or β-ketoamides. We optimized the reaction conditions to control the selectivity of the production of isoxazoles and circumvent other competing reactions, such as O-imidoylation or hetero [3 + 2]-cycloaddition. The reaction happens fast in water and completes within 1–2 hours, which provides an environmentally friendly access to 3,4,5-trisubstituted isoxazoles, an important class of

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30

Liu, Shiqiang, Yang Zhou, Shaoguang Wu, et al. "Effect of different imidazole derived moieties on the photo- and electro-luminescence properties of 2,7,12-trisubstituted triazatruxene derivatives." New Journal of Chemistry 45, no. 45 (2021): 21395–405. http://dx.doi.org/10.1039/d1nj04487g.

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31

Minko, Yury, and Ilan Marek. "Stereodefined acyclic trisubstituted metal enolates towards the asymmetric formation of quaternary carbon stereocentres." Chem. Commun. 50, no. 84 (2014): 12597–611. http://dx.doi.org/10.1039/c4cc04391j.

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32

Jiang, Jingjing, Huawen Huang, and Guo-Jun Deng. "Four-component thiazole formation from simple chemicals under metal-free conditions." Green Chemistry 21, no. 5 (2019): 986–90. http://dx.doi.org/10.1039/c8gc03895c.

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33

Hao, Lin, Xingkuan Chen, Shaojin Chen, Ke Jiang, Jaume Torres та Yonggui Robin Chi. "Access to pyridines via DMAP-catalyzed activation of α-chloro acetic ester to react with unsaturated imines". Org. Chem. Front. 1, № 2 (2014): 148–50. http://dx.doi.org/10.1039/c3qo00045a.

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34

Divakar, Mathiyazhagan Arun, Velnathan Sudhamani, Sivakumar Shanmugam, et al. "Facile synthesis and characterization of bio-organometallic compounds and their biological activity contour against human pathogens." RSC Advances 5, no. 11 (2015): 8362–70. http://dx.doi.org/10.1039/c4ra08737b.

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35

Jeyalakshmi, Kumaramangalam, Yuvaraj Arun, Nattamai S. P. Bhuvanesh, Paramasivan Thirumalai Perumal, Anandaram Sreekanth, and Ramasamy Karvembu. "DNA/protein binding, DNA cleavage, cytotoxicity, superoxide radical scavenging and molecular docking studies of copper(ii) complexes containing N-benzyl-N′-aryl-N′′-benzoylguanidine ligands." Inorganic Chemistry Frontiers 2, no. 8 (2015): 780–98. http://dx.doi.org/10.1039/c4qi00234b.

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36

Bates, Jessica, Ashleigh L. Krider, Sana A. Malik, et al. "Synthesis and Styrene Copolymerization of Novel Chloro and Fluoro Ring-Trisubstituted Propyl Cyanophenylpropenoates." International Journal of Chemistry 11, no. 1 (2019): 79. http://dx.doi.org/10.5539/ijc.v11n1p79.

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Novel trisubstituted ethylenes, ring-substituted propyl 2-cyano-3-phenyl-2-propenoates, RPhCH=C(CN)CO2C3H7 (where R is 2,3,6-trichloro, 2,3,4-trifluoro, 2,3,5-trifluoro, 2,4,5-trifluoro, 2,4,6-trifluoro, 3,4,5-trifluoro) were prepared by the piperidine catalyzed Knoevenagel condensation of ring-trisubstituted benzaldehydes and propyl cyanoacetate.  The ethylenes when copolymerized with styrene in solution with radical initiation (ABCN) at 70&deg;C resulted in formation of copolymers. The composition of the copolymers was calculated from nitrogen analysis. The structures and pro

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37

Duong Khanh, Linh, My Hanh Trinh Thi, Thuy Quynh Bui Thi, Trung Vu Quoc, Vuong Nguyen Thien, and Luc Van Meervelt. "Synthesis, crystal structure and Hirshfeld surface analysis of 4-[3-(4-hydroxyphenyl)-4,5-dihydro-1H-pyrazol-5-yl]-2-methoxyphenol monohydrate." Acta Crystallographica Section E Crystallographic Communications 75, no. 11 (2019): 1590–94. http://dx.doi.org/10.1107/s2056989019013379.

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In the title pyrazoline derivative, C16H16N2O3·H2O, the pyrazoline ring has an envelope conformation with the substituted sp 2 C atom on the flap. The pyrazoline ring makes angles of 86.73 (12) and 13.44 (12)° with the trisubstituted and disubstituted benzene rings, respectively. In the crystal structure, the molecules are connected into chains running in the b-axis direction by O—H...N hydrogen bonding. Parallel chains interact through N—H...O hydrogen bonds and π–π stacking of the trisubstituted phenyl rings. The major contribution to the surface contacts are H...H contacts (44.3%) as conclu

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38

Kadikova, Rita, Ilfir Ramazanov, Alexey Vyatkin, and Usein Dzhemilev. "Zirconium-Catalyzed Reaction of 1-Alkynyl Sulfides with Et3Al: A Novel Route to Trisubstituted 1-Alkenyl Sulfides." Synlett 29, no. 13 (2018): 1773–75. http://dx.doi.org/10.1055/s-0037-1610431.

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The reaction of 1-alkynyl sulfides and alkynyl sulfoxides with Et3Al under zirconocene catalysis conditions has been studied. The interaction between 1-alkynyl sulfides and Et3Al in the presence of catalytic amounts of Cp2ZrCl2 leads to trisubstituted 1-alkenyl sulfides in moderate to good yields (56–73%) with high regioselectivity and stereoselectivity. 1-Alkynyl sulfoxides, upon treatment with Et3Al under the same reaction conditions, undergoes reduction to give sulfides. The excess of Et3Al (7 equiv) in this reaction causes cyclic carboalumination of in situ generated 1-alkynyl sulfide to

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39

Raguraman, A., and N. Santhi. "Synthesis and Characterization of 1,3,5-Trisubstituted Pyrazoline Derivatives by Ultrasonic Irradiation Method and Evaluation of its Antibacterial Activity." International Letters of Chemistry, Physics and Astronomy 39 (October 2014): 219–33. http://dx.doi.org/10.18052/www.scipress.com/ilcpa.39.219.

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A series of novel 1,3,5-trisubstituted pyrazoline derivatives (P1-P10) have been synthesized by the reaction of substituted chalcones (C1-C10) with 4-hydroxybenzhydrazide. The starting material, chalcones were prepared by claisen Schmidt condensation of 4-methylacetophenone with substituted aldehydes in the presence of sodium hydroxide in ethanol. 4-hydroxybenzhydrazide was synthesized by condensing methyl 4-hydroxybenzoate with hydrazine hydrate. The cycloaddition of chalcones with 4-hydroxybenzhydrazide gives 1, 3, 5-trisubstituted pyrazoline derivatives. The structures of synthesized deriva

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Lellek, Vit, Cheng-yi Chen, Wanggui Yang, Jie Liu, Xuebao Ji, and Roger Faessler. "An Efficient Synthesis of Substituted Pyrazoles from One-Pot Reaction of Ketones, Aldehydes, and Hydrazine Monohydrochloride." Synlett 29, no. 08 (2018): 1071–75. http://dx.doi.org/10.1055/s-0036-1591941.

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An efficient, one-pot and metal-free process for the preparation of 3,5-disubstituted and 3,4,5-trisubstituted pyrazoles on multi-gram scale was developed. One-pot condensation of ketones, aldehydes and hydrazine monohydrochloride readily formed pyrazoline intermediates under mild conditions. Oxidation of pyrazolines, in situ, employing bromine afforded a wide variety of pyrazoles. The methodology offers a fast, and often chromatography-free protocol for the synthesis of 3,4,5-substituted pyrazoles in good to excellent yields. Alternatively, a more benign oxidation protocol affords 3,5-disubst

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41

Raguraman, A., and N. Santhi. "Synthesis and Characterization of 1,3,5-Trisubstituted Pyrazoline Derivatives by Ultrasonic Irradiation Method and Evaluation of its Antibacterial Activity." International Letters of Chemistry, Physics and Astronomy 39 (October 2, 2014): 219–33. http://dx.doi.org/10.56431/p-10v8y4.

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Abstract:

A series of novel 1,3,5-trisubstituted pyrazoline derivatives (P1-P10) have been synthesized by the reaction of substituted chalcones (C1-C10) with 4-hydroxybenzhydrazide. The starting material, chalcones were prepared by claisen Schmidt condensation of 4-methylacetophenone with substituted aldehydes in the presence of sodium hydroxide in ethanol. 4-hydroxybenzhydrazide was synthesized by condensing methyl 4-hydroxybenzoate with hydrazine hydrate. The cycloaddition of chalcones with 4-hydroxybenzhydrazide gives 1, 3, 5-trisubstituted pyrazoline derivatives. The structures of synthesized deriva

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42

Amann, Cody D., Khushboo Khushboo, and Eike B. Bauer. "Synthesis of 2,2,5-Trisubstituted Tetrahydrofurans by Ferrocenium-Catalyzed Dehydrative Diol Cyclization Reactions." Inorganics 13, no. 2 (2025): 59. https://doi.org/10.3390/inorganics13020059.

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A ferrocenium-catalyzed synthesis of trisubstituted tetrahydrofurans by dehydrative cyclization of diols is reported. Treatment of γ-phenyl-γ-butyrolactone or valerolactone with 2–3 equivalents of MeLi, n-BuLi, or PhLi yielded the corresponding substituted 1,4-butanediols in 41–86% yields. Subsequent dehydrative cyclization of the diols under non-inert conditions using catalytic ferrocenium tetrafluoroborate (10 mol%) produced trisubstituted tetrahydrofurans in 72–83% yields after 48–72 h at 45–70 °C in CH2Cl2. This study demonstrates ferrocenium-catalyzed dehydrative cyclization for the first

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Yang, Mengchen, Chen Chen, Xing Yi, et al. "Thiosquaramide-catalysed asymmetric double Michael addition of 2-(3H)-furanones to nitroolefines." Organic & Biomolecular Chemistry 17, no. 11 (2019): 2883–86. http://dx.doi.org/10.1039/c9ob00330d.

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Wang, Li-Ya, Henry J. Tsai, Hui-Yi Lin, et al. "One-flask synthesis of 1,3,5-trisubstituted 1,2,4-triazoles from nitriles and hydrazonoyl chlorides via 1,3-dipolar cycloaddition." RSC Adv. 4, no. 27 (2014): 14215–20. http://dx.doi.org/10.1039/c4ra00113c.

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Bai, Yang, Wen Chen, Ya Chen, Huawen Huang, Fuhong Xiao та Guo-Jun Deng. "Copper-catalyzed oxidative cyclization of arylamides and β-diketones: new synthesis of 2,4,5-trisubstituted oxazoles". RSC Advances 5, № 11 (2015): 8002–5. http://dx.doi.org/10.1039/c4ra14394a.

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Dimopoulos, Paschalis, Audrey Athlan, Soraya Manaviazar, and Karl J. Hale. "On the Stereospecific Conversion of Proximally-Oxygenated Trisubstituted Vinyltriphenylstannanes into Stereodefined Trisubstituted Alkenes." Organic Letters 7, no. 24 (2005): 5373–76. http://dx.doi.org/10.1021/ol051935t.

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Sader, Jonathan K., Bryce A. Molder, and Jeremy E. Wulff. "A Chan–Evans–Lam approach to trisubstituted vinyl ethers." Organic & Biomolecular Chemistry 19, no. 44 (2021): 9649–53. http://dx.doi.org/10.1039/d1ob01827b.

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Guo, Wei. "Direct oxidative coupling of amidine hydrochlorides and methylarenes: TBHP-mediated synthesis of substituted 1,3,5-triazines under metal-free conditions." Organic & Biomolecular Chemistry 13, no. 41 (2015): 10285–89. http://dx.doi.org/10.1039/c5ob01799h.

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Jayram, Janeeka, та Vineet Jeena. "An iodine/DMSO-catalyzed sequential one-pot approach to 2,4,5-trisubstituted-1H-imidazoles from α-methylene ketones". RSC Advances 8, № 66 (2018): 37557–63. http://dx.doi.org/10.1039/c8ra07238h.

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Mandal, Debdeep, Felix Stein, Shubhadeep Chandra, et al. "Trisubstituted geminal diazaalkene derived transient 1,2-carbodications." Chemical Communications 56, no. 59 (2020): 8233–36. http://dx.doi.org/10.1039/d0cc02807j.

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