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Multicomponent Reaction

Pooja Kumari, Ruchi Bharti, Tasneem Parvin
An efficient, mild and environmentally benign protocol has been developed for the synthesis of aminouracil-tethered tri-substituted methane derivatives. The three-component reaction of 2-hydroxy-1,4-naphthaquinone, 6-amino-1,3-dimethyluracil and aldehydes in the presence of molecular iodine as catalyst under reflux conditions resulted in aminouracil-tethered tri-substituted methane derivatives 4 in aqueous medium. Similarly, the four-component reaction of 2-hydroxy-1,4-naphthaquinone, o-phenylenediamine, aldehydes and aminouracil derivatives resulted in aminouracil-tethered tri-substituted methane derivatives 6 under the same reaction conditions...
August 14, 2018: Molecular Diversity
Pooja Purohit, Anand Kumar Pandey, Deepti Singh, Pradeep Singh Chouhan, Karthik Ramalingam, Mahendra Shukla, Neena Goyal, Jawahar Lal, Prem M S Chauhan
A series of 2,3,4,9-tetrahydro-β-carboline tetrazole derivatives ( 14a-u ) have been synthesized utilizing the Ugi multicomponent reaction and were identified as potential antileishmanial chemotypes. Most of the screened derivatives exhibited significant in vitro activity against the promastigote (IC50 from 0.59 ± 0.35 to 31 ± 1.27 μM) and intracellular amastigote forms (IC50 from 1.57 ± 0.12 to 17.6 ± 0.2 μM) of L. donovani , and their activity is comparable with standard drugs miltefosine and sodium stibogluconate...
September 1, 2017: MedChemComm
K R Soumya, Ramar Arumugam, Bhaskaran Shankar, Malaichamy Sathiyendiran
Sulfate donor based supramolecular coordination complexes [{ fac-Re(CO)3 }(μ-SO4 )(L n )2 { fac-Re(CO)3 }] (1-3) were obtained using ditopic N donors (L n ; n = 1-3), NaHSO3 , and Re2 (CO)10 in a one-pot, multicomponent, coordination-driven self-assembly approach, in which SO3 2- becomes oxidized to SO4 2- during the reaction and acts as a building framework. Complexes 1-3 were characterized using IR, ESI-TOF-MS, and 1 H NMR spectroscopy. The structures of complexes 1-3 were confirmed using single-crystal X-ray diffraction analysis...
August 14, 2018: Inorganic Chemistry
Ronak Afshari, Ahmad Shaabani
The emergence of neoteric synthetic routes for materials functionalization is an interesting phenomenon in materials chemistry. In particular, the union of materials chemistry with multicomponent reactions (MCRs) opens a new avenue leading to the realm of highly innovative functionalized architectures with unique features. MCRs have recently been recognized as considerable part of the synthetic chemist's toolbox due to their great efficiency, inherent molecular diversity, atom and pot economy along with operational simplicity...
August 14, 2018: ACS Combinatorial Science
Weiting Cai, Rentao Mu, Shenjun Zha, Guodong Sun, Sai Chen, Zhi-Jian Zhao, Hao Li, Hao Tian, Yu Tang, Franklin Feng Tao, Liang Zeng, Jinlong Gong
Progress in heterogeneous catalysis is often hampered by the difficulties of constructing active architectures and understanding reaction mechanisms at the molecular level due to the structural complexity of practical catalysts, in particular for multicomponent catalysts. Although surface science experiments and theoretical simulations help understand the detailed reaction mechanisms over model systems, the direct study of the nature of nanoparticle catalysts remains a grand challenge. This paper describes a facile construction of well-defined Pt-skin catalysts modified by different 3d transition metal (3dTM) atoms in subsurface regions...
August 2018: Science Advances
Xianwei Li, Tianzhang Wang, Yu-Jing Lu, Shaomin Ji, Yanping Huo, Bifu Liu
An oxidative cascade that involves multicomponent reaction comprising a terminal alkyne, 2-amino N-heterocycle, benzyl or allylic bromide with molecular oxygen, delivering densely functionalized imidazo fused heterocycles, is described. This reaction features a cheap catalyst, a green oxidant, and readily available starting materials, which make the overall synthesis applicable in the quick access to relevant pharmaceutical molecules with imidazole derived heterocycles.
August 9, 2018: Organic & Biomolecular Chemistry
Jing Wu, Yuanfang Kong, Lingyan Liu, Weixing Chang, Jing Li
A novel metal-free multicomponent cascade reaction was developed for the construction of thiazine imides. This four-component cascade reaction had advantages of mild reaction conditions, wide substrate scope and good atom economy. Four new bonds were formed in one pot via a 6-exo-dig iodothiolation cyclization of homopropargylic amines. The corresponding E-configurational thiazine imide products possess an exocyclic vinyliodide functional group.
August 8, 2018: Organic & Biomolecular Chemistry
Diana E Ramírez-Ornelas, Rebeca Sola-Llano, Jorge Bañuelos, Iñigo López Arbeloa, José A Martínez-Álvarez, Héctor M Mora-Montes, Bernardo Franco, Eduardo Peña-Cabrera
A series of complex boronic acids were prepared through multicomponent reactions (MCRs). Both Passerini and Ugi MCRs were carried out in which one component was an arylboronic acid. The resulting highly functionalized boronic acids participated efficiently in the Liebeskind-Srogl cross-coupling reaction with meso -methylthioBODIPY derivatives to yield complex borondipyrromethene (BODIPY) dyes in good yields. The joined spectroscopic and computational study points out the deep impact of the arylated chromophoric position on the photophysical signatures...
July 31, 2018: ACS Omega
Miao Wang, Chung-Li Dong, Yu-Cheng Huang, Yanrui Li, Shaohua Shen
Non-noble metal catalysts for high-active electrocatalytic oxygen evolution reaction (OER) are essential in large-scale application for water splitting. Herein, tricomponent metal phosphides with hollow structures are synthesized from cobalt-contained metal organic frameworks (MOFs), i.e., ZIF-67, by tailoring the feeding ratios of Ni and Fe, followed by a high-temperature reduction and a subsequent phosphidation process. Excellent OER activity and long-time stability are achieved in 1 m NaOH aqueous solution, with an overpotential of 329 mV at 10 mA cm-2 and Tafel slope of 48...
August 7, 2018: Small
Danil P Zarezin, Olga I Shmatova, Valentine G Nenajdenko
An efficient three-step synthesis of a novel family of enantiomerically pure isocyanides derived from β3-isocyanopropionic acids was elaborated. Easily available N-formylated α-amino acids were used as starting materials towards this aim. The 3-step sequence (Arndt-Eistert reaction-Wolff rearrangement-dehydration) resulted in target isonitriles in good yields (up to 97%). As a result a new family of isocyanides bearing a fragment of β3-amino acids with different functional groups (amides, esters and short peptides) was obtained...
August 7, 2018: Organic & Biomolecular Chemistry
Iqbal Ahmad, Tania Mirza, Zubair Anwar, Muhammad Ahsan Ejaz, Muhammad Ali Sheraz, Sofia Ahmed
A multicomponent spectrofluorimetric method has been developed for the simultaneous assay of formylmethylflavin (FMF), an intermediate product in the photolysis of riboflavin (vitamin B2 ), and its side-chain hydrolytic products, lumichrome (LC) in acidic solution and LC and lumiflavin (LF) in the alkaline solution as well as its ring cleavage products, 1,2-dihydro-1-methyl-2-keto-3-quinoxaline carboxylic acid (KA) and 1,2,3,4-tetrahydro-1-methyl-2,3-dioxo-quinoxaline (DQ) in alkaline solution. The assay method also takes into account an oxidation product of FMF, i...
July 25, 2018: Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy
Hengtuo Yang, Jiawei Guo, Ziwei Gao, Jing Gou, Binxun Yu
A novel stereospecific synthesis of ( Z)- and ( E)-β-triazole-acrylates by the combined use of a multicomponent reaction and photocatalyst-free photoisomerization is presented. The former can be regarded as a furfuryl cation induced formal [3 + 2]-cycloaddition/ring-opening/esterification domino sequence, which provides fast access to a variety of structurally diverse ( Z)-β-triazole-acrylates. The products were further photoisomerized to ( E)-configuration by UV irradiation. This efficient strategy was utilized in the concise synthesis of histone deacetylase inhibtor NSC746457 in high yield...
August 1, 2018: Organic Letters
Dong Zhang, Lili Lin, Jian Yang, Xiaohua Liu, Xiaoming Feng
Highly enantioselective synthesis of tetrahydroindolizines via catalytic multicomponent cycloaddition reactions of diazoacetate, pyridine, and alkenyloxindole was developed. Under the relay catalysis involving an achiral iron(III) catalyst and chiral N,N'-dioxide-scandium(III) complex, a series of tetrahydroindolizines bearing different substituents were obtained in moderate to high yields (up to 99%) with excellent diastereo- and enantioselectivities (up to >19:1 d.r., 99% ee).
July 31, 2018: Angewandte Chemie
Ze Zhang, Yezi You, Chunyan Hong
Control over the monomer sequence during polymerization has attracted great attention in polymer science, but it remains a serious challenge. Recently, multicomponent reactions have been playing a significant role in the synthesis of sequence-controlled polymers due to their inherent advantage of combining three or more starting materials in time-saving, one-pot operations to afford complex microstructures. In this feature article, the recent representative developments in the synthesis of sequence-controlled polymers by multicomponent reactions are highlighted to give insight on the design of novel sequence-controlled polymers with sufficient molecular diversity and complexity...
July 31, 2018: Macromolecular Rapid Communications
Zheng Chang, Yue Yang, Jie He, James F Rusling
Gold (Au) is chemically stable and resistant to oxidation. Although bulk Au is catalytically inert, nanostructured Au exhibits unique size-dependent catalytic activity. When Au nanocatalysts are supported on conductive carbon (denoted as Au@C), Au@C becomes promising for a wide range of electrochemical reactions such as electrooxidation of alcohols and electroreduction of carbon dioxide. In this mini-review, we summarize Au@C nanocatalysts with specific attention on the most recent achievements including the findings in our own laboratories, and show that Au nanoclusters (AuNCs, <2 nm) on nitrided carbon are excellent electrocatalysts for the oxidation of organic molecules including guanines in DNA...
August 1, 2018: Dalton Transactions: An International Journal of Inorganic Chemistry
Raju S Thombal, Yong Rok Lee
Indium(III)/silver(I)-catalyzed [2 + 2 + 1] annulation of arylhydrazine hydrochlorides with β-enamino esters via multicomponent reactions for the construction of diverse and multisubstituted N-arylpyrazoles has been demonstrated. The oxidative cycloaddition proceeds via a cascade triple Michael addition/elimination/air oxidation. This novel protocol provides a rapid and efficient synthetic route to various 3,4-diester-substituted N-arylpyrazoles. The synthesized compounds are further utilized for various synthetic transformations...
August 3, 2018: Organic Letters
A A Kamalov, A M Takhirzade
AIM: To investigate the efficacy and safety of various medical treatment schemes in the management of patients at high risk of progression of benign prostatic hyperplasia (BPH), depending on concomitant erectile dysfunction (ED). MATERIALS AND METHODS: The study comprised 247 men with an I-PSS score of 8 or more, a prostate volume of more than 40 cm3, and a prostate specific antigen level of 1.5-4.0 ng/ml. Patients were divided into 2 groups: group 1 included patients without ED (IIEF-5 score >21); patients of group 2 had ED (IIEF-5 score less or equal 21)...
July 2018: Urologii︠a︡
R L Greenaway, V Santolini, M J Bennison, B M Alston, C J Pugh, M A Little, M Miklitz, E G B Eden-Rump, R Clowes, A Shakil, H J Cuthbertson, H Armstrong, M E Briggs, K E Jelfs, A I Cooper
Supramolecular synthesis is a powerful strategy for assembling complex molecules, but to do this by targeted design is challenging. This is because multicomponent assembly reactions have the potential to form a wide variety of products. High-throughput screening can explore a broad synthetic space, but this is inefficient and inelegant when applied blindly. Here we fuse computation with robotic synthesis to create a hybrid discovery workflow for discovering new organic cage molecules, and by extension, other supramolecular systems...
July 20, 2018: Nature Communications
Reza Aryan, Hamid Beyzaei, Masoomeh Nojavan, Fatemeh Pirani, Hojat Samareh Delarami, Mahmood Sanchooli
A facile and efficient catalyst- and oxidant-free multicomponent synthesis of a small library of highly substituted pyrido[2,3-d]pyrimidine derivatives is reported. The products were obtained within relatively short reaction times in good to excellent yields in the presence of deep eutectic solvents as media and promoters. Simple purification and reusability of the deep eutectic solvent were the other beneficial factors of the reported protocol. All of the synthesized derivatives were thoroughly screened for possible in vitro antibacterial and antifungal effects against twenty-two bacterial and three fungal pathogens...
July 19, 2018: Molecular Diversity
Lan-Gui Xie, Darren J Dixon
Amides are ubiquitous in the fine chemical, agrochemical and pharmaceutical industries, but are rarely exploited as substrates for homologous amine synthesis. By virtue of their high chemical stability, they are essentially inert to all but the harshest of chemical reagents and to the majority of chemical transformations routinely used in organic synthesis. Accordingly, the development of chemoselective carbon-carbon bond-forming methodologies arising from the functionalization of the amide functionality should find widespread use across academia and industry...
July 19, 2018: Nature Communications
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