Synthesis of pyrrolidinedione-fused hexahydropyrrolo[2,1-a]isoquinolines via three-component [3 + 2] cycloaddition followed by one-pot N-allylation and intramolecular Heck reactions

• Xiaoming Ma,
• Suzhi Meng,
• Xiaofeng Zhang,
• Qiang Zhang,
• Shenghu Yan,
• Yue Zhang and
• Wei Zhang

Beilstein J. Org. Chem. 2020, 16, 1225–1233, doi:10.3762/bjoc.16.106

• ]isoquinolines. The multicomponent reaction was combined with one-pot reactions to make a synthetic method with good pot, atom and step economy. MeCN was used as a preferable green solvent for the reactions. Keywords: [3 + 2] cycloaddition; Heck reaction; hexahydropyrrolo[2,1-a]isoquinoline; one-pot reactions

• via sequential 1,3-dipolar cycloaddition, N-allylation, and intramolecular Heck cyclization reactions [50][51][52][53][54] (Scheme 2, K). Both stabilized and non-stabilized azomethine ylides could be used for the initial [3 + 2] cycloaddition. A multicomponent reaction was combined with one-pot

Fluorinated phenylalanines: synthesis and pharmaceutical applications

• Laila F. Awad and
• Mohammed Salah Ayoup

Beilstein J. Org. Chem. 2020, 16, 1022–1050, doi:10.3762/bjoc.16.91

• 53a–h [48]. The free amino acid 53i was prepared by the same protocol [49] (Scheme 12). 2,5-Difluorophenylalanines with either R or S configuration were synthesized also via the Erlenmeyer azalactone method. The synthesis started with the multicomponent reaction of aldehyde 55, acetylglycine 51a and

Asymmetric synthesis of CF₂-functionalized aziridines by combined strong Brønsted acid catalysis

• Xing-Fa Tan,
• Fa-Guang Zhang and
• Jun-An Ma

Beilstein J. Org. Chem. 2020, 16, 638–644, doi:10.3762/bjoc.16.60

• Tianjin University, Fuzhou 350207, China 10.3762/bjoc.16.60 Abstract A diastereo- and enantioselective approach to access chiral CF2-functionalized aziridines from difluorodiazoethyl phenyl sulfone (PhSO2CF2CHN2) and in situ-formed aldimines is described. This multicomponent reaction is enabled by a

A systematic review on silica-, carbon-, and magnetic materials-supported copper species as efficient heterogeneous nanocatalysts in “click” reactions

• Pezhman Shiri and
• Jasem Aboonajmi

Beilstein J. Org. Chem. 2020, 16, 551–586, doi:10.3762/bjoc.16.52

Ultrasonic-assisted unusual four-component synthesis of 7-azolylamino-4,5,6,7-tetrahydroazolo[1,5-a]pyrimidines

• Yana I. Sakhno,
• Maryna V. Murlykina,
• Oleksandr I. Zbruyev,
• Anton V. Kozyryev,
• Svetlana V. Shishkina,
• Dmytro Sysoiev,
• Vladimir I. Musatov,
• Sergey M. Desenko and
• Valentyn A. Chebanov

Beilstein J. Org. Chem. 2020, 16, 281–289, doi:10.3762/bjoc.16.27

• 7-azolylaminotetrahydroazolo[1,5-a]pyrimidines. Keywords: 5-amino-1H-pyrazole-4-carbonitrile; 3-amino-1,2,4-triazole; 7-azolylaminotetrahydroazolo[1,5-a]pyrimidines; heterocycle; multicomponent reaction; ultrasonication; Introduction Tetrahydropyrimidines are heterocycles of high pharmacological

• (Figure 3). Conclusion In this study we disclosed a new direction for the multicomponent reaction of 5-aminopyrazole-4-carbonitriles or 3-amino-1,2,4-triazole with pyruvic acid or ethyl pyruvate and aromatic aldehydes under ultrasonication, leading to 7-azolylamino-4,5,6,7-tetrahydroazolo[1,5-a

Combining the Ugi-azide multicomponent reaction and rhodium(III)-catalyzed annulation for the synthesis of tetrazole-isoquinolone/pyridone hybrids

• Gerardo M. Ojeda,
• Prabhat Ranjan,
• Pavel Fedoseev,
• Lisandra Amable,
• Upendra K. Sharma,
• Daniel G. Rivera and
• Erik V. Van der Eycken

Beilstein J. Org. Chem. 2019, 15, 2447–2457, doi:10.3762/bjoc.15.237

• . Keywords: C–H activation; cyclization; isoquinolone; multicomponent reaction; tetrazole; Introduction Pyridones and isoquinolones are relevant heterocyclic scaffolds present in numerous bioactive compounds and natural products [1][2][3][4]. Similarly, molecules containing a tetrazole ring exhibit a wide

Vicinal difunctionalization of alkenes by four-component radical cascade reaction of xanthogenates, alkenes, CO, and sulfonyl oxime ethers

• Shuhei Sumino,
• Takahide Fukuyama,
• Mika Sasano,
• Ilhyong Ryu,
• Antoine Jacquet,
• Frédéric Robert and
• Yannick Landais

Beilstein J. Org. Chem. 2019, 15, 1822–1828, doi:10.3762/bjoc.15.176

• functionalities, have the potential for further elaboration. Keywords: CO; multicomponent reaction; radicals; sulfonyl oxime ethers; xanthogenates; Introduction Multicomponent reactions constitute a powerful and highly efficient tool in organic synthesis to build up intricate compounds from simple molecules in

• /acceptor type C1 synthons [6][7][8][9][10][11][12][13][14][15]. In this context, sulfonyl oxime ethers are powerful acceptors of type C1 synthon [8][16][17], which terminates the multicomponent reaction by a β-scission of RSO2 radicals [18][19][20]. Recently, one of us reported on a three-component radical

A novel three-component reaction between isocyanides, alcohols or thiols and elemental sulfur: a mild, catalyst-free approach towards O-thiocarbamates and dithiocarbamates

• András György Németh,
• György Miklós Keserű and
• Péter Ábrányi-Balogh

Beilstein J. Org. Chem. 2019, 15, 1523–1533, doi:10.3762/bjoc.15.155

• Andras Gyorgy Nemeth Gyorgy Miklos Keseru Peter Abranyi-Balogh Hungarian Academy of Sciences, Research Centre for Natural Sciences, Institute of Organic Chemistry, Medicinal Chemistry Research Group, 1519 Budapest, POB 286, Hungary 10.3762/bjoc.15.155 Abstract A new multicomponent reaction has

• ; multicomponent reaction; one-pot; thiocarbamate; Introduction O-Thiocarbamates belong to a class of important biologically active molecules, used mainly as fungicides [1][2][3] in agricultural and pharmaceutical fields. In particular, recently antitumor [4], anesthetic [5] and enzyme inhibitory effects were

• the work-up, no chromatography was necessary and the crude product was purified by recrystallization from hexane/ethyl acetate. The three collected crops of crystals provided the thiocarbamate 3a in a total of 74% yield. We have envisaged that our multicomponent reaction could be compatible with

A heteroditopic macrocycle as organocatalytic nanoreactor for pyrroloacridinone synthesis in water

• Piyali Sarkar,
• Sayan Sarkar and
• Pradyut Ghosh

Beilstein J. Org. Chem. 2019, 15, 1505–1514, doi:10.3762/bjoc.15.152

• nanoreactor which is a single molecule as catalyst in the earliest steps of the mechanistic pathway (Figure 6). This multicomponent reaction is expected to comprise a series of condensations and subsequent ring-closure cascade reactions (Scheme 3). To demonstrate the mechanistic pathway, dimedone (2), isatin

Efficiency Eff_syn of complex syntheses as multicomponent reactions, its algorithm and calculations based on concrete criteria

• Heiner Eckert

Beilstein J. Org. Chem. 2019, 15, 1425–1433, doi:10.3762/bjoc.15.142

• synthesis steps yn (Equation 1). An extreme example for the impact of the overall yield is the tropinone synthesis by Willstätter (yoa = 0.75%) [7][8] compared to the Robinson–Schöpf synthesis (yoa = 90%) [9][10]) using a double Mannich reaction, a multicomponent reaction (MCR) [11][12][13]. The Mannich-3CR

Doebner-type pyrazolopyridine carboxylic acids in an Ugi four-component reaction

• Maryna V. Murlykina,
• Oleksandr V. Kolomiets,
• Maryna M. Kornet,
• Yana I. Sakhno,
• Sergey M. Desenko,
• Victoriya V. Dyakonenko,
• Svetlana V. Shishkina,
• Oleksandr A. Brazhko,
• Vladimir I. Musatov,
• Alexander V. Tsygankov,
• Erik V. Van der Eycken and
• Valentyn A. Chebanov

Beilstein J. Org. Chem. 2019, 15, 1281–1288, doi:10.3762/bjoc.15.126

• , Kharkiv, Ukraine Peoples' Friendship University of Russia, Miklukho-Maklya str., 6, 117198, Moscow, Russia 10.3762/bjoc.15.126 Abstract Substituted 1H-pyrazolo[3,4-b]pyridine-4- and 1H-pyrazolo[3,4-b]pyridine-6-carboxamides have been synthetized through a Doebner–Ugi multicomponent reaction sequence in a

Multicomponent reactions (MCRs): a useful access to the synthesis of benzo-fused γ-lactams

• Edorta Martínez de Marigorta,
• Jesús M. de Los Santos,
• Ana M. Ochoa de Retana,
• Javier Vicario and
• Francisco Palacios

Beilstein J. Org. Chem. 2019, 15, 1065–1085, doi:10.3762/bjoc.15.104

• dialkyl ones (Scheme 26, path A) [104]. When cyclopropyl ketones 91 were used as substrates, a ring expansion and a new quaternary centre formation happened through the multicomponent reaction to produce pentacyclic derivatives 92 (Scheme 26, path B) [105]. These reactions, either with arenes 86 or

• . Another aromatic aldehyde, in this case derived from a quinoline, can also be used as substrate for a multicomponent reaction, appropriate for the preparation of 3-aminoisoindolinone analogues 98 (Scheme 28) [106]. Indeed, the reaction of chloroquinolinecarbaldehydes 97 with isocyanides 42 and aromatic

• -(2-iodoaryl)acrylamides 113, DABCO·(SO2)2 (69) and hydrazines 114. Proposed mechanism for the preparation of oxindoles 115. Three-component reaction of acrylamide 113, CO (23) and 1,4-benzodiazepine 121. Multicomponent reaction of sulfonylacrylamides 123, aryldiazonium tetrafluoroborates 68 and DABCO

Mechanochemistry of supramolecules

• Anima Bose and
• Prasenjit Mal

Beilstein J. Org. Chem. 2019, 15, 881–900, doi:10.3762/bjoc.15.86

• -component [Fe(CD3)]2+ 28. a) Subcomponent synthesis of catalyst and reagent and b) followed by multicomponent reaction for synthesis of dihydropyrimidones. A dynamic combinatorial library (DCL) could be self-sorted to two distinct products. Mechanochemical synthesis of dynamic covalent systems via

Efficient synthesis of pyrazolopyridines containing a chromane backbone through domino reaction

• Razieh Navari,
• Saeed Balalaie,
• Saber Mehrparvar,
• Fatemeh Darvish,
• Frank Rominger,
• Fatima Hamdan and
• Sattar Mirzaie

Beilstein J. Org. Chem. 2019, 15, 874–880, doi:10.3762/bjoc.15.85

• (1.2 mmol), malononitile (1.2 mmol), Et3N (40 mmol %) in 3 mL ethanol at room temperature for 8–12 h. Structures of synthesized compounds 5a–d. Synthesis of pyrazolopyridines containing chromone 4a–m through a multicomponent reaction. The proposed mechanism for the synthesis of pyrazolopyridines

Thiol-free chemoenzymatic synthesis of β-ketosulfides

• Adrián A. Heredia,
• Martín G. López-Vidal,
• Marcela Kurina-Sanz,
• Fabricio R. Bisogno and
• Alicia B. Peñéñory

Beilstein J. Org. Chem. 2019, 15, 378–387, doi:10.3762/bjoc.15.34

• Orgánica, Facultad de Química, Bioquímica y Farmacia, UNSL. Chacabuco y Pedernera, San Luis, 5700, Argentina 10.3762/bjoc.15.34 Abstract A preparation of β-ketosulfides avoiding the use of thiols is described. The combination of a multicomponent reaction and a lipase-catalysed hydrolysis has been

Mn-mediated sequential three-component domino Knoevenagel/cyclization/Michael addition/oxidative cyclization reaction towards annulated imidazo[1,2-a]pyridines

• Olga A. Storozhenko,
• Alexey A. Festa,
• Delphine R. Bella Ndoutoume,
• Alexander V. Aksenov,
• Alexey V. Varlamov and
• Leonid G. Voskressensky

Beilstein J. Org. Chem. 2018, 14, 3078–3087, doi:10.3762/bjoc.14.287

• proceeds through a domino Knoevenagel/cyclization/Michael addition/oxidative cyclization reaction sequence. Keywords: 2-aminochromene; domino reaction; imidazo[1,2-a]pyridine; 2-iminochromene; Michael addition; multicomponent reaction; oxidation; pyridine amination; Introduction Domino reactions are well

Molecular iodine-catalyzed one-pot multicomponent synthesis of 5-amino-4-(arylselanyl)-1H-pyrazoles

• Camila S. Pires,
• Daniela H. de Oliveira,
• Maria R. B. Pontel,
• Jean C. Kazmierczak,
• Roberta Cargnelutti,
• Diego Alves,
• Raquel G. Jacob and
• Ricardo F. Schumacher

Beilstein J. Org. Chem. 2018, 14, 2789–2798, doi:10.3762/bjoc.14.256

• de Santa Maria – UFSM, 97105-900, Santa Maria, RS, Brazil 10.3762/bjoc.14.256 Abstract A one-pot iodine-catalyzed multicomponent reaction has been developed for the selective preparation of 5-amino-4-(arylselanyl)-1H-pyrazoles from a diverse array of benzoylacetonitriles, arylhydrazines and diaryl

• -(phenylselanyl)-1H-pyrazol-5-amine was submitted to an oxidative dehydrogenative coupling to produce a diazo compound confirmed by X-ray analysis. Keywords: diaryl diselenide; diazo compound; 1H-pyrazole; molecular iodine; multicomponent reaction; Introduction Selenium-containing compounds are of great

• . Molecular structure of compound 6. The hydrogen atoms are omitted for clarity [27]. Synthesis of selanyl-pyrazoles and their derivatives previously described. Multicomponent reaction proposed in this work. Direct selanylation reaction of 5-amino-pyrazole 5a with diphenyl diselenide (3a) under the optimized

An overview on recent advances in the synthesis of sulfonated organic materials, sulfonated silica materials, and sulfonated carbon materials and their catalytic applications in chemical processes

• Hashem Sharghi,
• Pezhman Shiri and
• Mahdi Aberi

Beilstein J. Org. Chem. 2018, 14, 2745–2770, doi:10.3762/bjoc.14.253

• homogeneous conditions (Scheme 5). After this successful application, catalyst 31 was tested in the synthesis of bis(2-amino-4H-pyran) derivatives 39–44 via a one-pot multicomponent reaction of dialdehydes 38 (instead of isatin and acenaphthenequinone substrates), a variety of C–H activated acids 20a,b, 23

Assembly of fully substituted triazolochromenes via a novel multicomponent reaction or mechanochemical synthesis

• Robby Vroemans,
• Yenthel Verhaegen,
• My Tran Thi Dieu and
• Wim Dehaen

Beilstein J. Org. Chem. 2018, 14, 2689–2697, doi:10.3762/bjoc.14.246

• was carried out for several salicylaldehydes and gave a clear improvement in the yield of the corresponding triazolochromenes and consequently showed to be a viable alternative for solid salicylaldehydes. Keywords: ball milling; multicomponent reaction; 3-nitro-2H-chromene; one-pot synthesis; 1,2,3

Design, synthesis and structure of novel G-2 melamine-based dendrimers incorporating 4-(n-octyloxy)aniline as a peripheral unit

• Cristina Morar,
• Pedro Lameiras,
• Attila Bende,
• Gabriel Katona,
• Emese Gál and
• Mircea Darabantu

Beilstein J. Org. Chem. 2018, 14, 1704–1722, doi:10.3762/bjoc.14.145

• disappointment, the attempted O,O’-bis-alkylation of 1 with 1-iodooctane (Williamson etherification, Table 1, entry 1), afforded a multicomponent reaction mixture (TLC monitoring, 100% conversion of 1), from which we succeeded in isolating only G-0 chloro-dendron 2a and the O,O’,N-tris-alkylated side product 2b

Hypervalent organoiodine compounds: from reagents to valuable building blocks in synthesis

• Gwendal Grelier,
• Benjamin Darses and
• Philippe Dauban

Beilstein J. Org. Chem. 2018, 14, 1508–1528, doi:10.3762/bjoc.14.128

• ligands, and tolerates a variety of substituents on both the indole and the iodonium salt. However, the atom-economy of the reaction is limited by the need to use the iodonium salts in slight excess (1.5 equivalents). Another multicomponent reaction has been designed for the preparation of

5-Aminopyrazole as precursor in design and synthesis of fused pyrazoloazines

• Ranjana Aggarwal and
• Suresh Kumar

Beilstein J. Org. Chem. 2018, 14, 203–242, doi:10.3762/bjoc.14.15

• described the construction of spiro[indoline-3,4'-pyrazolo[3,4-b]pyridine] derivatives 57 from the multicomponent reaction of 5-amino-3-hydroxy-1-phenyl-1H-pyrazole (46), ketones 56 and isatin 54 in water/acetic acid (3:1) at 90 °C (Scheme 12). Quiroga et al. [58] reported the synthesis of the pyrazolo[3,4

• first direct conversion of acenaphthenequinone to a naphthoic acid fragment via C–C bond cleavage in a single step. Recently, D. Anand et al. [63] have reported the synthesis of pyrazolo[3,4-b]pyridine derivatives 71 and 72 through the multicomponent reaction of 1-aryl-3-indolyl-5-aminopyrazoles 16

• -aminopyrazole 16, arylaldehyde 47, and 2H-thiopyran-3,5(4H,6H)-dione (79) in glacial acetic acid in presence of ammonium acetate (Scheme 20). The multicomponent reaction of 5-amino-3-hydroxypyrazoles 82, substituted salicylic aldehydes 83 and acetylacetic ester 81 in acetic acid with few drops of piperidine was

Consecutive hydrazino-Ugi-azide reactions: synthesis of acylhydrazines bearing 1,5-disubstituted tetrazoles

• Angélica de Fátima S. Barreto,
• Veronica Alves dos Santos and
• Carlos Kleber Z. Andrade

Beilstein J. Org. Chem. 2017, 13, 2596–2602, doi:10.3762/bjoc.13.256

• tetrazoles are intermolecular cycloaddition reactions and isocyanide-based multicomponent reactions (IMCRs). Indeed, the Ugi-multicomponent reaction using TMSN3 (trimethylsilyl azide) as acid component, originally reported by Ugi in 1961 [10], is one of the best and most general methods for the synthesis of

• and 6 with hydrazine monohydrate, following a known procedure (Scheme 2) [31]. To access the acylhydrazino-tetrazoles, the hydrazides 2a–c were subjected to a multicomponent reaction comprising an aldehyde or ketone 7a–h, trimethylsilyl azide (TMSN3, 8), methyl isocyanoacetate (9) and ZnCl2 (10 mol

One-pot three-component route for the synthesis of S-trifluoromethyl dithiocarbamates using Togni’s reagent

• Azim Ziyaei Halimehjani,
• Martin Dračínský and
• Petr Beier

Beilstein J. Org. Chem. 2017, 13, 2502–2508, doi:10.3762/bjoc.13.247

• reported a novel multicomponent reaction for the synthesis of S-trifluoromethyl dithiocarbamates from secondary amines, CS2 and Togni's reagent in moderate to good yields. Under similar conditions, a primary amine afforded the corresponding isothiocyanate in excellent yield. The presence of dithiocarbamate

Mechanochemical synthesis of small organic molecules

• Tapas Kumar Achar,
• Anima Bose and
• Prasenjit Mal

Beilstein J. Org. Chem. 2017, 13, 1907–1931, doi:10.3762/bjoc.13.186

• [120]. Mechanochemical Hantzsch pyrrole synthesis [121]. Mechanochemical Biginelli reaction by subcomponent synthesis approach [133]. Mechanochemical asymmetric multicomponent reaction[134]. Mechanochemical Paal–Knorr pyrrole synthesis [142]. Mechanochemical synthesis of benzothiazole using ZnO nano