Unravelling a trichloroacetic acid-catalyzed cascade access to benzo[f]chromeno[2,3-h]quinoxalinoporphyrins

• Chandra Sekhar Tekuri,
• Pargat Singh and
• Mahendra Nath

Beilstein J. Org. Chem. 2023, 19, 1216–1224, doi:10.3762/bjoc.19.89

• ; multicomponent synthesis; one-pot reaction; trichloroacetic acid; Introduction π-Conjugated porphyrin macrocycles are known for their applications in numerous areas ranging from oxygen transport, photosynthesis, catalysis and medicine [1][2][3]. In the past several years, diverse organic scaffolds have been

DDQ in mechanochemical C–N coupling reactions

• Shyamal Kanti Bera,
• Rosalin Bhanja and
• Prasenjit Mal

Beilstein J. Org. Chem. 2022, 18, 639–646, doi:10.3762/bjoc.18.64

• ten innovative technologies that IUPAC recognized [7]. To perform organic transformations in a greener way, the mechanochemical methods can also be considered as one of the alternative approaches [8][9][10]. The one-pot multicomponent synthesis of important heterocycles can be the state of art

Asymmetric organocatalyzed synthesis of coumarin derivatives

• Natália M. Moreira,
• Lorena S. R. Martelli and
• Arlene G. Corrêa

Beilstein J. Org. Chem. 2021, 17, 1952–1980, doi:10.3762/bjoc.17.128

• as harsh reaction conditions, has become paramount in the field of organic synthesis in recent years [19]. In this sense, Molnar et al. published a review on green chemistry approaches to the synthesis of coumarin derivatives [20] and Chandrakar et al. reviewed the developments of multicomponent

• synthesis of biologically relevant coumarins in aqueous medium [21]. Catalysis is one of the fundamental pillars of green chemistry [22], and the transition-metal-catalyzed synthesis of coumarins has been reviewed by Sharma et al. [23]. More recently, Kanchana et al. published an account on the palladium

Microwave-assisted multicomponent reactions in heterocyclic chemistry and mechanistic aspects

• Shivani Gulati,
• Stephy Elza John and
• Nagula Shankaraiah

Beilstein J. Org. Chem. 2021, 17, 819–865, doi:10.3762/bjoc.17.71

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

• heterogeneous nanocatalyst in “click” reactions for the multicomponent synthesis of triazole products in water with ultrasound irradiation and 0.017 mol % catalyst loading. As such, a series of aryl/alkyl-substituted oxiranes was treated with sodium azide and nonactivated terminal alkynes, giving 1,2,3-triazole

Emission solvatochromic, solid-state and aggregation-induced emissive α-pyrones and emission-tuneable 1H-pyridines by Michael addition–cyclocondensation sequences

• Natascha Breuer,
• Irina Gruber,
• Christoph Janiak and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2019, 15, 2684–2703, doi:10.3762/bjoc.15.262

• to α-pyrones through a consecutive alkynylation–Michael addition–cyclocondensation (AMAC) multicomponent synthesis [23]. The reaction can be rationalized by a Sonogashira coupling between an acid chloride and a terminal alkyne furnishing an alkynone, which is transformed without isolation by addition

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

• comprises an initial Ugi-azide-4CR followed by a cyclization step, involving some of the reactive functionalities previously installed in the multicomponent process [20][21][22][23][24][25][26]. However, the interplay between the multicomponent synthesis of tetrazoles and metal-catalyzed cyclization

In water multicomponent synthesis of low-molecular-mass 4,7-dihydrotetrazolo[1,5-a]pyrimidines

• Irina G. Tkachenko,
• Sergey A. Komykhov,
• Vladimir I. Musatov,
• Svitlana V. Shishkina,
• Viktoriya V. Dyakonenko,
• Vladimir N. Shvets,
• Mikhail V. Diachkov,
• Valentyn A. Chebanov and
• Sergey M. Desenko

Beilstein J. Org. Chem. 2019, 15, 2390–2397, doi:10.3762/bjoc.15.231

• was assayed with 1,1-diphenyl-2-picrylhydrazyl. Keywords: 5-aminotetrazole; antioxidant activity; 1,3-dicarbonyl compounds; multicomponent synthesis; tetrazolo[1,5-a]pyrimidines; Introduction Tetrazolo[1,5-a]pyrimidines and their partially hydrogenated derivatives are known for their interesting

• multicomponent approach to minimize the number of reaction steps according to green chemistry principles as well. Based on our recent research [26][27][28], where water proved to be an effective solvent for the multicomponent synthesis of low-molecular-mass dihydroazolopyrimidines, we decided to use water also

Steroid diversification by multicomponent reactions

• Leslie Reguera,
• Cecilia I. Attorresi,
• Javier A. Ramírez and
• Daniel G. Rivera

Beilstein J. Org. Chem. 2019, 15, 1236–1256, doi:10.3762/bjoc.15.121

• promise for the future development of peptide pharmaceuticals. 5 Multicomponent synthesis of steroidal macrocycles and cages Since the beginning of this century, the field of macrocycle synthesis has witnessed the emergence of MCRs as effective ring closing procedures, including the cyclization of large

• -diketopiperazines based on a diastereoselective Ugi-4CR with an androstanic aldehyde derived from dehydroepiandrosterone (DHEA) [16]. Multicomponent synthesis of a heterocycle–steroid hybrid using a ketosteroid as carbonyl component [18]. Synthesis of peptidomimetic–steroid hybrids using the Ugi-4CR with

• ]. Synthesis of ecdysteroid derivatives by Ugi-4CR using a steroidal isocyanide [30]. Stereoselective multicomponent synthesis of a steroid–tetrahydropyridine hybrid using a chiral bifunctional substrate and a cholestanic isocyanide. DBA: 3,5-dinitrobenzoic acid [31]. Pd(II)-catalyzed three-component reaction

Ugi reaction-derived prolyl peptide catalysts grafted on the renewable polymer polyfurfuryl alcohol for applications in heterogeneous enamine catalysis

• Alexander F. de la Torre,
• Gabriel S. Scatena,
• Oscar Valdés,
• Daniel G. Rivera and
• Márcio W. Paixão

Beilstein J. Org. Chem. 2019, 15, 1210–1216, doi:10.3762/bjoc.15.118

• Abstract The multicomponent synthesis of prolyl pseudo-peptide catalysts using the Ugi reaction with furfurylamines or isocyanides is described. The incorporation of such a polymerizable furan handle enabled the subsequent polymerization of the peptide catalyst with furfuryl alcohol, thus rendering

• catalysts for applications in continuous-flow catalysis [8]. In an endeavor to develop a cheaper and renewable polymer-supported organocatalyst, herein we describe the multicomponent synthesis of furfuryl-containing prolyl pseudo-peptide catalysts and their subsequent utilization in the preparation of PFA

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

• multicomponent synthesis of isoindolinones II and 2-oxindoles III (Figure 1), where the setup of the γ-lactam core takes place during the key process. MCRs involve the simultaneous reaction between three or more reactants to deliver products that include significant fragments of all the substrates in their

• , leading to final lactams 20. This mechanism is partially corroborated by the following multicomponent synthesis where benzamide 21, ortho-functionalized with a terminal alkyne group (Scheme 5), a secondary amine 22 and carbon monoxide (23) react to produce 3-methyleneisoindolinones 24 [80]. A palladium

• yields (22 examples, 82–97% yields) [94]. On the contrary, another Strecker multicomponent synthesis, between 2-formylbenzoate 29, benzylamine and potassium cyanide, carried out under mechanochemical conditions and zinc catalysis, only produced a 31% yield of the corresponding cyanoisoindolinone 53a (R1

Ruthenium-based olefin metathesis catalysts with monodentate unsymmetrical NHC ligands

• Veronica Paradiso,
• Chiara Costabile and
• Fabia Grisi

Beilstein J. Org. Chem. 2018, 14, 3122–3149, doi:10.3762/bjoc.14.292

• metathesis of 96 (Table 4, entries 8 and 9, respectively). Indeed, the one-step multicomponent synthesis of unsaturated unsymmetrical NHCs could provide a cost-effective alternative to the multistep synthesis of their saturated counterparts [36]. The catalyst 85 was identified as the catalyst of choice for

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

• the 3-methyl-5-methylsulfanyl-4-phenylselanyl-1H-pyrazole [10]. Our research group described the multicomponent synthesis of 3,5-dimethyl-4-arylselanyl-1H-pyrazoles catalyzed by copper iodide using DMSO as solvent [4]. More recently, Zora and co-workers reported the one-pot preparation of 4

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

• . [Dsim]HSO4 (26) has been also employed as a reusable and efficient catalyst for the one-pot multicomponent synthesis of various xanthene derivatives 24, 27, and 28 and pyrimido[4,5-b]quinoline derivatives 30 under mild and green conditions (Scheme 4) [42][43][44]. Easy preparation of the catalyst, easy

• copolymer synthesized by Friedel–Crafts alkylation of triphenylamine (115) with dibromo-p-xylene 112 was prepared (Scheme 21). After the sulfonation process, the resulted material has been employed as a heterogeneous, reusable, and environmentally benign catalyst in the multicomponent synthesis 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

• ). Bhaumik et al. [59] carried out a similar reaction of 5-aminopyrazole (R = H, R1 = Me, 16), isatin 54 and cyclic-1,3-diones 58 in aqueous ethanol using aluminosilicate nanoparticles catalyst to yield pyrazolo[3,4-b]pyridines 61 (Scheme 13). Dandia et al. [60] carried out the multicomponent synthesis of

CF₃SO₂X (X = Na, Cl) as reagents for trifluoromethylation, trifluoromethylsulfenyl-, -sulfinyl- and -sulfonylation. Part 1: Use of CF₃SO₂Na

• Hélène Guyon,
• Hélène Chachignon and
• Dominique Cahard

Beilstein J. Org. Chem. 2017, 13, 2764–2799, doi:10.3762/bjoc.13.272

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

• ]. b) Multistep and multicomponent synthesis of Re-complexes [176]. c) Mechano-synthesis of NHC-Au complex [177]. Mechanochemical activation of C–H bond of unsymmetrical azobenzene [178]. Mechanochemical synthesis of organometallic pincer complex [179]. Mechanochemical synthesis of tris(allyl)aluminum

Multicomponent synthesis of spiropyrrolidine analogues derived from vinylindole/indazole by a 1,3-dipolar cycloaddition reaction

• Manjunatha Narayanarao,
• Lokesh Koodlur,
• Vijayakumar G. Revanasiddappa,
• Subramanya Gopal and
• Susmita Kamila

Beilstein J. Org. Chem. 2016, 12, 2893–2897, doi:10.3762/bjoc.12.288

• -pot multicomponent synthesis. The method uses the 1,3-dipolar cycloaddition reaction between N-alkylvinylindole/indazole and azomethine ylides, prepared in situ from cyclic/acyclic amino acids. The 1,3-dipolar cycloaddition proceeds efficiently under thermal conditions to afford the regio- and

Multicomponent reactions: A simple and efficient route to heterocyclic phosphonates

• Mohammad Haji

Beilstein J. Org. Chem. 2016, 12, 1269–1301, doi:10.3762/bjoc.12.121

• about the multicomponent synthesis of phosphono-substituted heterocycles has been reported so far. This review focuses on general multicomponent reactions as well as on modified MCR towards heterocyclic phosphonates. It is organized by the reaction types and covers literature published up to September

• multicomponent synthesis of benzodiazepinylphosphonates in the literature. Both syntheses are based on o-diaminobenzene as the starting material. In the first method, an YbCl3-catalyzed three-component reaction between an o-diaminobenzene 124, 2,4-pentanedione (125) and diethyl phosphite under optimized solvent

• reaction can be considered the starting point of multicomponent synthesis of this class of compounds. However, the major advancements in this interesting field have been achieved in recent years. More than 75% of the cited literature in this review has been published within the last six years, of which

(Thio)urea-mediated synthesis of functionalized six-membered rings with multiple chiral centers

• Giorgos Koutoulogenis,
• Nikolaos Kaplaneris and
• Christoforos G. Kokotos

Beilstein J. Org. Chem. 2016, 12, 462–495, doi:10.3762/bjoc.12.48

• in the production of 93 and 94 in moderate to excellent enantioselectivities, considering the high molecular complexity achieved in only one step. Recently, Bugaut, Constantieux and co-workers described the enantioselective organocatalytic multicomponent synthesis of 2,6-diazabicyclo[2.2.2]octanones

Copper-catalyzed asymmetric conjugate addition of organometallic reagents to extended Michael acceptors

• Thibault E. Schmid,
• Sammy Drissi-Amraoui,
• Christophe Crévisy,
• Olivier Baslé and
• Marc Mauduit

Beilstein J. Org. Chem. 2015, 11, 2418–2434, doi:10.3762/bjoc.11.263

• catalytic applications [22][23]. Amongst the myriad of available NHC ligands, chiral unsymmetrical NHC ligands appeared as particularly potent in asymmetric catalysis, and were investigated in copper-catalyzed conjugate additions [24]. Recently, a multicomponent synthesis enabled the facile access to a wide

Rapid pseudo five-component synthesis of intensively blue luminescent 2,5-di(hetero)arylfurans via a Sonogashira–Glaser cyclization sequence

• Fabian Klukas,
• Alexander Grunwald,
• Franziska Menschel and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2014, 10, 672–679, doi:10.3762/bjoc.10.60

• Sonogashira–Glaser sequence we recently presented a straightforward one-pot sequence for the synthesis of 2,5-di(hetero)arylthiophenes [38]. Here, we report the methodological development of a novel multicomponent synthesis of symmetrical 2,5-(hetero)arylfurans in the sense of a consecutive one-pot sequence

Silver and gold-catalyzed multicomponent reactions

• Giorgio Abbiati and
• Elisabetta Rossi

Beilstein J. Org. Chem. 2014, 10, 481–513, doi:10.3762/bjoc.10.46

• expensive ligands and often harsh bases, whereas the silver-mediated process depends on a simple but efficient catalyst such as AgI and Cs2CO3 as base. This feature has been clearly highlighted by Anastas who realized the multicomponent synthesis of regioisomeric arylnaphthalene lactones 89 and 90 from

A new manganese-mediated, cobalt-catalyzed three-component synthesis of (diarylmethyl)sulfonamides

• Antoine Pignon,
• Erwan Le Gall and
• Thierry Martens

Beilstein J. Org. Chem. 2014, 10, 425–431, doi:10.3762/bjoc.10.39

• multicomponent procedure intended to the synthesis of N-protected (diarymethyl)amines and related compounds would be highly desirable. In preceding works, we described the Mannich-like multicomponent synthesis of α-branched amines from organic halides, aldehydes and amines, using a zinc-mediated process [35][36

• intermediate H [40] to form the imine III and as a nucleophile furnishing 4 by trapping III. Conclusion In conclusion, the results presented in this study indicate that the manganese(0)/cobalt(II) system is a suitable combination for the multicomponent synthesis of (diarylmethyl)sulfonamides and related

Secondary amine-initiated three-component synthesis of 3,4-dihydropyrimidinones and thiones involving alkynes, aldehydes and thiourea/urea

• Jie-Ping Wan,
• Yunfang Lin,
• Kaikai Hu and
• Yunyun Liu

Beilstein J. Org. Chem. 2014, 10, 287–292, doi:10.3762/bjoc.10.25

• DHPMs, the utilization of new C5–C6 fragment donors constituted the major strategy. Representative new C5–C6 building blocks used in the multicomponent synthesis of DHPMs are 2-oxosuccinic acid [27], acetylaldehydes [28], cyclic and acyclic ketones [29][30][31], β-oxo dithioesters [32], diketenes [33

• solid. Some DHPMs-based lead compounds. Regioselective 1,3-thiazines and DHPMs via aldehydes, ureas/thioureas and alkynes. Synthesis of enamino ester intermediate and its transformation to DHPM. Proposed reaction mechanism. Optimization of reaction conditionsa. Multicomponent synthesis of different