Synthesis of indole–cycloalkyl[b]pyridine hybrids via a four-component six-step tandem process

• Muthumani Muthu,
• Rakkappan Vishnu Priya,
• Abdulrahman I. Almansour,
• Raju Suresh Kumar and
• Raju Ranjith Kumar

Beilstein J. Org. Chem. 2018, 14, 2907–2915, doi:10.3762/bjoc.14.269

• –C bond forming reaction [57] and three-component reactions of aromatic aldehydes, 3-(1H-indol-3-yl)-3-oxopropanenitrile and malononitrile [58][59], 2-acetylpyridine [60] or 3-amino-2-enones [61]. Incidentally, the indole scaffold is found in several natural products and bioactive synthetic compounds

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

• investigation on the catalytic cyclization during Kabachnik–Fields reactions of acetylenic aldehydes with aromatic amines and dialkyl phosphonates has been reported by Čikotienė et al. [50]. They found that the cyclization type during these three-component reactions strongly depends on the nature of the

• stereoselective synthesis of 1,2-dihydroquinolin-2-ylphosphonates 271 and 1,2-dihydroisoquinolin-1-ylphosphonates 272 via the three-component reactions of quinoline or isoquinoline, dialkyl acetylenedicarboxylates 269, and dialkyl phosphonates 270 has been described by Shaabani et al. (Scheme 56) [94]. The

• -phosphonates and 2-acyl-1,2-dihydroisoquinoline-1-phosphonates. Three-component reaction of pyridine derivatives with ethyl propiolate and dialkyl phosphonates. Three-component reactions for the phosphorylation of benzothiazole and isoquinoline. Three-component synthesis of diphenyl [2-(aminocarbonyl)- or [2

Recent advances in N-heterocyclic carbene (NHC)-catalysed benzoin reactions

• Rajeev S. Menon,
• Akkattu T. Biju and
• Vijay Nair

Beilstein J. Org. Chem. 2016, 12, 444–461, doi:10.3762/bjoc.12.47

• of formahydroxamic esters constitutes a valuable addition to a thin list of NHC-mediated three-component reactions. Intramolecular benzoin reactions One of the earliest reports of an intramolecular benzoin condensation appeared in 1976. Cookson and Lane found that the treatment of anhydrous

The unexpected influence of aryl substituents in N-aryl-3-oxobutanamides on the behavior of their multicomponent reactions with 5-amino-3-methylisoxazole and salicylaldehyde

• Volodymyr V. Tkachenko,
• Elena A. Muravyova,
• Sergey M. Desenko,
• Oleg V. Shishkin,
• Svetlana V. Shishkina,
• Dmytro O. Sysoiev,
• Thomas J. J. Müller and
• Valentin A. Chebanov

Beilstein J. Org. Chem. 2014, 10, 3019–3030, doi:10.3762/bjoc.10.320

• , Universitätsstraße 1, D-40225 Düsseldorf, Germany 10.3762/bjoc.10.320 Abstract The switchable three-component reactions of 5-amino-3-methylisoxazole, salicylaldehyde and N-aryl-3-oxobutanamides under different conditions were studied and discussed. The unexpected influence of the aryl substituent in N-aryl-3

• rise either to pyrazolopyridine or pyrazolopyrimidine heterocycles. In the authors' opinion, the different outcomes in three-component reactions involving 3-methyl- or 3-aryl-substituted 5-aminopyrazoles can mainly be put down to the steric substituent effect [11]. It is noteworthy to mention that

• . In all cases of three-component reactions involving aminoazoles and carbonyl compounds, which were previously studied in our group [13][18][21][22][23][24], the substitution of mechanical stirring by ultrasonication did not change the structure of the final products but only affected the purity and

New highlights of the syntheses of pyrrolo[1,2-a]quinoxalin-4-ones

• Emilian Georgescu,
• Alina Nicolescu,
• Florentina Georgescu,
• Florina Teodorescu,
• Daniela Marinescu,
• Ana-Maria Macsim and
• Calin Deleanu

Beilstein J. Org. Chem. 2014, 10, 2377–2387, doi:10.3762/bjoc.10.248

• Bucharest, Romania Petru Poni Institute of Macromolecular Chemistry, Romanian Academy, Aleea Grigore Ghica Voda 41-A, RO-700487 Iasi, Romania Research Dept., Teso Spec SRL, Str. Muncii 53, RO-915200 Fundulea, Calarasi, Romania 10.3762/bjoc.10.248 Abstract The one-pot three-component reactions of 1

• . Keywords: 1,3-dipolar cycloadditions; multicomponent; one-pot three-component reactions; pyrrolo[1,2-a]benzimidazole; pyrrolo[1,2-a]quinoxalin-4-one; Introduction The pyrrolo[1,2-a]quinoxaline system has significant biological activities and is a subject fo constant interest. This skeleton is a

• towards N-bridged heterocyclic compounds [17][18][19][20] prompted us to investigate the one-pot three-component reactions of various substituted benzimidazoles with alkyl bromoacetates and electron-deficient alkynes in presence of an epoxide. Herein, we report a simple one-pot three-component synthetic

Multicomponent reactions in nucleoside chemistry

• Mariola Koszytkowska-Stawińska and
• Włodzimierz Buchowicz

Beilstein J. Org. Chem. 2014, 10, 1706–1732, doi:10.3762/bjoc.10.179

• the addition of the nucleoside moiety to the C-1 or C-2 carbon atom of the C=C double bond. The three-component reactions of nucleoside-derived (uridine or thymidine) allenes 97, a range of aryl iodides, and 1-adamantylamine was accomplished smoothly under the palladium-catalyzed conditions (Scheme 40

Use of activated enol ethers in the synthesis of pyrazoles: reactions with hydrazine and a study of pyrazole tautomerism

• Denisa Tarabová,
• Stanislava Šoralová,
• Martin Breza,
• Marek Fronc,
• Wolfgang Holzer and
• Viktor Milata

Beilstein J. Org. Chem. 2014, 10, 752–760, doi:10.3762/bjoc.10.70

• ethoxymethylidenemalonate (EMME, 3c), and 3-(ethoxymethylidene)pentane-2,4-dione (EMAA, 3d) were employed. Three-component reactions (hydrazine + trialkylorthoformate + active methylidene component) were not studied. The products resulting from the reaction of a hydrazine hydrate with activated symmetrical enol ethers 3

A novel family of (1-aminoalkyl)(trifluoromethyl)- and -(difluoromethyl)phosphinic acids – analogues of α-amino acids

• Natalia V. Pavlenko,
• Tatiana I. Oos,
• Yurii L. Yagupolskii,
• Igor I. Gerus,
• Uwe Doeller and
• Lothar Willms

Beilstein J. Org. Chem. 2014, 10, 722–731, doi:10.3762/bjoc.10.66

• NaHCO3, as a viscous undistillable liquid, which was stable for weeks on storage. Three-component reactions At the outset of our work three-component reactions of formaldehyde, dibenzylamine and the esters 2 or 5 were explored as model transformations to evaluate the feasibility of the Kabachnik–Fields

• azomethines The addition of the P–H functionality to C=N double bonds is a very general procedure for the formation of P–C–N systems. Based on our experience of these three-component reactions (Scheme 2 and Scheme 3) we investigated the scope and limitations of the addition of (trifluoromethyl)phosphinic acid

• ), 6.9 (dm, 1JHP = 566.5 Hz, 1H, PH), 12.7 (s, 1H, OH); 31P NMR (121 MHz) δP 12.1 (dtd, 1JPH = 566 Hz, 2JPF = 86 Hz, 2JPH = 25 Hz); 19F NMR (188 MHz) δF 9.6 (dd, 2JFP = 86 Hz, 2JFH = 49 Hz ). Three-component reactions The general procedure for the condensation of the acid 1 with dibenzylamine and

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

• as a powerful tool for the synthesis of medium-sized libraries of bioactive compounds. Thus, straightforward syntheses of 1,3-disubstituted-1,2-dihydroisoquinolines have been achieved by three-component reactions between alkynylbenzaldehydes 25 (γ-carbonylalkyne), primary amines 26 (mainly anilines

• been reported [59]. Preformed 2-(1-alkynyl)arylaldimines 27 have been used in a MCR involving tandem cyclization/three-component reactions with diazo compounds 37 and water or alcohols 38 in the presence of dirhodium acetate and silver triflate cooperative catalysis resulting in excellent yields of

A catalyst-free multicomponent domino sequence for the diastereoselective synthesis of (E)-3-[2-arylcarbonyl-3-(arylamino)allyl]chromen-4-ones

• Pitchaimani Prasanna,
• Pethaiah Gunasekaran,
• Subbu Perumal and
• J. Carlos Menéndez

Beilstein J. Org. Chem. 2014, 10, 459–465, doi:10.3762/bjoc.10.43

• transformations [43][44][45][46][47][48][49][50][51][52][53][54]. In order to achieve our goal, we embarked on the study of the three-component reactions between 3-formylchromone (1), (E)-3-(dimethylamino)-1-arylprop-2-en-1-ones 2 and anilines 3, which we expected to furnish novel (E)-3-[2-arylcarbonyl-3

The Flögel-three-component reaction with dicarboxylic acids – an approach to bis(β-alkoxy-β-ketoenamides) for the synthesis of complex pyridine and pyrimidine derivatives

• Mrinal K. Bera,
• Moisés Domínguez,
• Paul Hommes and
• Hans-Ulrich Reissig

Beilstein J. Org. Chem. 2014, 10, 394–404, doi:10.3762/bjoc.10.37

• aromatic rings. Flögel-three-component reaction of lithiated alkoxyallenes, nitriles and carboxylic acids providing β-alkoxy-β-ketoenamides 1 – versatile precursors for the synthesis of functionalized N-heteroaromatics 2–6. Synthesis of bis(β-ketoenamides) 13–15 by three-component reactions of lithiated

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

• Jie-Ping Wan Yunfang Lin Kaikai Hu Yunyun Liu Key Laboratory of Functional Small Organic Molecules, Ministry of Education and College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330022, P. R. China 10.3762/bjoc.10.25 Abstract The three-component reactions of

Organobase-catalyzed three-component reactions for the synthesis of 4H-2-aminopyrans, condensed pyrans and polysubstituted benzenes

• Moustafa Sherief Moustafa,
• Saleh Mohammed Al-Mousawi,
• Maghraby Ali Selim,
• Ahmed Mohamed Mosallam and
• Mohamed Hilmy Elnagdi

Beilstein J. Org. Chem. 2014, 10, 141–149, doi:10.3762/bjoc.10.11

The regioselective synthesis of spirooxindolo pyrrolidines and pyrrolizidines via three-component reactions of acrylamides and aroylacrylic acids with isatins and α-amino acids

• Tatyana L. Pavlovskaya,
• Fedor G. Yaremenko,
• Victoria V. Lipson,
• Svetlana V. Shishkina,
• Oleg V. Shishkin,
• Vladimir I. Musatov and
• Alexander S. Karpenko

Beilstein J. Org. Chem. 2014, 10, 117–126, doi:10.3762/bjoc.10.8

Synthesis of spiro[dihydropyridine-oxindoles] via three-component reaction of arylamine, isatin and cyclopentane-1,3-dione

• Yan Sun,
• Jing Sun and
• Chao-Guo Yan

Beilstein J. Org. Chem. 2013, 9, 8–14, doi:10.3762/bjoc.9.2

• cyclopentane-1,3-dione (b). Condensation reactions of isatins with cyclopentane-1,3-dione. Proposed reaction mechanism for the three-component reaction. Synthesis of spiro[dihydropyridine-oxindole] from three-component reactions. Synthesis of spiro[dihydropyridine-oxindole] from three-component reactions

• -component reactions of arylamine, isatin and cyclopentane-1,3-dione in acetic acid at room temperature. On the other hand the condensation of isatin with two equivalents of cyclopentane-1,3-dione gave 3,3-bis(2-hydroxy-5-oxo-cyclopent-1-enyl)oxindole in high yields. The reaction mechanism and substrate

• Yan Sun Jing Sun Chao-Guo Yan College of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou 225002, China 10.3762/bjoc.9.2 Abstract A fast and convenient protocol for the synthesis of novel spiro[dihydropyridine-oxindole] derivatives in satisfactory yields was developed by the three

Solvent-free and time-efficient Suzuki–Miyaura reaction in a ball mill: the solid reagent system KF–Al₂O₃ under inspection

• Franziska Bernhardt,
• Ronald Trotzki,
• Tony Szuppa,
• Achim Stolle and
• Bernd Ondruschka

Beilstein J. Org. Chem. 2010, 6, No. 7, doi:10.3762/bjoc.6.7

• neutral to basic aluminas has been recently shown in three-component reactions affording thiochromeno[2,3-b]pyridine derivatives [24]. The results were in clear contrast to that of the microwave-assisted Pd(PPh3)4-catalyzed solid-state Suzuki–Miyaura reaction protocol presented by Saha et al., revealing