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

Features of the behavior of 4-amino-5-carboxamido-1,2,3-triazole in multicomponent heterocyclizations with carbonyl compounds

• Eugene S. Gladkov,
• Katerina A. Gura,
• Svetlana M. Sirko,
• Sergey M. Desenko,
• Ulrich Groth and
• Valentin A. Chebanov

Beilstein J. Org. Chem. 2012, 8, 2100–2105, doi:10.3762/bjoc.8.236

• . Multicomponent synthesis of 4,5,6,7,8,9-hexahydro[1,2,3]triazolo[5,1-b]quinazoline-3-carboxamides 4a–c, 7 and 9a–j. Supporting Information Supporting Information File 322: Experimental details and characterization data for all new compounds. Acknowledgments ESG is grateful for financial support to DAAD

Enaminones in a multicomponent synthesis of 4-aryldihydropyridines for potential applications in photoinduced intramolecular electron-transfer systems

• Nouria A. Al-Awadi,
• Maher R. Ibrahim,
• Mohamed H. Elnagdi,
• Elizabeth John and
• Yehia A. Ibrahim

Beilstein J. Org. Chem. 2012, 8, 441–447, doi:10.3762/bjoc.8.50

Amines as key building blocks in Pd-assisted multicomponent processes

• Didier Bouyssi,
• Nuno Monteiro and
• Geneviève Balme

Beilstein J. Org. Chem. 2011, 7, 1387–1406, doi:10.3762/bjoc.7.163

• sulfur dioxide. However, this Pd-catalyzed aminosulfonylation process proved inefficient with primary amines (Scheme 20) [20]. Multicomponent synthesis of nitrogen-containing heterocycles may also be initiated by an aza-Michael addition and terminated by a palladium-catalyzed ring-closure process [21

Multicomponent synthesis of artificial nucleases and their RNase and DNase activity

• Anton V. Gulevich,
• Lyudmila S. Koroleva,
• Olga V. Morozova,
• Valentina N. Bakhvalova,
• Vladimir N. Silnikov and
• Valentine G. Nenajdenko

Beilstein J. Org. Chem. 2011, 7, 1135–1140, doi:10.3762/bjoc.7.131

• task in organic and biomolecular chemistry. In this paper we present the rational design, multicomponent synthesis, and RT-qPCR quantitation of nuclease activity of novel amino acids derivatives. Results and Discussion Recently, a number of artificial peptide ribonucleases modeling known catalytic