Organic synthesis multicomponent reactions

Jacobi von Wangelin A, Neumann H, Gordes D et al (2003) Multicomponent coupling reactions for organic synthesis chemoselective reactions with amide-aldehyde mixtures. Chem Eur J 9 4286 294... 

Keywords Heterocycles Multicomponent reactions Microwave Organic synthesis... 

Mitchell, M. C., Spikmans, V., Bessoth, F., Manz, a., de Mello, A., Towards organic synthesis in microfluidic devices multicomponent reactions for the construction of compound libraries, in van den Berg, A., Olthuis, W., Bergveld,... 

Lombardo, M. Trombini, C. (1998) One-Pot Multicomponent Reactions. In Seminars in Organic Synthesis XXIII Summer School A. Corbella , pp. 7-32. Societa Chimica Italiana, MUan. 

Jean Rodriguez was born in Gieza, Spain, on 25 June 1958, and in 1959 his family emigrated to France. After studying chemistry at the University Paul Cezanne in Marseille, France, he completed his PhD as a CNRS student with Prof. B. Waegell and Prof. P. Brun in 1987. He completed his Habilitation in 1992, also at Marseille, where he is currently Professor and Director of the UMR-CNRS-6178-SYMBIO. His research interests include the development of domino and multicomponent reactions, and their applications in stereoselective synthesis. In 1998, he was awarded the Acros prize in Organic Chemistry from the French Chemical Society. 

To fully use the advantages afforded by multicomponent reaction systems in solid-phase organic synthesis, strategies in which each component is immobilized on the resin must be devised. In this way, individual components can be explored in terms of diversity without the restrictions imposed by immobilization. We have described solid-phase Mannich reactions1 of a resin-bound alkyne (see chapter 5), and we show here that the diversity of products using this chemistry can be enhanced when a different component of the reaction system is immobilized. Specifically, a secondary amine, piperazine, is bound to a resin and then treated with... 

Multicomponent reaction systems are highly valued in solid-phase organic synthesis because several elements of diversity can be introduced in a single transformation.1 The Mannich reaction is a classic example of a three-component system in which an active hydrogen component, such as a terminal alkyne, undergoes condensation with the putative imine species formed from the condensation of an amine with an aldehyde.2 The resultant Mannich adducts contain at least three potential sites for diversification specifically, each individual component—the amine, aldehyde, and alkyne—can be varied in structure and thus provide an element of diversity. 

Bremner WS, Organ MG (2007) Multicomponent reactions to form heterocycles by microwave-assisted continuous flow organic synthesis. J Comb Chem 9(1) 14—16... 

Microwave-assisted organic synthesis may also be used for carrying out the multicomponent reactions of ketones and 1,2-diamines [20, 21, 92, 100]. For example, the three-component reaction of o-PDA 1 with acetoacetic acid ethyl ester 83 and a series of aromatic and heteroaromatic aldehydes 84 proceeds under microwave irradiation with very high yields of diazepines 85 (up to 95%) [100]. Reaction of 2 equiv of cyclohexanone 86 with o-PDA 1 was also realized in a microwave field on a basic alumina surface in 4 min [92] (Scheme 4.27). 

This chapter contains a survey of free-radical-mediated multicomponent reactions (MCRs), which permit the coupling of three or more components. Even though they are not technically classified as MCRs, remarkable intramolecular radical cascade processes have been developed. Some examples, such as those shown in Scheme 6.3, use an isonitrile or acrylonitrile as the intermolecular component for each reaction [6]. These examples demonstrate the tremendous power of the combination of inter- and intramolecular radical cascade processes in organic synthesis. Readers are advised to be aware of remarkable intramolecular aspects of modem radical chemistry through excellent review articles published elsewhere [1, 7]. It should also be noted that there has also been remarkable progress in the area of living radical polymerizations, but this will not be covered here. 

Westman J (2004) Speed and Efficiency in the Production of Diverse Structures Microwave-Assisted Multicomponent Reactions. In LidstrOm P, Tierney JP (eds) Microwave-Assisted Organic Synthesis. Blackwell, Oxford, p 102... 

Abstract Increasing reaction speed and simplifying product purification are two major ways to improve the efficiency of organic synthesis. A new technology for high-speed solution-phase synthesis has been developed by combination of microwave heating and fluorous purification. This review describes different techniques for microwave-enhanced fluorous synthesis and their applications in Pd-catalyzed cross-coupling reactions, free-radical reactions, multicomponent reactions, and compound library synthesis. 

Dyker, G. Amino acid derivatives by multicomponent reactions. Organic Synthesis Highlights IV2000, 53-57. 

The use of ionic liquids in numerous organic transformations ranging from one-step to one-pot multicomponent reactions had been documented in the literature. In this account, we will provide a brief overview of some of the recent advancements in this area and depict that ionic liquids are indeed versatUe green solvents in organic synthesis. 

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