Multicomponent Reactions Based on Nucleophilic Carbenes and Their Applications in Organic Synthesis

Nair, Vijay; Menon, Rajeev S.; Vellalath, Sreekumar

doi:10.1002/chin.200551247

Cited by 2 publications

(2 citation statements)

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“…IMCRs [ 38 , 42 , 43 , 44 , 45 , 46 , 47 , 48 , 49 , 50 ], alkyne-based [ 38 , 51 , 52 , 53 , 54 ] and C-H-acidic compound [ 55 , 56 , 57 , 58 , 59 , 60 ]-based MCRs in particular have a high potential to be very diverse. Many novel MCRs [ 57 , 58 , 59 , 60 , 61 , 62 , 63 , 64 , 65 , 66 , 67 , 68 , 69 , 70 , 71 , 72 , 73 ] have meanwhile become part of the range of syntheses, e.g., boron-mediated [ 62 , 66 ], photo-induced [ 67 ] and carbene-based MCRs [ 72 ] such as N-heterocyclic carbenes (NHCs). They all increase the application options for MCRs, such as MCR nanosystems and mechanochemical reactions [ 65 ].…”

Section: Multicomponent Reactions (Mcrs)mentioning

confidence: 99%

Synergy Effects in the Chemical Synthesis and Extensions of Multicomponent Reactions (MCRs)—The Low Energy Way to Ultra-Short Syntheses of Tailor-Made Molecules

Eckert

2017

Molecules

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Several novel methods, catalysts and reagents have been developed to improve organic synthesis. Synergistic effects between reactions, reagents and catalysts can lead to minor heats of reaction and occur as an inherent result of multicomponent reactions (MCRs) and their extensions. They enable syntheses to be performed at a low energy level and the number of synthesis steps to be drastically reduced in comparison with ‘classical’ two-component reactions, fulfilling the rules of Green Chemistry. The very high potential for variability, diversity and complexity of MCRs additionally generates an extremely diverse range of products, thus bringing us closer to the aim of being able to produce tailor-made and extremely low-cost materials, drugs and compound libraries.

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Section: Multicomponent Reactions (Mcrs)mentioning

confidence: 99%

Synergy Effects in the Chemical Synthesis and Extensions of Multicomponent Reactions (MCRs)—The Low Energy Way to Ultra-Short Syntheses of Tailor-Made Molecules

Eckert

2017

Molecules

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“…They are therefore attractive to synthetic and process chemists because they fulfill many of the optimization requirements that concatenation of steps in a telescoped sequence achieve such as reduced solvent demand as a direct result of reduced isolations of intermediates. Because the discovery of new MCRs is now a vigorous area of research particularly in the context of green chemistry, several reviews − and a book have been written on these kinds of reactions. Ugi has noted, however, that the invention of multicomponent reactions goes back to the 19th century.…”

Section: Introductionmentioning

confidence: 99%

On the Probability That Ring-Forming Multicomponent Reactions Are Intrinsically Green: Setting Thresholds for Intrinsic Greenness Based on Design Strategy and Experimental Reaction Performance

Andraos¹

2013

ACS Sustainable Chem. Eng.

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This paper describes in detail the determination of the likelihood that a given generalized chemical reaction may be considered intrinsically “green” based on design strategy. Justification is given for setting threshold constraints on reaction yield and kernel reaction mass efficiency (RME) performances at greater than 80% and greater than 61.8%, respectively, for intrinsically green reactions. These criteria are applied to a survey of 60 named ring-forming multicomponent reactions (MCRs) and 2000+ such reactions reported in the literature from 2003 to 2011. Patterns among various ring construction motifs are discussed. Results show that 5- and 6-membered monocyclic rings are most commonly made by [2+2+1] and [3+2+1] cycloadditions where 57% and 76% of them, respectively, have a 100% chance of being intrinsically green from a design perspective. Similarly, the [4.3.0] and [4.4.0] skeletons are the most common fused bicyclic structures made by MCR strategies where 38% and 59% of them, respectively, have a 100% chance of being intrinsically green. The syntheses of various heterocyclic ring structures made by MCRs have also been surveyed using this new criterion. The application of this probability analysis is also demonstrated for the total synthesis of ring containing scaffold structures of praziquantel and frondosin B, two compounds of pharmaceutical interest made using MCRs. The direction of future research in MCR development is also briefly discussed.

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Multicomponent Reactions Based on Nucleophilic Carbenes and Their Applications in Organic Synthesis

Abstract: For Abstract see ChemInform Abstract in Full Text.

Cited by 2 publications

References 1 publication

Synergy Effects in the Chemical Synthesis and Extensions of Multicomponent Reactions (MCRs)—The Low Energy Way to Ultra-Short Syntheses of Tailor-Made Molecules

Synergy Effects in the Chemical Synthesis and Extensions of Multicomponent Reactions (MCRs)—The Low Energy Way to Ultra-Short Syntheses of Tailor-Made Molecules

On the Probability That Ring-Forming Multicomponent Reactions Are Intrinsically Green: Setting Thresholds for Intrinsic Greenness Based on Design Strategy and Experimental Reaction Performance

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