Applications of Isocyanides in IMCRs for the Rapid Generation of Molecular Diversity

Ayaz, Muhammad; Moliner, Fabio De; Dietrich, Justin; Hulme, Christopher

doi:10.1002/9783527652532.ch10

Cited by 21 publications

(18 citation statements)

References 141 publications

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“…Furthermore, a nearly limitless variety of heterocycles can be accessed through post-condensation transformations [5–7], adding only one to two steps to the synthetic sequence. However, the main drawback of the Ugi reaction is the poor stereochemical control that is typically achieved [8–9], which hampers its utilization in the diversity-oriented or target-oriented synthesis of complex chiral peptidomimetics.…”

Section: Resultsmentioning

confidence: 99%

Diastereoselective Ugi reaction of chiral 1,3-aminoalcohols derived from an organocatalytic Mannich reaction

Caputo¹,

Basso²,

Moni³

et al. 2016

Beilstein J. Org. Chem.

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SummaryEnantiomerically pure β-aminoalcohols, produced through an organocatalytic Mannich reaction, were subjected to an Ugi multicomponent reaction under classical or Lewis acid-promoted conditions with diastereoselectivities ranging from moderate to good. This approach represents a step-economical path to enantiomerically pure, polyfunctionalized peptidomimetics endowed with three stereogenic centers, allowing the introduction of five diversity inputs.

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Section: Resultsmentioning

confidence: 99%

Diastereoselective Ugi reaction of chiral 1,3-aminoalcohols derived from an organocatalytic Mannich reaction

Caputo¹,

Basso²,

Moni³

et al. 2016

Beilstein J. Org. Chem.

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“…9 Akin to the the Groebke-Blackburn-Bienaymé (GBB) condensation 10 that render bicyclic systems 4 (Scheme 1), it was postulated that the replacement of the heterocyclic input 3 with an amidine 5 would be sufficient to afford the desired chemotype 6 . However, after preliminary investigation of acid catalyzed promotion of this MCR, production of 6 was observed in only nominal yields <5% (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

MCRs reshaped into a switchable microwave-assisted protocol toward 5-aminoimidazoles and dihydrotriazines

et al. 2014

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A tunable microwave-assisted protocol for the synthesis of two biologically relevant families of heterocycles has been designed. Via a simple switch of reaction conditions, the same starting materials can be engaged in either an improved synthesis of the dihydrotriazine scaffold or a novel, first-in-class MCR to render the challenging 5-aminoimidazole nucleus in a single step. An additional first in class MCR is also reported utilizing guanidines to afford 2,5-aminoimidazoles.

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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).…”

Section: Multicomponent Reactions (Mcrs)mentioning

confidence: 99%

“…With respect to 1: New and in particular novel MCRs [ 38 , 45 , 61 , 81 , 82 , 112 , 113 , 154 , 157 , 174 , 175 , 176 , 177 , 178 ] are the basis and guarantee for high diversity and therewith the capacity to produce many structurally-different compounds. A method has been found to design MCRs going from libraries of compounds to libraries of reactions [ 176 ].…”

Section: Multicomponent Chemistry—the Futurementioning

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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Applications of Isocyanides in IMCRs for the Rapid Generation of Molecular Diversity

Cited by 21 publications

References 141 publications

Diastereoselective Ugi reaction of chiral 1,3-aminoalcohols derived from an organocatalytic Mannich reaction

Diastereoselective Ugi reaction of chiral 1,3-aminoalcohols derived from an organocatalytic Mannich reaction

MCRs reshaped into a switchable microwave-assisted protocol toward 5-aminoimidazoles and dihydrotriazines

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

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