Trityl Isocyanide as a Mechanistic Probe in Multicomponent Chemistry: Walking the Line between Ugi- and Strecker-type Reactions.

doi:10.1002/chem.201600285

Paper

Trityl Isocyanide as a Mechanistic Probe in Multicomponent Chemistry: Walking the Line between Ugi- and Strecker-type Reactions.

Published Jun 1, 2016 · R. Cioc, H. D. Preschel, Gydo van der Heijden

Chemistry

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Abstract

Herein, we describe the versatile application of triphenylmethyl (trityl) isocyanide in multicomponent chemistry. This reagent can be employed as a cyanide source in the Strecker reaction and as convertible isocyanide in the preparation of N-acyl amino acids by Ugi 4CR/detritylation and free imidazo[1,2-a]pyridin-3-amines by a Groebke-Blackburn-Bienaymé 3CR condensation/deprotection protocol. The mechanisms of these three classical MCRs intersect at the common N-trityl nitrilium ion intermediate, whose predictable reactivity can be exploited towards chemoselective transformations.

Study Snapshot

Trityl isocyanide can be used as a versatile reagent in multicomponent chemistry, enabling chemoselective transformations by interacting with N-trityl nitrilium ion intermediates in Ugi and Strecker reactions.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Trityl Isocyanide as a Mechanistic Probe in Multicomponent Chemistry: Walking the Line between Ugi- and Strecker-type Reactions.

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References

Synthesis of tetrazoles via isocyanide-based reactions

Isocyanide-based reactions can be divided into four classes: two-component reactions (2CRs), Passerini-azide three-component reactions (PA-3CRs), Ugi-azide four-component reactions (UA-4CRs) and Ugi-azide three-

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Multicomponent reactions (MCRs) have advanced in synthesising structurally diverse sugar-based derivatives, benefiting society and drug discovery.

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This one-pot process efficiently synthesizes complex natural product hybrids by combining organocatalysis with multicomponent reactions, leading to unique peptidomimetics integrating heterocyclic, lipidic, and sugar moieties.

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This study developed a palladium-catalyzed, enantioselective three-component synthesis of -arylamines with high yields and enantioselectivities, providing a simple and efficient method for chiral -arylamine

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This organocascade quadruple reaction efficiently synthesizes functionalized spiropolycyclic scaffolds with high chemical yields and excellent stereoselectivity, enabling the synthesis of complex organic compounds.

Citations

Oxidative Radical Transnitrilation of Arylboronic Acids with Trityl Isocyanide.

This study demonstrates that arylboronic acids can undergo radical transnitrilation with trityl isocyanide in the presence of manganese(III) acetate, with benzoic acid showing a positive effect.

Use of convertible isocyanides for the synthesis of benazepril hydrochloride

This study presents a novel and efficient synthesis of benazepril hydrochloride in trifluoroethanol using an Ugi three-component reaction, resulting in shorter reaction times and a potent angiotensin-converting enzyme inhibitor.

α-Aminoazoles/azines: key reaction partners for multicomponent reactions

-aminoazoles/azines are key reaction partners in multicomponent reactions, enabling the synthesis of diverse structurally diverse derivatives in a single operation, reducing harmful organic waste.

An acid-catalyzed 1,4-addition isocyanide-based multicomponent reaction in neat water

This green 1,4-addition isocyanide-based three-component reaction efficiently synthesizes complex chromanones in a one-pot, environmentally friendly manner without a metal catalyst.

Microwave-assisted efficient and facile synthesis of tetramic acid derivatives via a one-pot post-Ugi cascade reaction

This microwave-assisted method efficiently synthesizes tetramic acid derivatives in good yields, offering a broad scope for producing tetramic acid analogues not easily accessible through classic synthetic methods.