Unique Structures Generated by Ugi 3CC Reactions Using Bifunctional Starting Materials Containing Aldehyde and Carboxylic Acid

Zhang, Jundong; Jacobson, Alec; Rusche, James R.; Herlihy, Walter C.

doi:10.1021/jo982192a

Cited by 86 publications

(30 citation statements)

References 13 publications

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“…Chem company Repligen have described many heterocyclic analogues, for example 257 ± 259, which contain exactly that lactam motif. [216] Piperazines such as 266 and their seven-membered analogues (e. g. 267) can be synthesized from monoalkylated (-arylated) ethylenediamines and propylenediamines, chloroacetaldehyde, carboxylic acids, and isocyanides in one step and with great diversity. Piperazine-2-carboxamides are the central elements of many drugs.…”

Section: Multicomponent Reactions With Isocyanidesmentioning

confidence: 99%

Multicomponent Reactions with Isocyanides

Dömling

Ugi

2000

Angew. Chem. Int. Ed.

3,971

1,635

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Multicomponent reactions (MCRs) are fundamentally different from two‐component reactions in several aspects. Among the MCRs, those with isocyanides have developed into popular organic‐chemical reactions in the pharmaceutical industry for the preparation of compound libraries of low‐molecular druglike compounds. With a small set of starting materials, very large libraries can be built up within a short time, which can then be used for research on medicinal substances. Due to the intensive research of the last few years, many new backbone types have become accessible. MCRs are also increasingly being employed in the total synthesis of natural products. MCRs and especially MCRs with isocyanides offer many opportunities to attain new reactions and basic structures. However, this requires that the chemist learns the “language” of MCRs, something that this review wishes to stimulate.

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Section: Multicomponent Reactions With Isocyanidesmentioning

confidence: 99%

Multicomponent Reactions with Isocyanides

Dömling

Ugi

2000

Angew. Chem. Int. Ed.

3,971

1,635

View full text Add to dashboard Cite

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“…12 These reactions were unsuccessful at high temperature, but the multicomponent reaction products 12-14 were obtained in moderate yield on stirring the reactions for prolonged periods at room temperature.…”

Section: Methodsmentioning

confidence: 99%

Isocyanide based multicomponent reactions of oxazolidines and related systems

et al. 2010

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-N-Alkyloxazolidines react in a multicomponent reaction with carboxylic acids and isocyanides to give N-acyloxyethylamino acid amides. The previously reported reaction conditions were improved using a design of experiments approach (DoE). Under the optimized conditions, good yields of the N-acyloxyethylamino acid amide products are obtained both via a three or four component approach from N-alkylethanolamines, aldehydes/ketones, isocyanides and carboxylic acids. The reaction of oxazolidines without a nitrogen substituent was found to give either the expected Ugi products or the N-acyloxyethylamino acid amides depending on the choice of reaction conditions. Optimised reaction conditions were also developed for the ring-expansion of oxazolidines to morpholin-2-ones via reaction with an isocyanide followed by hydrolysis. The mechanistic pathway of the multicomponent reaction was briefly investigated using an 18 O labelling experiment. The carboxylic acid component can be replaced by a range of other acidic nucleophiles including thiobenzoic acid, thiophenol or 5-phenyl tetrazole, which are incorporated via an alternative pathway. These latter reactions can also be applied to 2-aminotetrahydrofurans, 2-aminotetrahydropyrans or 4-hydroxybut-2-one, further extending the structural diversity of the multicomponent reaction products.

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“…The Reaction of bifunctional starting materials, such as 2-(2-formylphenoxy)acetic acid or levulinic acid containing either an aldehyde or a ketone and carboxylic acid functional groups in Ugi three-component condensation (3CC) reactions to lactam structures has been previously reported [21,22]. These results prompted us to explore the 3CC of primary amines, and isocyanides with a bifunctional starting material, containing aldehyde and hydroxy functional groups.…”

Section: Introductionmentioning

confidence: 99%