A facile synthesis of N-carbamoylmethyl- α -aminobutyrolactones by the Ugi multicomponent condensation reaction

Park, Soo Jung; Keum, Gyochang; Kang, Seonmi; Koh, Hun Yeong; Kim, Youseung; Lee, Duck‐Hyung

doi:10.1016/s0040-4039(98)01509-3

Cited by 80 publications

(38 citation statements)

References 23 publications

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“…[182] Whereas serine and threonine are transformed intermolecularly to the corresponding iminodicarboxylic acid derivatives without participation of the hydroxy function, homoserine (199) as the a-amino acid component leads to the a-amino-g-lactam 200 in the solvent trifluoroethanol. [183] Hundreds of potential virostatics, for example 203, were synthesized with nucleobase-derived aldehydes (201), a-amino acids (193), and isocyanides (202), and screened for their activity. [184] The methods impress with their simplicity: After the insoluble a-amino acid is dissolved through the reaction with aldehyde and isocyanide in alcohol, the conversion is finished and surplus solvent is removed.…”

Section: Reviewsmentioning

confidence: 99%

Multicomponent Reactions with Isocyanides

Dömling

Ugi

2000

Angew. Chem. Int. Ed.

3,969

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: Reviewsmentioning

confidence: 99%

Multicomponent Reactions with Isocyanides

Dömling

Ugi

2000

Angew. Chem. Int. Ed.

3,969

1,635

View full text Add to dashboard Cite

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“…The reaction with homoserine (Scheme 41, X = O, n = 1) gave the corresponding lactones 87 in excellent yields and diastereoselectivities. [150] This reaction can be expanded to lysine (Scheme 41, X = NH, n = 3), giving the corresponding e-lactams 87.…”

Section: Angewandte Chemiementioning

confidence: 99%

Asymmetric Multicomponent Reactions (AMCRs): The New Frontier

2005

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Asymmetric multicomponent reactions involve the preparation of chiral compounds by the reaction of three or more reagents added simultaneously. This kind of addition and reaction has some advantages over classic divergent reaction strategies, such as lower costs, time, and energy, as well as environmentally friendlier aspects. All these advantages, together with the high level of stereoselectivity attained in some of these reactions, will force chemists in industry as in academia to adopt this new strategy of synthesis, or at least to consider it as a viable option. The positive aspects as well as the drawbacks of this strategy are discussed in this Review.

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“…Moreover, one-pot multi-component condensation reactions, due to their productivity, facile execution and simple reaction profile, are one of the important strategies in multi-component reactions, which have expanded rapidly in organic chemistry. [1][2][3][4] It is found in the recent literature that several indole derivatives are reported to possess a wide variety of biological properties, e.g. CNS depressant, 5 anti-inflammatory and analgesic, 6 antiviral, 7 anthelmintic, 8 antibacterial, 9 anticonvulsant, 10 cardiovascular, 11 and antihypertensive activity.…”

Section: Introductionmentioning

confidence: 99%