Parallel synthesis of tandem Ugi/Diels–Alder reaction products on a soluble polymer support directed toward split-pool realization of a small molecule library

Oikawa, Masato; Ikoma, Minoru; Sasaki, Makoto

doi:10.1016/j.tetlet.2004.11.115

Cited by 34 publications

(19 citation statements)

References 24 publications

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“…The formation of a C-N bond via the intramolecular nucleophilic substitution reaction of an amino group with an aryl fluoride through pathway B leads to scaffold 3. Reactions of this type are generally conducted as the last step in the ring closing process because they are unaffected by the other transformations involved in the process [9,[12][13][14][15][16][17]. Other ring-closing procedures can also be used to promote the nucleophilic substitution reaction.…”

Section: Introductionmentioning

confidence: 99%

Facile microwave-assisted synthesis of 1H-pyrazino[1,2-a]quinoxaline-1,5(6H)-dione derivatives via a nucleophilic substitution reaction

et al. 2015

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A series of compounds containing the 1H-pyrazino[1,2-a]quinoxaline-1,5(6H)-dione scaffold have been synthesized using a one-pot procedure under microwave irradiation. This new strategy allowed for the facile synthesis of target compounds in good yields and could be readily applied to the construction of diverse libraries of compounds for high throughput screening in medicinal chemistry.nucleophilic substitution reaction, microwave, Ugi reaction, MCRs, 1H-pyrazino[1,2-a]quinoxaline-1,5(6H)-dione

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Section: Introductionmentioning

confidence: 99%

Facile microwave-assisted synthesis of 1H-pyrazino[1,2-a]quinoxaline-1,5(6H)-dione derivatives via a nucleophilic substitution reaction

et al. 2015

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“…[20] As carboxylic acid components, five fumaric acid monoamides 11-15 were prepared from commercially available monoethyl fumarate in one-pot operations involving acid chloride formation [(COCl) 2 , DMF, benzene, 0°C, 2 h, then concentration] followed by amidation and hydrolysis (RNH 2 , Cs 2 CO 3 , THF, room temp., 12 h, then KOH, H 2 O, room temp., 12 h). [21] All tandem UDA reactions were carried out by mixing equimolar amounts of the four components in MeOH and stirring at room temp. for 48 h. The reaction mixtures were then concentrated and purified to give the products 16-23 in 32-93 % yields.…”

Section: Introductionmentioning

confidence: 99%

“…for 48 h. The reaction mixtures were then concentrated and purified to give the products 16-23 in 32-93 % yields. Since the yields of the UDA reactions generally depend on the formation of the imine intermediates (the first step in the Ugi MCR), [21] the low yields observed especially in runs 1, 3, 5, and 6 should be improved by the use of large excesses (20 equiv.) [21,22] of amine, isocyanide, and carboxylic acid components relative to 2-furfural.…”

Section: Introductionmentioning

confidence: 99%

“…Since the yields of the UDA reactions generally depend on the formation of the imine intermediates (the first step in the Ugi MCR), [21] the low yields observed especially in runs 1, 3, 5, and 6 should be improved by the use of large excesses (20 equiv.) [21,22] of amine, isocyanide, and carboxylic acid components relative to 2-furfural. The structure of all products were spectroscopically determined by analogy with the authentic compounds reported previously by us.…”

Section: Introductionmentioning

confidence: 99%

“…The structure of all products were spectroscopically determined by analogy with the authentic compounds reported previously by us. [21] Scheme 4. A preliminary study for the synthesis of the F-type heterotricycle 6 from 1.…”

Section: Introductionmentioning

confidence: 99%

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Chemospecific Allylation and Domino Metathesis of 7‐Oxanorbornenes for Skeletal and Appendage Diversity

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A Half‐Century of the Ugi Reaction: Classic Variant

Ullrich

Kazmaier

2023

Organic Reactions

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The classic Ugi reaction is a four‐component coupling process that involves a carboxylic acid, a carbonyl compound, an amine, and an isocyanide. All reaction components are in a dynamic equilibrium with several intermediates, until an irreversible intramolecular 1,4‐ O → N acyl transfer leads to the formation of an N ‐acylamino acid amide. If chiral components are used in this reaction, a mixture of diastereomers is generally formed with moderate‐to‐low stereoselectivity. The broad scope of substrates that can be used in the Ugi reaction allows for the straightforward synthesis of libraries of structurally related amino acid and peptide derivatives. Therefore, this methodology is often applied to the synthesis of drugs, drug‐like molecules, and natural products. This chapter describes different variations of classic Ugi reactions, including the use of functionalized and cleavable reaction components to illustrate the broad scope of the reaction. In addition, applications in target‐directed synthesis and comparisons to other related multicomponent reactions are presented. Tabular surveys are organized according to the isocyanides used. The literature is discussed from the first disclosure of an Ugi reaction in 1961 through to the end of 2012.

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Parallel synthesis of tandem Ugi/Diels–Alder reaction products on a soluble polymer support directed toward split-pool realization of a small molecule library

Cited by 34 publications

References 24 publications

Facile microwave-assisted synthesis of 1H-pyrazino[1,2-a]quinoxaline-1,5(6H)-dione derivatives via a nucleophilic substitution reaction

Facile microwave-assisted synthesis of 1H-pyrazino[1,2-a]quinoxaline-1,5(6H)-dione derivatives via a nucleophilic substitution reaction

Chemospecific Allylation and Domino Metathesis of 7‐Oxanorbornenes for Skeletal and Appendage Diversity

A Half‐Century of the Ugi Reaction: Classic Variant

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