Novel applications of carbon dioxide/MeOH for the synthesis of hydantoins and cyclic ureas via the Ugi reaction

Hulme, Christopher; Ma, Liang; Romano, Joseph J.; Morton, George; Tang, Sheng Yuh; Cherrier, Marie Pierre; Choi, Steve K.; Salvino, Joseph M.; Labaudinière, Richard

doi:10.1016/s0040-4039(00)00053-8

Cited by 75 publications

(46 citation statements)

References 26 publications

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“…The intermediate 2, 3-diaminobenzofuran (269) finally reacts with a further equivalent of salicylaldehyde to the Schiff base (270). [220] Anilines (271), isocyanides (60), and aldehydes (272) react to form 3-aminoindoles (273). Interestingly, the acidic function here is the CH-acidic ortho-CH group in the aniline.…”

Section: Multicomponent Reactions With Isocyanidesmentioning

confidence: 99%

Multicomponent Reactions with Isocyanides

Dömling

Ugi

2000

Angew. Chem. Int. Ed.

3,997

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.

3,997

1,635

View full text Add to dashboard Cite

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“…Similarly, BOC protected ethylene diamines and mono-N -BOC protected phenylene diamines afford ketopiperazines [79] 128 and dihydroquinoxalinones 127 respectively [80]. Both monocyclic lactams 129 (from N-BOC-β-amino aldehydes) and bicyclic lactams 130, where post-condensation modification occurs after a tethered input has been used for the Ugi reaction, are also readily accessible [81]. If no internal nucleophile is present, the munchnone may still be trapped by an external dipolarophile to yield polysubstituted pyrroles 131, albeit in modest yields [82].…”

Section: Udc (Ugi/de-boc/cyclize) Methodologymentioning

confidence: 99%

“…Thus, workers at Rhône-Poulenc Rorer employed the CO 2 /MeOH reagent combination (MeOCO 2 H), coupled with a UDC strategy to access a variety of biologically important heterocycles [92]. Named the Ugi-5CR, this modification of the Ugi reaction was originally reported in 1961 and only two further reports of this reaction have appeared since that date [93].…”

Section: Udc (Ugi/de-boc/cyclize) Methodologymentioning

confidence: 99%

“Multi-component Reactions : Emerging Chemistry in Drug Discovery” ‘From Xylocain to Crixivan’

Hulme

Gore

2003

CMC

Self Cite

1,004

276

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With the recent emergence of combinatorial chemistry and high-speed parallel synthesis for drug discovery applications, the multi-component reaction (MCR) has seen a resurgence of interest. Easily automated one-pot reactions, such as the Ugi and Passerini reactions, are powerful tools for producing diverse arrays of compounds, often in one step and high yield. Despite this synthetic potential, the Ugi reaction is limited by producing products that are flexible and peptide-like, often being classified as 'non drug-like'. This review details developments of new, highly atom-economic MCR derived chemical methods, which enable the fast and efficient production of chemical libraries comprised of a variety of biologically relevant templates. Representative examples will also be given demonstrating the successful impact of MCR combinatorial methods at different stages of the lead discovery, lead optimization and pre-clinical process development arenas. This will include applications spanning biological tools, natural products and natural product-like diversity, traditional small molecule and 'biotech' therapeutics respectively. In particular, this review will focus on applications of isocyanide based MCR (IMCR) reactions.

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“…By varying the reaction conditions, the corresponding polyamides bearing methyl carbamate sidechains showed remarkable M n values of 20.2 kDa with polydispersity of 1.71. Encouraged by the formation of hydantoin by the methyl carbamate derivatives [94], the polymer was further converted into polyhydantoin in a very straightforward fashion. Scheme 24 Synthesis of functional P4HB by Passerini MCP and subsequent hydrogenation [90].…”

Section: Ugi Four-component Reactionmentioning

confidence: 99%

Application of named reactions in polymer synthesis

Jiang

Feng

et al. 2015

Sci. China Chem.

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In recent years, with the rapid development of polymer science, the application of classical named reactions has transferred from small-molecule compounds to polymers. The versatility of named reactions in terms of monomer selection, solvent environment, reaction temperature, and post-modification permits the synthesis of sophisticated macromolecular structures under conditions where other reaction processes will not operate. In this review, we divided the named reactions employed in polymer-chain synthesis into three types: transition metal-catalyzed cross-coupling reactions, metal-free cross-coupling reactions, and multi-components reactions. Thus, we focused our discussion on the progress in the utilization of these named reactions in polymer synthesis.

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Novel applications of carbon dioxide/MeOH for the synthesis of hydantoins and cyclic ureas via the Ugi reaction

Cited by 75 publications

References 26 publications

Multicomponent Reactions with Isocyanides

Multicomponent Reactions with Isocyanides

“Multi-component Reactions : Emerging Chemistry in Drug Discovery” ‘From Xylocain to Crixivan’

Application of named reactions in polymer synthesis

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Novel applications of carbon dioxide/MeOH for the synthesis of hydantoins and cyclic ureas via the Ugi reaction

Cited by 75 publications

References 26 publications

Multicomponent Reactions with Isocyanides

Multicomponent Reactions with Isocyanides

&#x201C;Multi-component Reactions : Emerging Chemistry in Drug Discovery&#x201D; &#x2018;From Xylocain to Crixivan&#x2019;

Application of named reactions in polymer synthesis

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“Multi-component Reactions : Emerging Chemistry in Drug Discovery” ‘From Xylocain to Crixivan’