The Chemistry of Isocyanides, Their Multicomponent Reactions and Their Libraries

Ugi, lvar; Werner, Birgit; Doemling, Alexander

doi:10.1002/chin.200409275

Cited by 23 publications

(27 citation statements)

References 22 publications

(22 reference statements)

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“…The multicomponent reaction (MCR) is a significant subclass of tandem reactions, which must be considered as a favorable green chemistry procedure because at least three or more components react to directly yield a unique product, incorporating the atoms of the starting materials with great atomic efficiency [19]. In other words, MCRs are highly flexible, chemoselective, convergent, and atom-efficient processes of high exploratory influence [20][21][22]. It is important to note that it is not necessary to isolate the reaction intermediates, making the complete procedure sustainable.…”

Section: Introductionmentioning

confidence: 99%

A Green Approach to the Production of Hybrid Diindolylmethane-Phenylboronic Acids via a 3MCR: Promising Antineoplasic Molecules

Juarez

Martínez

Córdova

et al. 2013

Journal of Chemistry

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The current role of the “Green Chemistry Protocol” in multicomponent reactions is first highlighted. Then, the green approach to the production of three novel hybrid diindolylmethanes-phenylboronic acids via a 3MCR is discussed, which features the following: solventless conditions, the use of microwave irradiation to activate the reactions, the absence of catalyst, and an efficient atom economy. The products were achieved with moderate yields (41–61%) within a short time frame (5 min) and appropriately characterized by elemental analysis and spectroscopic methods (NMR:1H,13C,11B; MS: EI, CI, FAB+, HRMS). During the FAB+MS determinations, various artifacts that are associated with the boron atom via an interaction with thioglycerol from the matrix were noted in the corresponding FAB+mass spectra; in addition, the accurate mass determination of these adducts unequivocally confirmed the presence of the target molecules. Moreover, the activity of these target molecules was evaluated in the presence of six cancer cell lines (U251 = glia of the central nerve system, PC-3 = prostate, K562 = leukemia, HCT-15 = colon, MCF-7 = breast, and SKLU-1 = lung), which resulted in themeta-regioisomer being the most active. Finally, the products were also analyzed using computational chemistry in order to determine their most stable geometries and reactivities by computing the respective molecular electrostatic potentials.

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Section: Introductionmentioning

confidence: 99%

A Green Approach to the Production of Hybrid Diindolylmethane-Phenylboronic Acids via a 3MCR: Promising Antineoplasic Molecules

Juarez

Martínez

Córdova

et al. 2013

Journal of Chemistry

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“…Hydrolysis of the imine compound 32 afforded pyruvic acid ( 23 ). The preparation of 13 C-labeled pyruvic acid ( 23 ) at any position and combinations of positions is possible via 13 C-labeled isocyanides 28 [62,63]. 13 C-Labeled isocyanides 28 are easily accessible via dehydration of formylamines.…”

Section: Synthesis Of 22 Amino Acidsmentioning

confidence: 99%

Access to Any Site Directed Stable Isotope (2H, 13C, 15N, 17O and 18O) in Genetically Encoded Amino Acids

Dawadi

Lugtenburg

2013

Molecules

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Proteins and peptides play a preeminent role in the processes of living cells. The only way to study structure-function relationships of a protein at the atomic level without any perturbation is by using non-invasive isotope sensitive techniques with site-directed stable isotope incorporation at a predetermined amino acid residue in the protein chain. The method can be extended to study the protein chain tagged with stable isotope enriched amino acid residues at any position or combinations of positions in the system. In order to access these studies synthetic methods to prepare any possible isotopologue and isotopomer of the 22 genetically encoded amino acids have to be available. In this paper the synthetic schemes and the stable isotope enriched building blocks that are available via commercially available stable isotope enriched starting materials are described.

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“…Moreover isocyanide-based multicomponent reactions (IMCRs) by virtue of their synthetic potential, convergent nature and molecular diversity have attracted much attention because of the advantages that they offer in the field of combinatorial chemistry [21][22][23]. Scheme 1.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of functionalized dihydropyrimidinones via one-pot isocyanide-based three-component reaction of N-formyl urea and dialkyl ACETYLENEDICARBOXYLATES

Naderi¹,

Mohtat²

2017

Bull. Chem. Soc. Eth.

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The Chemistry of Isocyanides, Their Multicomponent Reactions and Their Libraries

Abstract: Organic chemistryOrganic chemistry Z 0200The Chemistry of Isocyanides, Their Multicomponent Reactions and Their Libraries -[120 refs.]. -(UGI, L.; WERNER, B.; DOEMLING, A.; Molecules 8 (2003) 1, 53-66; Inst. Org. Chem.

Cited by 23 publications

References 22 publications

A Green Approach to the Production of Hybrid Diindolylmethane-Phenylboronic Acids via a 3MCR: Promising Antineoplasic Molecules

A Green Approach to the Production of Hybrid Diindolylmethane-Phenylboronic Acids via a 3MCR: Promising Antineoplasic Molecules

Access to Any Site Directed Stable Isotope (2H, 13C, 15N, 17O and 18O) in Genetically Encoded Amino Acids

Synthesis and characterization of functionalized dihydropyrimidinones via one-pot isocyanide-based three-component reaction of N-formyl urea and dialkyl ACETYLENEDICARBOXYLATES

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