Direct Access to Heterocyclic Scaffolds by New Multicomponent Ugi−Smiles Couplings

Kaim, Laurent El; Gizolme, Marie; Grimaud, Laurence; Oble, Julie

doi:10.1021/ol061605o

Cited by 79 publications

(25 citation statements)

References 18 publications

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“…56 As already mentioned, the presence of a nitrogen atom in the aromatic system decreases the electron density on the aromatic carbon atoms. 56 As already mentioned, the presence of a nitrogen atom in the aromatic system decreases the electron density on the aromatic carbon atoms.…”

Section: Ugi-smiles Couplingsmentioning

confidence: 91%

Smiles Rearrangements

Kaim

Grimaud

2015

Molecular Rearrangements in Organic Synthesis

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Section: Ugi-smiles Couplingsmentioning

confidence: 91%

Smiles Rearrangements

Kaim

Grimaud

2015

Molecular Rearrangements in Organic Synthesis

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“…Excess solvent was removed under reduced pressure and the crude product was purified by column chromatography (2:1 Petrol:EtOAc) to yield 23 (660 mg, 90 %) as colourless needles; R f 0. 16 N-tert-Butyl-5-(5-phenyl-2H-tetrazol-2-yl)-2-(pyrrolidin-1-yl) pentanamide 29a and N-tert-butyl-5-(5-phenyl-1H-tetrazol-1-yl)-2-(pyrrolidin-1-yl) 3.6.8. N-tert-Butyl-2-morpholino-6-(5-phenyl-2H-tetrazol-2-yl)hexanamide 30a (major) and N-tert-butyl-2-morpholino-6-(5-phenyl-1H-tetrazol-1-yl)hexanamide 30b (minor), (10:1 Mixture).…”

Section: N-(tert-butylcarbamoyl-p-tolylmethyl)-n-(2-hydroxyethyl)benzmentioning

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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“…Subsequent trapping of the nitrilium intermediate by carboxylate followed by the irreversible acyl transfer step, known as the Mumm rearrangement [14], associated with the Ugi reaction seems to be responsible for the displacement of various equilibria. In a recently disclosed novel Ugi-type process, phenols have been used instead of carboxylic acids [15][16][17][18][19][20]. These reactions involve an irreversible Smiles rearrangement in place of the traditional Mumm acyl transfer.…”

Section: Introductionmentioning

confidence: 99%