Efficient access to chiral N-substituted saccharin analogues via the directed ortho-lithiation of 3-N-arylsulfonyloxazolidin-2-ones

Aliyenne, Ahmed; Jameleddine, Khiari; Kraı̈em, Jamil; Kacem, Yakdhane; Hassine, Béchir Ben

doi:10.1016/j.tetlet.2006.06.148

Cited by 23 publications

(6 citation statements)

References 28 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…The process was driven by the CIPE effect and constitutes a mild method for the LDA-HMPA mediated regiospecific conversion of N-(arylsulfonyl)oxazolidin-2-ones 125, readily available from optically pure amino acids, into novel chiral analogues of saccharins 127 via the lithiated intermediates 126 (Scheme 33). 44…”

Section: Scheme 32mentioning

confidence: 99%

Heterocycle-Mediated ortho-Functionalization of Aromatic Compounds: The DoM Methodology and Synthetic Utility

Florio

Salomone

2016

Synthesis

View full text Add to dashboard Cite

The directed ortho-lithiation of substituted aromatics containing a small-ring heterocycle as a directing metalating group is described. The reaction of the ortho-lithiated intermediates with electrophiles gives successfully the corresponding substituted derivatives. This brief review highlights the importance of heterocyclic systems as directed metalation groups (DMG) in the regioselective lithiation of simple aromatic compounds. The utility of the synthetic elaboration of the heterocyclic moiety is also stressed. It is possible to access interesting molecules by combining DoM methodology with Negishi or Suzuki-Miyaura cross-coupling protocols. 1 Introduction 2 Lithiation of Aryl-Substituted O-Heterocycles 3 Lithiation of Aryl-Substituted N-Heterocycles 4 Lithiation of Five-Membered Arylheterocycles 5 Conclusion

show abstract

Section: Scheme 32mentioning

confidence: 99%

Heterocycle-Mediated ortho-Functionalization of Aromatic Compounds: The DoM Methodology and Synthetic Utility

Florio

Salomone

2016

Synthesis

View full text Add to dashboard Cite

show abstract

“…The green chemistry concept emerged in 1990 [ 18 ] with the aim at developing cleaner approaches through the simplification of chemical processing along with the decreases of waste and cost. As a part of our ongoing efforts directed toward the development of environmentally safe conditions for the synthesis of heterocyclic compounds starting from natural (L)-α-amino acids [ 19 – 23 ] and the reactivity of α-amino acid phenylhydrazides [ 24 – 25 ], we now report a green and eco-friendly procedure for the synthesis of new chiral 1-(arylamino)-1 H -imidazo[2,1- a ]isoindole-2,5(3 H ,9b H )-diones ( Scheme 1 ).…”

Section: Introductionmentioning

confidence: 99%

Green synthesis of new chiral 1-(arylamino)imidazo[2,1-a]isoindole-2,5-diones from the corresponding α-amino acid arylhydrazides in aqueous medium

Bouzayani¹,

Kraїem²,

Marque³

et al. 2018

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

New chiral 1-(arylamino)imidazo[2,1-a]isoindole-2,5-dione derivatives were obtained in good to excellent yields via the cyclocondensation of 2-formylbenzoic acid and various α-amino acid arylhydrazides using water as the solvent in the presence of sodium dodecyl sulfate as the surfactant and under simple and minimum manipulation, without purification. The reaction is totally diastereoselective and gives access to the nitrogenated tricyclic core with a relative trans stereochemistry.

show abstract

“…Several different synthetic routes have been applied to construct the heterocyclic compound 1,2-benzisothiazol-3-one-1,1-dioxide, commonly known as saccharin ( 1 , Figure 1 ), a synthetic calorie-free sugar substitute [ 1 , 2 ]. Alkylation methods to prepare N - and O -substituted (carbonyl oxygen) derivatives of 1 are well established and these have provided researchers with the straightforward synthesis of novel and potentially bioactive molecules [ 3 , 4 , 5 , 6 ]. In addition to N - and O -alkylation, compounds derivatised on the benzene moiety of 1 are particularly desirable, as these compounds retain both the cyclic sulfonamide and lactam groups which can participate in strong noncovalent interactions with biomolecular targets such as enzymes.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Novel Saccharin Derivatives

Rankin

Poulsen

2017

Molecules

View full text Add to dashboard Cite

The synthesis of saccharin (1,2-benzisothiazol-3-one-1,1-dioxide) derivatives substituted on the benzene ring has seen limited development despite the longevity of this compound’s use as an artificial sweetener. This type of saccharin derivative would however present attractive properties for the development of new bioactive, drug-like small molecule compounds. Here we report the derivatisation of the benzene ring of saccharin using Cu(I)-catalyzed azide alkyne cycloaddition (CuAAC) to synthesise a diverse library of novel saccharin-1,2,3-triazole conjugates. All library compounds retain the capability for interactions with biomolecules via the unmodified sulfonamide and lactam groups of the parent saccharin core heterocycle. The compounds also encompass alternate orientations of the 1,2,3-triazole heterocycle, thus further adding diversity to the potential hydrogen bonding interactions of these compounds with biomolecules of therapeutic interest. Our findings demonstrate that specifically functionalized derivatives of saccharin may be prepared from either saccharin azide or saccharin alkyne building blocks in high yield using CuAAC.

show abstract

Efficient access to chiral N-substituted saccharin analogues via the directed ortho-lithiation of 3-N-arylsulfonyloxazolidin-2-ones

Cited by 23 publications

References 28 publications

Heterocycle-Mediated ortho-Functionalization of Aromatic Compounds: The DoM Methodology and Synthetic Utility

Heterocycle-Mediated ortho-Functionalization of Aromatic Compounds: The DoM Methodology and Synthetic Utility

Green synthesis of new chiral 1-(arylamino)imidazo[2,1-a]isoindole-2,5-diones from the corresponding α-amino acid arylhydrazides in aqueous medium

Synthesis of Novel Saccharin Derivatives

Contact Info

Product

Resources

About