Diastereoselective Synthesis of some pyrrolidin-2-ones azasugars and study of their stereochemistry
DOI:
https://doi.org/10.13171/mjc8119021922cbAbstract
The microwave-promoted one-pot multicomponent synthesis of substituted pyrrolidinols using a bifunctional sugar-derived hydroxy-[gamma]-lactone component of amine component or cyanide group is reported. Clean reaction profile, easy work-up procedure, excellent yields and short reaction times are some remarkable features of this method.This modular approach features the in situ-generation of iminium ions intermediate that allows the diastereoselective assembly of the diverse pyrrolidinones efficiently under microwave irradiation has been used.References
- T. J. J. M üller. General Discussion and Reactions Involving a Carbonyl Compound as Electrophilic Component. In: T. J. J. M üller., editor. Multicomponent Reactions 1. Stuttgart: Georg Thieme Verlag KG, 2014. pp. 5-27. (Science of Synthesis Series).
- D.M. D'Souza, T. J.J. M üller, Multi-component syntheses of heterocycles by transition-metal catalysis Chem. Soc. Rev, 2007, 36, 1095-1108.
- H. Ahankar, A. Ramazani, K.Slepokura, T. Lis, S-W. Joo, Synthesis of pyrrolidinone derivatives from aniline, an aldehyde and diethyl acetylenedicarboxylate in an ethanolic citric acid solution under ultrasound irradiation, Green Chem, 2016, 18, 3582-3593.
- B. Winbal. Piracetam, A review of pharmacological properties and clinical uses. CNS Drug Rev. 2005, 11, 169-182.
- P. Singh, V. Dimitriou, R. P. Malajan, A.W. Crossley, Double-blind comparison between doxapram and pethidine in the treatment of postanaesthetic shivering. Br. J. Anaesth. 1993, 71, 685-688.
- M. S. F. Franco, G. A. Casagrande. C. Raminelli, S. Moura, M. Rossatto, F.H. Quina, L. Pizzuti, Ultrasound-Promoted Environmentally Friendly Synthesis of 5-(3,3,3- Trifluoro-2-oxopropylidene) pyrrolidin-2- ones, Synth. Commun, 2015, 45, 692-701.
- M. B-Brlek, M. Meanwel, R. Britton, Direct synthesis of imino-C-nucleoside analogues and other biologically active iminosugars, Nature Communications, 2015, 1-6
- S. Mukhopadhyay, S. Chandra Pan, Organocatalytic asymmetric synthesis of highly
substituted pyrrolidines bearing a stereogenic quaternary centre at the 3-position, Org. Biomol. Chem., 2018, 16, 9349-9353
- Q. Zhu, H. Jian, J. Li, Liu. Sh.Ch. XiaM. Zhang, Concise and Versatile Multicomponent Synthesis of Multisubstituted Polyfunctional Dihydropyrroles, J. Comb. Chem, 2009, 11, 685-696.
- A. Loupy, Microwaves in Organic Synthesis; Wiley-VCH, Weinheim; second Ed, 2006.
- P. Compain, V. Chagnault, O.R. Martin, Tactics and strategies for the synthesis of iminosugar C-glycosides: a review, Tetrahedron Asymmetry, 2009, 20, 672
- D. Declerck, S. Josse, A. Van. NhienNguen, D. Postel, Synthesis of 2-Aminocyclopropyl Pyrrolidines from Glycoaminonitriles, Tetrahedron. Lett, 2009, 2171-2173.
- R.D. Borcherdinf, A. S. Scholtz, T. R. Borchard. “Synthesis of analogues of neplanocin A: utilization of optically active
dihydroxycyclopentenones derived from carbohydrates, Journal of Organic Chemistry, 1987, 52, 5457-5461,
- X. Zhou, W.J. Liu, L. P. Ye J. Q. Huang, A versatile approach to pyrrolidine azasugars and homoazasugars based on a highly diastereoselective reductive benzyloxymethylation of protected tartarimide Tetrahedron, 63, 2007, 6346-6357.
- J.T. Pinhey, S. Sternhell, Aust. J. Chem., 1985, 38, 1155-1161.
Downloads
Published
Issue
Section
License
Authors who publish with this journal agree to the following terms:- Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution License that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal
- Authors are able to enter into separate, additional contractual arrangements for the non-exclusive distribution of the journal's published version of the work (e.g., post it to an institutional repository or publish it in a book), with an acknowledgement of its initial publication in this journal
- Authors are permitted and encouraged to post their work online (e.g., in institutional repositories or on their website) prior to and during the submission process, as it can lead to productive exchanges, as well as earlier and greater citation of published work (See The Effect of Open Access).