Literature DB >> 19067214

Ionic liquid promoted preparation of 4H-thiopyran and pyrimidine nucleoside-thiopyran hybrids through one-pot multi-component reaction of thioamide.

Xinying Zhang1, Xiaoyan Li, Xuesen Fan, Xia Wang, Dongfang Li, Guirong Qu, Jianji Wang.   

Abstract

One-pot multi-component reactions of aldehydes, cyanothioacetamide and malononitrile promoted by ionic liquid proved to be an efficient way for the synthesis of thiopyran derivatives. Without any added catalyst, both aromatic and aliphatic aldehydes participated in this reaction smoothly. As an application of this method, a pyrimidine nucleoside-thiopyran chimera with potential biological activities was obtained in high yield from 5-formyl-2'-deoxyuridine. In addition, the ionic liquid used can be easily recovered and effectively reused for at least 5 times.

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Year:  2008        PMID: 19067214     DOI: 10.1007/s11030-008-9098-4

Source DB:  PubMed          Journal:  Mol Divers        ISSN: 1381-1991            Impact factor:   2.943


  8 in total

1.  Thioamides as useful synthons in the synthesis of heterocycles.

Authors:  Tadeusz S Jagodziński
Journal:  Chem Rev       Date:  2003-01       Impact factor: 60.622

2.  Paradigm confirmed: the first use of ionic liquids to dramatically influence the outcome of chemical reactions.

Authors:  Martyn J Earle; Suhas P Katdare; Kenneth R Seddon
Journal:  Org Lett       Date:  2004-03-04       Impact factor: 6.005

3.  Assembling a smallpox biodefense by interrogating 5-substituted pyrimidine nucleoside chemical space.

Authors:  Xuesen Fan; Xinying Zhang; Longhu Zhou; Kathy A Keith; Earl R Kern; Paul F Torrence
Journal:  Antiviral Res       Date:  2006-05-19       Impact factor: 5.970

4.  5-(Dimethoxymethyl)-2'-deoxyuridine: a novel gem diether nucleoside with anti-orthopoxvirus activity.

Authors:  Xuesen Fan; Xinying Zhang; Longhu Zhou; Kathy A Keith; Earl R Kern; Paul F Torrence
Journal:  J Med Chem       Date:  2006-06-01       Impact factor: 7.446

5.  Toward orthopoxvirus countermeasures: a novel heteromorphic nucleoside of unusual structure.

Authors:  Xuesen Fan; Xinying Zhang; Longhu Zhou; Kathy A Keith; Mark N Prichard; Earl R Kern; Paul F Torrence
Journal:  J Med Chem       Date:  2006-07-13       Impact factor: 7.446

6.  [5C + 1S] annulation: a facile and efficient synthetic route toward functionalized 2,3-dihydrothiopyran-4-ones.

Authors:  Xihe Bi; Dewen Dong; Yan Li; Qun Liu; Qian Zhang
Journal:  J Org Chem       Date:  2005-12-23       Impact factor: 4.354

7.  A pyrimidine-pyrazolone nucleoside chimera with potent in vitro anti-orthopoxvirus activity.

Authors:  Xuesen Fan; Xinying Zhang; Longhu Zhou; Kathy A Keith; Earl R Kern; Paul F Torrence
Journal:  Bioorg Med Chem Lett       Date:  2006-04-05       Impact factor: 2.823

8.  Thiopyran route to polypropionates: an efficient synthesis of serricornin.

Authors:  Dale E Ward; Vishal Jheengut; Garrison E Beye
Journal:  J Org Chem       Date:  2006-11-10       Impact factor: 4.354

  8 in total
  5 in total

Review 1.  Structural modifications of nucleosides in ionic liquids.

Authors:  Vineet Kumar; Virinder S Parmar; Sanjay V Malhotra
Journal:  Biochimie       Date:  2010-02-21       Impact factor: 4.079

Review 2.  Recent developments in utility of green multi-component reactions for the efficient synthesis of polysubstituted pyrans, thiopyrans, pyridines, and pyrazoles.

Authors:  Mohamed Hilmy Elnagdi; Moustafa Sherief Moustafa; Saleh Mohammed Al-Mousawi; Ramadan Ahmed Mekheimer; Kamal Usef Sadek
Journal:  Mol Divers       Date:  2015-04-17       Impact factor: 2.943

3.  Expedient synthesis of novel antibacterial hydrazono-4-thiazolidinones under catalysis of a natural-based binary ionic liquid.

Authors:  Maedeh Saeedi Mirakmahaleh; Kurosh Rad-Moghadam; Hassan Kefayati; Soroush Falakro
Journal:  Mol Divers       Date:  2020-01-14       Impact factor: 2.943

4.  A novel four- and pseudo-five-component reaction: unexpected efficient one-pot synthesis of 4H-thiopyran derivatives.

Authors:  Akbar Mobinikhaledi; Mohammad Ali Bodaghifard; Sajad Asadbegi
Journal:  Mol Divers       Date:  2015-09-08       Impact factor: 2.943

Review 5.  Multicomponent reactions in nucleoside chemistry.

Authors:  Mariola Koszytkowska-Stawińska; Włodzimierz Buchowicz
Journal:  Beilstein J Org Chem       Date:  2014-07-29       Impact factor: 2.883

  5 in total

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