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. 2018 Feb 28;8(16):8961-8964.
doi: 10.1039/c8ra00326b. eCollection 2018 Feb 23.

A base promoted one pot solvent free version of the Ramachary reductive coupling/alkylation reaction for the synthesis of 2,2-disubstituted ethyl cyanoacetates

Guangyou Jiang  1 , Min Liu  1 , Dongmei Fang  2 , Ping Tan  1 , Min Huang  1 , Taiping Zhou  1 , Zhenju Jiang  1 , Zhihong Xu  1 , Zhouyu Wang  1
Affiliations

A base promoted one pot solvent free version of the Ramachary reductive coupling/alkylation reaction for the synthesis of 2,2-disubstituted ethyl cyanoacetates

Guangyou Jiang et al. RSC Adv. .

Abstract

An N,N-diisopropylethylamine promoted solvent-free Ramachary reductive coupling/alkylation (RRC/A) reaction for the synthesis of 2,2-disubstituted ethyl cyanoacetates has been developed. A series of 2,2-disubstituted ethyl cyanoacetates were synthesized in one pot by the RRC/A reaction of commercially available aldehydes, ethyl cyanacetates, alkyl halides and Hantzsch ester. A solvent free two step multicomponent reaction has also been developed for the preparation of 2,2-dialkylated malononitriles and 2,2-dialkylated 4-nitrophenyl acetonitriles. All the designed RRC/A products could be easily obtained with good yields by these methods.

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Conflict of interest statement

There are no conflicts to declare.

Figures

Fig. 1
Fig. 1. Transformations of nitriles.
Scheme 1
Scheme 1. Methods for the preparation of 2,2,2-trisubstituted nitriles.
Fig. 2
Fig. 2. Substrate scope of the solvent-free one-pot four components reaction.
Scheme 2
Scheme 2. Solvent-free one-pot two step RRC/A reaction.
See this image and copyright information in PMC

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References

    1. Fleming F. F. Nat. Prod. Rep. 1999;16:597–606. doi: 10.1039/A804370A. - DOI
    1. Fleming F. F. Yao L. Ravikumar P. C. Funk L. Shook B. C. J. Med. Chem. 2010;53:7902–7917. doi: 10.1021/jm100762r. - DOI - PMC - PubMed
    1. Lopez R. Palomo C. Angew. Chem., Int. Ed. 2015;54:13170–13184. doi: 10.1002/anie.201502493. - DOI - PubMed
    1. Fleming F. Wang Q. Chem. Rev. 2003;103:2035–2077. doi: 10.1021/cr020045d. - DOI - PubMed
    1. Guyon C. Duclos M. C. Sutter M. Metay E. Lemaire M. Org. Biomol. Chem. 2015;13:7067–7075. - PubMed