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. 2016;18(13):3718-3721.
doi: 10.1039/C6GC00910G. Epub 2016 May 19.

An Efficient Passerini Tetrazole Reaction (PT-3CR)

Affiliations

An Efficient Passerini Tetrazole Reaction (PT-3CR)

Ajay L Chandgude et al. Green Chem. 2016.

Abstract

A sonication accelerated, catalyst free, simple, high yielding and efficient method for the Passerini-type three component reaction (PT-3CR) has been developed. It comprises reaction of an aldehyde/ketone, a isocyanide and a TMS-azide in methanol:water (1:1) as the solvent system. Use of sonication not only accelerated the rate of the reaction but also provided up to quantitative yields. This reaction is applicable to a broad scope of aldehyde/ketone and isocyanides.

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Figures

Fig 1
Fig 1
Some bio-active agents/drugs containing the tetrazole moiety.
Scheme 1
Scheme 1
Synthesis of fused tetrazole.

References

    1. For a review on the importance of tetrazole derivatives, see: Wei CX, Bian M, Gong GH. Molecules. 2015;20:5528–5553. Roh J, Vavrova K, Hrabalek A. Eur. J. Org. Chem. 2012:6101–6118. Mohite PB, Bhaskar VH. Int. J. Pharm.Tech. Res. 2011;3:1557–1566. Frija LM, Ismael A, Cristiano MLS. Molecules. 2010;15:3757–3774. Myznikov LV, Hrabalek A, Koldobskii GI. Chem. Heterocycl. Compd. 2007;43:1–9.

    1. For a review on the synthesis of tetrazole derivatives, see: Malik M, Wani M, Al-Thabaiti S, Shiekh R. J Incl. Phenom. Macrocycl. Chem. 2014;78:15–37. Koldobskii GI. Russ. J. Org. Chem. 2006;42:469–486. Herr RJ. Bioorg. Med. Chem. 2002;10:3379–3393. Zubarev VY, Ostrovskii VA. Chem. Heterocycl. Compd. 2000;36:759–774. Wittenberger SJ. Org. Prep. Proced. Int. 1994;26:499–531.

    1. Sarvary A, Maleki A. Mol. Divers. 2015;19:189–212. - PubMed
    1. For a general review on the importance of MCR reactions, see: Dömling A, Wang W, Wang K. Chem. Rev. 2012;112:3083–3135. Zarganes-Tzitzikas T, Chandgude AL, Dömling A. Chem. Rec. 2015;15:981–996.

    1. Passerini M, Simone L. Gazz. Chim. Ital. 1921;51:126–129.
    2. Passerini M, Ragni G. Gazz. Chim. Ital. 1931;61:964–969.

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