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Organobase-catalyzed one-pot three-component synthesis of novel pyrano[2,3-d][1,3]thiazolo[3,2-a]pyrimidine derivatives

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Abstract

An efficient, simple and fast procedure has been developed for the synthesis of a novel types of pyrano[2,3-d][1,3]thiazolo[3,2-a]pyrimidine derivatives through the one-pot three-component condensation reaction of 7-hydroxy-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-5-one, malononitrile and aromatic aldehydes in the presence DIPEA (N,N-diisopropylethylamine) as an available organo-base catalyst. This proposed procedure leads to the synthesis of desired products in short reaction times (5–10 min) and excellent isolated yields (90–94%).

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Acknowledgements

We gratefully acknowledge financial support from the Research Council of the Ferdowsi University of Mashhad and Research Council of the University of Birjand.

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Authors and Affiliations

  1. Department of Chemistry, Ferdowsi University of Mashhad, Mashhad, Iran

    Abbas Ali Esmaeili, Mahdieh Zangouei & Amir Khojastehnezhad

  2. Department of Chemistry, University of Birjand, P. O. Box 97175/615, Birjand, Iran

    Fariba Mesbah, Saeid Amini-Ghalandarabad & Masoud Tasmimi

  3. Faculty of Chemistry, Kharazmi University, No. 43 Mofateh Street, Enghelab Ave, 15719-14911, Tehran, Iran

    Azizollah Habibi

  4. Faculty of Chemistry, Shahid Beheshti University, G. C., P.O. Box 1983963113, Evin, Tehran, Iran

    Ali Reza Fakhari

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  1. Abbas Ali Esmaeili
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Esmaeili, A.A., Mesbah, F., Zangouei, M. et al. Organobase-catalyzed one-pot three-component synthesis of novel pyrano[2,3-d][1,3]thiazolo[3,2-a]pyrimidine derivatives. Res Chem Intermed 47, 3537–3550 (2021). https://doi.org/10.1007/s11164-021-04477-9

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