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One-pot synthesis of novel 1-(1H-tetrazol-5-yl)-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine derivatives via an Ugi-azide 4CR process

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Abstract

A facile one-pot method has been developed for the synthesis of novel pyrrolo[2,1-a]pyrazine scaffolds. A variety of 1-(1H-tetrazol-5-yl)-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine derivatives were obtained in moderate to high yields in methanol using a one-pot four-component condensation of 1-(2-bromoethyl)-1H-pyrrole-2-carbaldehyde, amine, isocyanide and sodium azide at room temperature. These reactions presumably proceed via a domino imine formation, intramolecular annulation and Ugi-azide reaction. Unambiguous assignment of the molecular structures was carried out by single-crystal X-ray diffraction.

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Acknowledgements

We acknowledge the University of Tehran for financial support of this research.

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  1. School of Chemistry, College of Science, University of Tehran, P.O. Box 14155 6455, Tehran, Iran

    Mehdi Ghandi, Saleh Salahi, Abuzar Taheri & Alireza Abbasi

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  1. Mehdi Ghandi
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Ghandi, M., Salahi, S., Taheri, A. et al. One-pot synthesis of novel 1-(1H-tetrazol-5-yl)-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine derivatives via an Ugi-azide 4CR process. Mol Divers 22, 291–303 (2018). https://doi.org/10.1007/s11030-017-9801-4

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