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Three-component reaction between amines, carbon disulfide and electron-deficient derivatives of chloropyridine or chlorobenzene: synthesis of 3,6-diazaspiro[4.5]deca-2,7,9-trien-6-ium chloride and dithioylcarbamates derivatives

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Abstract

In this study, three-component reaction of some primary and secondary amines with carbon disulfide in the presence of electron-deficient derivatives of chloropyridine or chlorobenzene in the CH3CN as a solvent is reported. The reaction of primary amines with carbon disulfide and electron-deficient compounds of chloropyridine or chlorobenzene after 6–8 h afforded the three-component addition product. The reaction of secondary amines with carbon disulfide and electron-deficient compounds of chloropyridine or chlorobenzene after 3–4 h afforded the two-component addition product. The product(s) of reactions were purified by recrystallization or column chromatography and their structures were identified by spectroscopy techniques such as 1H-NMR, 13C-NMR, IR, UV and elemental analysis. The reactions were carried out under mild conditions and without using a catalyst.

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Acknowledgments

The authors wish to thank Rafsanjan Vali-e-Asr University (Rafsanjan, Iran) for the partial support of this work.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Vali-e-Asr University, 77176, Rafsanjan, Islamic Republic of Iran

    Reza Ranjbar-Karimi, Aliyeh Khajeh-Khezri & Mohammad Anary-Abbasinejad

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  1. Reza Ranjbar-Karimi
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  2. Aliyeh Khajeh-Khezri
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  3. Mohammad Anary-Abbasinejad
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Correspondence to Reza Ranjbar-Karimi.

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Ranjbar-Karimi, R., Khajeh-Khezri, A. & Anary-Abbasinejad, M. Three-component reaction between amines, carbon disulfide and electron-deficient derivatives of chloropyridine or chlorobenzene: synthesis of 3,6-diazaspiro[4.5]deca-2,7,9-trien-6-ium chloride and dithioylcarbamates derivatives. J IRAN CHEM SOC 11, 289–295 (2014). https://doi.org/10.1007/s13738-013-0300-y

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  • DOI: https://doi.org/10.1007/s13738-013-0300-y

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