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Facile and efficient approach for the synthesis of spirocyclopropylbarbiturates and 3-substituted-1,1,2,2-tetracyanocyclopropanes using N-halosulfonamides

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Abstract

The applications of \(N{,}N{,}N^{\prime }{,}N^{\prime }\)-tetrabromobenzene-1,3-disulfonamide [TBBDA], poly(N-bromo-N-ethyl-benzene-1,3-disulfonamide) [PBBS], \(N{,}N{,}N^\prime {,}N^\prime \)-tetrachlorobenzene-1,3-disulfonamide [TCBDA], and poly(N-chloro-N-ethyl-benzene-1,3-disulfonamide) [PCBS] as novel reagents for the preparation of spirocyclopropylbarbiturates from 2-arylidenemalononitriles and barbituric acids are described. In addition, an effective and simple domino procedure for the synthesis of 3-substituted-1,1,2,2-tetracyanocyclopropanes from carbonyl compounds and malononitrile in a one-pot manner is reported. These reactions involve Michael addition, halogenation, and intramolecular ring-closing (MHIRC) reaction sequences.

Graphical Abstract

We have developed an efficient procedure for the synthesis of spirocyclopropylbarbiturates and 3-substituted-1,1,2,2-tetracyanocyclopropanes using TBBDA, PBBS, TCBDA, and PCBS as new reagents

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Acknowledgments

We acknowledge with thanks the financial support received from Bu-Ali Sina University, Center of Excellence and Development of Chemical Methods (CEDCM).

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Authors and Affiliations

  1. Department of Organic Chemistry, Faculty of Chemistry, Bu-Ali Sina University, Hamedan, 65174, Iran

    Ramin Ghorbani-Vaghei, Yaser Maghbooli, Azadeh Shahriari & Jafar Mahmoodi

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  1. Ramin Ghorbani-Vaghei
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  2. Yaser Maghbooli
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  3. Azadeh Shahriari
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  4. Jafar Mahmoodi
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Correspondence to Ramin Ghorbani-Vaghei.

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Ghorbani-Vaghei, R., Maghbooli, Y., Shahriari, A. et al. Facile and efficient approach for the synthesis of spirocyclopropylbarbiturates and 3-substituted-1,1,2,2-tetracyanocyclopropanes using N-halosulfonamides. Mol Divers 20, 907–917 (2016). https://doi.org/10.1007/s11030-016-9682-y

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  • DOI: https://doi.org/10.1007/s11030-016-9682-y

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