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Umpolung cyclization reaction of N-cinnamoylthioureas in the presence of DBU

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Abstract

A novel regioselective cyclization reaction of N-cinnamoylthioureas leading to six- or five-membered heterocyclic compounds was developed. N-Cinnamoylthioureas in the presence of trifluoroacetic acid (TFA) underwent the well-established intramolecular cycloaddition reaction to give 2-imino-2,3,5,6-tetrahydro-4H-1,3-thiazin-4-ones in good yields. On the other hand, the reaction with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) proceeded in an unprecedented “umpolung” cyclization fashion to afford five-membered 2-imino-1,3-thiazolidin-4-ones and/or 2-thioxoimidazolidine-4-ones. The reaction was considered to occur via a cycloadduct of DBU with the cinnamoyl moiety followed by intramolecular attack of the thiourea group.

Graphical abstract: Umpolung cyclization reaction of N-cinnamoylthioureas in the presence of DBU

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Publication details

The article was received on 23 Aug 2018, accepted on 03 Oct 2018 and first published on 04 Oct 2018


Article type: Paper
DOI: 10.1039/C8OB02066C
Citation: Org. Biomol. Chem., 2018, Advance Article
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    Umpolung cyclization reaction of N-cinnamoylthioureas in the presence of DBU

    R. Saito, N. Uemura, H. Ishikawa, A. Magara, Y. Yoshida, T. Mino, Y. Kasashima and M. Sakamoto, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C8OB02066C

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