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Issue 9, 2019
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A metal- and base-free domino protocol for the synthesis of 1,3-benzoselenazines, 1,3-benzothiazines and related scaffolds

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Abstract

Efficient protocols have been described for the synthesis of 1,3-benzoselenazines, 1,3-benzothiazines, 2-aryl thiazin-4-ones and diaryl[b,f][1,5]diazocine-6,12(5H,11H)-diones. These transformations were successfully driven towards the product formation under mild acid catalyzed reaction conditions at room temperature using 2-amino aryl/hetero-aryl alkyl alcohols and amides as substrates. The merits of the present methods also rely on the easy access of rarely explored bioactive scaffolds like 1,3-benzoselenazine derivatives, for which well-documented methods are rarely known in the literature. A broad range of substrates with both electron-rich and electron-deficient groups were well-tolerated under the developed conditions to furnish the desired products in yields up to 98%. The scope of the devised method is not only restricted to the synthesis of 1,3-benzoselenazines, but it was also further extended towards the synthesis of 1,3-benzothiazines, 1,3-benzothiazinones and the corresponding eight membered N-heterocycles such as diaryl[b,f][1,5]diazocine-6,12(5H,11H)-diones.

Graphical abstract: A metal- and base-free domino protocol for the synthesis of 1,3-benzoselenazines, 1,3-benzothiazines and related scaffolds

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Publication details

The article was received on 08 Dec 2018, accepted on 24 Jan 2019 and first published on 25 Jan 2019


Article type: Paper
DOI: 10.1039/C8OB03058H
Citation: Org. Biomol. Chem., 2019,17, 2516-2528

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    A metal- and base-free domino protocol for the synthesis of 1,3-benzoselenazines, 1,3-benzothiazines and related scaffolds

    V. P. R. K. Putta, R. Gujjarappa, U. Tyagi, P. P. Pujar and C. C. Malakar, Org. Biomol. Chem., 2019, 17, 2516
    DOI: 10.1039/C8OB03058H

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