Issue 0, 1983

Reaction between 2,2′-dithiodianiline and activated alkynes. Synthesis of 4H-1,4-benzothiazines

Abstract

By the title reaction acetylenic esters (2a–c), ketones (2d–g), and the nitrile (2h) gave in all cases the corresponding 4H-1,4-benzothiazines (3) together with other products whose nature depends on the alkyne used. Thus benzothiazoline and/or benzothiazole, benzothiazepine, and vinylsulphides were obtained in the representative cases (2c, f, h) studied in detail. Some of these latter compounds have been independently synthesised by reaction of 2-aminobenzenethiol with corresponding alkyne (2). In particular conditions by the reactions between 2,2′-dithiodianiline (1) and alkynes (2f, d) we isolated bisenamine compounds (19) and (20) respectively and their intermediacy in formation of the corresponding benzothiazines (3f) and (3d) was achieved. The mechanisms of the observed reactions are also suggested.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1983, 567-572

Reaction between 2,2′-dithiodianiline and activated alkynes. Synthesis of 4H-1,4-benzothiazines

G. Liso, G. Trapani, A. Reho, A. Latrofa and F. Loiodice, J. Chem. Soc., Perkin Trans. 1, 1983, 567 DOI: 10.1039/P19830000567

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Spotlight

Advertisements