Multicomponent reactions as versatile tool: development of a mild approach to 1, 3-benzothiazine-2-thiones. Issue 43 (28th October 2015)

• Record Type: Journal Article
• Authors: Stalling, Timo; Pauly, Jan; Kröger, Denis; Martens, Jürgen
• Is Part Of: Tetrahedron. Volume 71:Issue 43(2015)
• Page Start: 8290
• Page End: 8301
• Publication Date: 2015-10-28
• Subjects: Multicomponent reactions -- Heterocycles -- Carbon disulfide -- Cyclizations -- Polycyclic compounds; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2015.08.073
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: A convenient multicomponent reaction for the synthesis of a variety of rarely investigated 1, 3-benzothiazine-2-thiones using carbon disulfide, primary amines and ortho -halogenated benzaldehydes as commercially available substrates is reported. Additionally, the high performance of the newly developed one-pot procedure enables a direct route to a wide range of analog annulated polyheterocyclic structures. The potential of these compounds for the late-stage elaboration of high-functionalized molecules by simple synthetic operations is demonstrated in selected subsequent derivatizations giving heterocyclic products of high diversity. Graphical abstract: