Regioselective synthesis of 1,3-thiazines by sequential 4-oxothiazolidine to 1,2-dithiole to 1,3-thiazine transformations: role of intramolecular non-bonded S/O interactions

Rašović, Aleksandar; Steel, Peter J.; Kleinpeter, Erich; Marković, Rade

doi:10.1016/j.tet.2006.12.075

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2007

Authors

Rašović, Aleksandar

Steel, Peter J.

Kleinpeter, Erich

Marković, Rade

Article (Published version)

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Abstract

A new synthetic approach to 2,3-dihydro-4H-1,3-thiazine derivatives based upon reductive rearrangement of 1,2-dithiole-3-ylidene thiones has been developed. In turn, the 1,2-dithiole derivatives were prepared by an efficient ring-opening-closing process of 2-alkylidene-4-oxothiazolidines, induced in the presence of Lawesson's reagent by intramolecular non-bonded 1,5-type S⋯O interactions in the 4-oxothiazolidine precursors.

Keywords:

1,2-Dithioles / 1,3-Thiazines / Non-bonded S⋯O interaction / Rearrangement / Thiazolidines

Source:
Tetrahedron, 2007, 63, 9, 1937-1945

Publisher:

Elsevier

Funding / projects:

The Ministry of Science, Technology and Development of the Republic of Serbia, grant no. 1709

Note:

Peer-reviewed version: https://cer.ihtm.bg.ac.rs/handle/123456789/4587
Crystallographic data (CCDC 607823): https://cer.ihtm.bg.ac.rs/handle/123456789/4588
Crystallographic data (CCDC 607824): https://cer.ihtm.bg.ac.rs/handle/123456789/4589

Related info:

Version of
https://cer.ihtm.bg.ac.rs/handle/123456789/4587
Referenced by
https://cer.ihtm.bg.ac.rs/handle/123456789/4588
Referenced by
https://cer.ihtm.bg.ac.rs/handle/123456789/4589

DOI: 10.1016/j.tet.2006.12.075

ISSN: 0040-4020

WoS: 000244406500007

Scopus: 2-s2.0-33846417967

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TY  - JOUR
AU  - Rašović, Aleksandar
AU  - Steel, Peter J.
AU  - Kleinpeter, Erich
AU  - Marković, Rade
PY  - 2007
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4255
AB  - A new synthetic approach to 2,3-dihydro-4H-1,3-thiazine derivatives based upon reductive rearrangement of 1,2-dithiole-3-ylidene thiones has been developed. In turn, the 1,2-dithiole derivatives were prepared by an efficient ring-opening-closing process of 2-alkylidene-4-oxothiazolidines, induced in the presence of Lawesson's reagent by intramolecular non-bonded 1,5-type S⋯O interactions in the 4-oxothiazolidine precursors.
PB  - Elsevier
T2  - Tetrahedron
T1  - Regioselective synthesis of 1,3-thiazines by sequential 4-oxothiazolidine to 1,2-dithiole to 1,3-thiazine transformations: role of intramolecular non-bonded S/O interactions
VL  - 63
IS  - 9
SP  - 1937
EP  - 1945
DO  - 10.1016/j.tet.2006.12.075
ER  -

@article{
author = "Rašović, Aleksandar and Steel, Peter J. and Kleinpeter, Erich and Marković, Rade",
year = "2007",
abstract = "A new synthetic approach to 2,3-dihydro-4H-1,3-thiazine derivatives based upon reductive rearrangement of 1,2-dithiole-3-ylidene thiones has been developed. In turn, the 1,2-dithiole derivatives were prepared by an efficient ring-opening-closing process of 2-alkylidene-4-oxothiazolidines, induced in the presence of Lawesson's reagent by intramolecular non-bonded 1,5-type S⋯O interactions in the 4-oxothiazolidine precursors.",
publisher = "Elsevier",
journal = "Tetrahedron",
title = "Regioselective synthesis of 1,3-thiazines by sequential 4-oxothiazolidine to 1,2-dithiole to 1,3-thiazine transformations: role of intramolecular non-bonded S/O interactions",
volume = "63",
number = "9",
pages = "1937-1945",
doi = "10.1016/j.tet.2006.12.075"
}

Rašović, A., Steel, P. J., Kleinpeter, E.,& Marković, R.. (2007). Regioselective synthesis of 1,3-thiazines by sequential 4-oxothiazolidine to 1,2-dithiole to 1,3-thiazine transformations: role of intramolecular non-bonded S/O interactions. in Tetrahedron
Elsevier., 63(9), 1937-1945.
https://doi.org/10.1016/j.tet.2006.12.075

Rašović A, Steel PJ, Kleinpeter E, Marković R. Regioselective synthesis of 1,3-thiazines by sequential 4-oxothiazolidine to 1,2-dithiole to 1,3-thiazine transformations: role of intramolecular non-bonded S/O interactions. in Tetrahedron. 2007;63(9):1937-1945.
doi:10.1016/j.tet.2006.12.075 .

Rašović, Aleksandar, Steel, Peter J., Kleinpeter, Erich, Marković, Rade, "Regioselective synthesis of 1,3-thiazines by sequential 4-oxothiazolidine to 1,2-dithiole to 1,3-thiazine transformations: role of intramolecular non-bonded S/O interactions" in Tetrahedron, 63, no. 9 (2007):1937-1945,
https://doi.org/10.1016/j.tet.2006.12.075 . .