Multicomponent synthesis of 3,6-dihydro-2H-1,3-thiazine-2-thiones

Art Kruithof; Marten L Ploeger; Elwin Janssen; Madeleine Helliwell; Frans J J de Kanter; Eelco Ruijter; Romano V A Orru

doi:10.3390/molecules17021675

Multicomponent synthesis of 3,6-dihydro-2H-1,3-thiazine-2-thiones

Art Kruithof, Marten L Ploeger, Elwin Janssen, Madeleine Helliwell, Frans J J de Kanter, Eelco Ruijter, Romano V A Orru

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Abstract

Non-fused 3,6-dihydro-2H-1,3-thiazine-2-thiones constitute a so far rather unexplored class of compounds, with the latest report dating back more than two decades. Thiazine-2-thiones contain an endocyclic dithiocarbamate group, which is often found in pesticides, in substrates for radical chemistry and in synthetic intermediates towards thioureas and amidines. We now report the multicomponent reaction (MCR) of in situ-generated 1-azadienes with carbon disulfide. With this reaction, a one-step protocol towards the potentially interesting 3,6-dihydro-2H-1,3-thiazine-2-thiones was established and a small library was synthesized.

Original language	English
Pages (from-to)	1675-1685
Number of pages	11
Journal	Molecules
Volume	17
Issue number	2
DOIs	https://doi.org/10.3390/molecules17021675
Publication status	Published - 8 Feb 2012

Keywords

Magnetic Resonance Spectroscopy
Mass Spectrometry
Thiazines/chemical synthesis
Thiones/chemical synthesis

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This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.3390/molecules17021675

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CCDC 865856: Experimental Crystal Structure Determination
Kruithof, A. (Contributor), Ploeger, M. L. (Contributor), Janssen, E. (Contributor), Helliwell, M. (Contributor), De Kanter, F. J. J. (Contributor), Ruijter, E. (Contributor) & Orru, R. V. A. (Contributor), Unknown Publisher, 1 Feb 2012
DOI: 10.5517/ccy1zvs, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccy1zvs&sid=DataCite
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title = "Multicomponent synthesis of 3,6-dihydro-2H-1,3-thiazine-2-thiones",

abstract = "Non-fused 3,6-dihydro-2H-1,3-thiazine-2-thiones constitute a so far rather unexplored class of compounds, with the latest report dating back more than two decades. Thiazine-2-thiones contain an endocyclic dithiocarbamate group, which is often found in pesticides, in substrates for radical chemistry and in synthetic intermediates towards thioureas and amidines. We now report the multicomponent reaction (MCR) of in situ-generated 1-azadienes with carbon disulfide. With this reaction, a one-step protocol towards the potentially interesting 3,6-dihydro-2H-1,3-thiazine-2-thiones was established and a small library was synthesized.",

keywords = "Magnetic Resonance Spectroscopy, Mass Spectrometry, Thiazines/chemical synthesis, Thiones/chemical synthesis",

author = "Art Kruithof and Ploeger, {Marten L} and Elwin Janssen and Madeleine Helliwell and {de Kanter}, {Frans J J} and Eelco Ruijter and Orru, {Romano V A}",

year = "2012",

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doi = "10.3390/molecules17021675",

language = "English",

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pages = "1675--1685",

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T1 - Multicomponent synthesis of 3,6-dihydro-2H-1,3-thiazine-2-thiones

AU - Kruithof, Art

AU - Ploeger, Marten L

AU - Janssen, Elwin

AU - Helliwell, Madeleine

AU - de Kanter, Frans J J

AU - Ruijter, Eelco

AU - Orru, Romano V A

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N2 - Non-fused 3,6-dihydro-2H-1,3-thiazine-2-thiones constitute a so far rather unexplored class of compounds, with the latest report dating back more than two decades. Thiazine-2-thiones contain an endocyclic dithiocarbamate group, which is often found in pesticides, in substrates for radical chemistry and in synthetic intermediates towards thioureas and amidines. We now report the multicomponent reaction (MCR) of in situ-generated 1-azadienes with carbon disulfide. With this reaction, a one-step protocol towards the potentially interesting 3,6-dihydro-2H-1,3-thiazine-2-thiones was established and a small library was synthesized.

AB - Non-fused 3,6-dihydro-2H-1,3-thiazine-2-thiones constitute a so far rather unexplored class of compounds, with the latest report dating back more than two decades. Thiazine-2-thiones contain an endocyclic dithiocarbamate group, which is often found in pesticides, in substrates for radical chemistry and in synthetic intermediates towards thioureas and amidines. We now report the multicomponent reaction (MCR) of in situ-generated 1-azadienes with carbon disulfide. With this reaction, a one-step protocol towards the potentially interesting 3,6-dihydro-2H-1,3-thiazine-2-thiones was established and a small library was synthesized.

KW - Magnetic Resonance Spectroscopy

KW - Mass Spectrometry

KW - Thiazines/chemical synthesis

KW - Thiones/chemical synthesis

U2 - 10.3390/molecules17021675

DO - 10.3390/molecules17021675

M3 - Article

C2 - 22318323

SN - 1420-3049

VL - 17

SP - 1675

EP - 1685

JO - Molecules

JF - Molecules

IS - 2

ER -

Multicomponent synthesis of 3,6-dihydro-2H-1,3-thiazine-2-thiones

Abstract

Keywords

UN SDGs

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Datasets

CCDC 865856: Experimental Crystal Structure Determination

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