Thiazine-2-thiones as Masked 1-Azadienes in Cascade Dimerization Reactions

Art Kruithof; Christophe M. L. Vande Velde; Eelco Ruijter; Romano V. A. Orru

doi:10.3390/molecules22040541

Thiazine-2-thiones as Masked 1-Azadienes in Cascade Dimerization Reactions

Art Kruithof, Christophe M. L. Vande Velde, Eelco Ruijter, Romano V. A. Orru

Research output: Contribution to Journal › Article › Academic › peer-review

Abstract

We report the unexpected formation of a 1-Azadiene dimer from 4,6-diphenyl-3,6-dihydro- 2H-1,3-Thiazine-2-Thiones under prolonged microwave irradiation. In this manner, thiazine-2-Thiones act as "masked" 1-Azadiene equivalents, which makes them useful synthetic tools to access complex heterocyclic frameworks. We compare this dimerization with earlier approaches and elaborate on the observed diastereoselectivity.

Original language	English
Article number	541
Journal	Molecules
Volume	22
Issue number	4
DOIs	https://doi.org/10.3390/molecules22040541
Publication status	Published - Apr 2017

Keywords

1-azadienes
aza-Diels-Alder
chemical space
microwave
molecular diversity
multicomponent reaction
tetrahydropyrimidines
thiazine-2-thiones

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10.3390/molecules22040541

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title = "Thiazine-2-thiones as Masked 1-Azadienes in Cascade Dimerization Reactions",

abstract = "We report the unexpected formation of a 1-Azadiene dimer from 4,6-diphenyl-3,6-dihydro- 2H-1,3-Thiazine-2-Thiones under prolonged microwave irradiation. In this manner, thiazine-2-Thiones act as {"}masked{"} 1-Azadiene equivalents, which makes them useful synthetic tools to access complex heterocyclic frameworks. We compare this dimerization with earlier approaches and elaborate on the observed diastereoselectivity.",

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language = "English",

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AU - Kruithof, Art

AU - Velde, Christophe M. L. Vande

AU - Ruijter, Eelco

AU - Orru, Romano V. A.

PY - 2017/4

Y1 - 2017/4

N2 - We report the unexpected formation of a 1-Azadiene dimer from 4,6-diphenyl-3,6-dihydro- 2H-1,3-Thiazine-2-Thiones under prolonged microwave irradiation. In this manner, thiazine-2-Thiones act as "masked" 1-Azadiene equivalents, which makes them useful synthetic tools to access complex heterocyclic frameworks. We compare this dimerization with earlier approaches and elaborate on the observed diastereoselectivity.

AB - We report the unexpected formation of a 1-Azadiene dimer from 4,6-diphenyl-3,6-dihydro- 2H-1,3-Thiazine-2-Thiones under prolonged microwave irradiation. In this manner, thiazine-2-Thiones act as "masked" 1-Azadiene equivalents, which makes them useful synthetic tools to access complex heterocyclic frameworks. We compare this dimerization with earlier approaches and elaborate on the observed diastereoselectivity.

KW - 1-azadienes

KW - aza-Diels-Alder

KW - chemical space

KW - microwave

KW - molecular diversity

KW - multicomponent reaction

KW - tetrahydropyrimidines

KW - thiazine-2-thiones

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U2 - 10.3390/molecules22040541

DO - 10.3390/molecules22040541

M3 - Article

SN - 1420-3049

VL - 22

JO - Molecules

JF - Molecules

IS - 4

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ER -

Thiazine-2-thiones as Masked 1-Azadienes in Cascade Dimerization Reactions

Abstract

Keywords

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CCDC 1415230: Experimental Crystal Structure Determination

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Thiazine-2-thiones as Masked 1-Azadienes in Cascade Dimerization Reactions

Abstract

Keywords

UN SDGs

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Datasets

CCDC 1415230: Experimental Crystal Structure Determination

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