Base-Mediated Rearrangement of α-Dithioacetyl Propargylamines via Expansion of Dithioacetyl Ring: Synthesis of Medium-Sized S,S-Heterocycles

[Image: see text] Base-mediated rearrangement of 1,3-dithianyl-substituted propargylamines in DMF via expansion of the dithiane ring has been reported. The rearrangement provided 9-membered amino-functionalized sulfur-containing heterocycles (dithionine derivatives) in good yields under mild conditi...

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Autores principales: Dinc, Mert, Ismailoglu, Eda, Mert, Zeynep, Kaya, Kerem, Tayanc, Melda, Yucel, Baris
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10262264/
https://www.ncbi.nlm.nih.gov/pubmed/37232086
http://dx.doi.org/10.1021/acs.orglett.3c01118
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author Dinc, Mert
Ismailoglu, Eda
Mert, Zeynep
Kaya, Kerem
Tayanc, Melda
Yucel, Baris
author_facet Dinc, Mert
Ismailoglu, Eda
Mert, Zeynep
Kaya, Kerem
Tayanc, Melda
Yucel, Baris
author_sort Dinc, Mert
collection PubMed
description [Image: see text] Base-mediated rearrangement of 1,3-dithianyl-substituted propargylamines in DMF via expansion of the dithiane ring has been reported. The rearrangement provided 9-membered amino-functionalized sulfur-containing heterocycles (dithionine derivatives) in good yields under mild conditions. Propargylamines bearing 5-membered 1,3-dithiolane and 7-membered 1,3-dithiepane rings rearranged in a similar manner yielding 8- and 10-membered S,S-heterocycles, respectively.
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spelling pubmed-102622642023-06-15 Base-Mediated Rearrangement of α-Dithioacetyl Propargylamines via Expansion of Dithioacetyl Ring: Synthesis of Medium-Sized S,S-Heterocycles Dinc, Mert Ismailoglu, Eda Mert, Zeynep Kaya, Kerem Tayanc, Melda Yucel, Baris Org Lett [Image: see text] Base-mediated rearrangement of 1,3-dithianyl-substituted propargylamines in DMF via expansion of the dithiane ring has been reported. The rearrangement provided 9-membered amino-functionalized sulfur-containing heterocycles (dithionine derivatives) in good yields under mild conditions. Propargylamines bearing 5-membered 1,3-dithiolane and 7-membered 1,3-dithiepane rings rearranged in a similar manner yielding 8- and 10-membered S,S-heterocycles, respectively. American Chemical Society 2023-05-26 /pmc/articles/PMC10262264/ /pubmed/37232086 http://dx.doi.org/10.1021/acs.orglett.3c01118 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Dinc, Mert
Ismailoglu, Eda
Mert, Zeynep
Kaya, Kerem
Tayanc, Melda
Yucel, Baris
Base-Mediated Rearrangement of α-Dithioacetyl Propargylamines via Expansion of Dithioacetyl Ring: Synthesis of Medium-Sized S,S-Heterocycles
title Base-Mediated Rearrangement of α-Dithioacetyl Propargylamines via Expansion of Dithioacetyl Ring: Synthesis of Medium-Sized S,S-Heterocycles
title_full Base-Mediated Rearrangement of α-Dithioacetyl Propargylamines via Expansion of Dithioacetyl Ring: Synthesis of Medium-Sized S,S-Heterocycles
title_fullStr Base-Mediated Rearrangement of α-Dithioacetyl Propargylamines via Expansion of Dithioacetyl Ring: Synthesis of Medium-Sized S,S-Heterocycles
title_full_unstemmed Base-Mediated Rearrangement of α-Dithioacetyl Propargylamines via Expansion of Dithioacetyl Ring: Synthesis of Medium-Sized S,S-Heterocycles
title_short Base-Mediated Rearrangement of α-Dithioacetyl Propargylamines via Expansion of Dithioacetyl Ring: Synthesis of Medium-Sized S,S-Heterocycles
title_sort base-mediated rearrangement of α-dithioacetyl propargylamines via expansion of dithioacetyl ring: synthesis of medium-sized s,s-heterocycles
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10262264/
https://www.ncbi.nlm.nih.gov/pubmed/37232086
http://dx.doi.org/10.1021/acs.orglett.3c01118
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