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

Mert Dinc; Eda Ismailoglu; Zeynep Mert; Kerem Kaya; Melda Tayanc; Baris Yucel

doi:10.1021/acs.orglett.3c01118

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

Mert Dinc, Eda Ismailoglu, Zeynep Mert, Kerem Kaya, Melda Tayanc, Baris Yucel^*

^*Corresponding author for this work

Department of Chemistry

Istanbul Technical University

Research output: Contribution to journal › Article › peer-review

2 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	4028-4032
Number of pages	5
Journal	Organic Letters
Volume	25
Issue number	22
DOIs	https://doi.org/10.1021/acs.orglett.3c01118
Publication status	Published - 9 Jun 2023

Bibliographical note

Publisher Copyright:
© 2023 American Chemical Society.

Funding

This study was funded by The Scientific and Technological Research Council of Turkey (TUBITAK) (project no. KBAG-119Z533). We would like to thank TUBITAK for its support. The authors thank the Research Board of Istanbul Technical University (TGA-2021-43104 and TYL-2022-44156) for its support and METU Central Laboratory for HRMS measurements.

Funders	Funder number
Türkiye Bilimsel ve Teknolojik Araştırma Kurumu	KBAG-119Z533

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abstract = "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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AU - Dinc, Mert

AU - Ismailoglu, Eda

AU - Mert, Zeynep

AU - Kaya, Kerem

AU - Tayanc, Melda

AU - Yucel, Baris

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

Abstract

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