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^*

^*Bu çalışma için yazışmadan sorumlu yazar

Kimya Bölümü

Istanbul Technical University

Araştırma çıktısı: Dergi yayını › Makale › Hakem

6 Atıf (Scopus)

Özet

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.

Orijinal dil	İngilizce
Sayfa (başlangıç-bitiş)	4028-4032
Sayfa sayısı	5
Dergi	Organic Letters
Hacim	25
Basın numarası	22
DOI'lar	https://doi.org/10.1021/acs.orglett.3c01118
Yayın durumu	Yayınlandı - 9 Haz 2023

Bibliyografik not

Publisher Copyright:
© 2023 American Chemical Society.

Finansman

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.

Finansörler	Finansör numarası
Türkiye Bilimsel ve Teknolojik Araştırma Kurumu	KBAG-119Z533

Belgeye Erişim

10.1021/acs.orglett.3c01118

Diğer Dosyalar ve Linkler

Link to publication in Scopus

Alıntı Yap

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

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.",

author = "Mert Dinc and Eda Ismailoglu and Zeynep Mert and Kerem Kaya and Melda Tayanc and Baris Yucel",

note = "Publisher Copyright: {\textcopyright} 2023 American Chemical Society.",

year = "2023",

month = jun,

day = "9",

doi = "10.1021/acs.orglett.3c01118",

language = "English",

volume = "25",

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journal = "Organic Letters",

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T1 - Base-Mediated Rearrangement of α-Dithioacetyl Propargylamines via Expansion of Dithioacetyl Ring

T2 - Synthesis of Medium-Sized S,S-Heterocycles

AU - Dinc, Mert

AU - Ismailoglu, Eda

AU - Mert, Zeynep

AU - Kaya, Kerem

AU - Tayanc, Melda

AU - Yucel, Baris

PY - 2023/6/9

Y1 - 2023/6/9

N2 - 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.

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.

UR - https://www.scopus.com/pages/publications/85162814948

U2 - 10.1021/acs.orglett.3c01118

DO - 10.1021/acs.orglett.3c01118

M3 - Article

C2 - 37232086

AN - SCOPUS:85162814948

SN - 1523-7060

VL - 25

SP - 4028

EP - 4032

JO - Organic Letters

JF - Organic Letters

IS - 22

ER -

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

Özet

Bibliyografik not

Finansman

Belgeye Erişim

Diğer Dosyalar ve Linkler

Parmak izi

Alıntı Yap