Synthesis of 3-Amino-4-iodothiophenes through Iodocyclization of 1-(1,3-Dithian-2-yl)propargylamines

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

doi:10.1002/ejoc.202100483

Synthesis of 3-Amino-4-iodothiophenes through Iodocyclization of 1-(1,3-Dithian-2-yl)propargylamines

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

^*Bu çalışma için yazışmadan sorumlu yazar

Kimya Bölümü

Istanbul Technical University

Araştırma sonucu: Dergiye katkı › Makale › bilirkişi

3 Atıf (Scopus)

Özet

1-(1,3-Dithian-2-yl)propargylamines undergo iodo-cylization regioselectively to afford tetrasubstituted 3-amino-4-iodothiophenes in 30–87 % yields by iodide induced cleavage of dithiane ring in a bicyclic sulfonium intermediate. A mechanism for this unprecedented transformation was proposed and tentatively supported by the isolation of an intermediate structure. 1-(1,3-Dithian-2-yl)propargylamines were prepared in 30–94 % yields by Au-catalyzed one-pot, three-component reaction of 1,3-dithiane-2-carbaldehydes, amines, and alkynes so called A³-coupling reaction.

Orijinal dil	İngilizce
Sayfa (başlangıç-bitiş)	4107-4124
Sayfa sayısı	18
Dergi	European Journal of Organic Chemistry
Hacim	2021
Basın numarası	29
DOI'lar	https://doi.org/10.1002/ejoc.202100483
Yayın durumu	Yayınlandı - 6 Ağu 2021

Bibliyografik not

Publisher Copyright:
© 2021 Wiley-VCH GmbH

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. Authors thank to Research Board of Istanbul Technical University and METU Central Laboratory for HRMS measurements and Giresun University Central Laboratory for X‐ray single crystal diffraction measurements. Authors also thank to Dr. Armagan Atsay for NMR measurements. 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. Authors thank to Research Board of Istanbul Technical University and METU Central Laboratory for HRMS measurements and Giresun University Central Laboratory for X-ray single crystal diffraction measurements. Authors also thank to Dr. Armagan Atsay for NMR measurements.

Finansörler	Finansör numarası
METU
TUBITAK	KBAG‐119Z533
Türkiye Bilimsel ve Teknolojik Araştirma Kurumu
Istanbul Teknik Üniversitesi

Belgeye Erişim

10.1002/ejoc.202100483

Diğer Dosyalar ve Linkler

Link to publication in Scopus

Alıntı Yap

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title = "Synthesis of 3-Amino-4-iodothiophenes through Iodocyclization of 1-(1,3-Dithian-2-yl)propargylamines",

abstract = "1-(1,3-Dithian-2-yl)propargylamines undergo iodo-cylization regioselectively to afford tetrasubstituted 3-amino-4-iodothiophenes in 30–87 % yields by iodide induced cleavage of dithiane ring in a bicyclic sulfonium intermediate. A mechanism for this unprecedented transformation was proposed and tentatively supported by the isolation of an intermediate structure. 1-(1,3-Dithian-2-yl)propargylamines were prepared in 30–94 % yields by Au-catalyzed one-pot, three-component reaction of 1,3-dithiane-2-carbaldehydes, amines, and alkynes so called A3-coupling reaction.",

keywords = "1,3-Dithiane, A-coupling, Iodocyclization, Iodothiophene, Sulfonium ion",

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

note = "Publisher Copyright: {\textcopyright} 2021 Wiley-VCH GmbH",

year = "2021",

month = aug,

day = "6",

doi = "10.1002/ejoc.202100483",

language = "English",

volume = "2021",

pages = "4107--4124",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley-VCH Verlag",

number = "29",

}

TY - JOUR

T1 - Synthesis of 3-Amino-4-iodothiophenes through Iodocyclization of 1-(1,3-Dithian-2-yl)propargylamines

AU - Ismailoglu, Eda

AU - Mert, Zeynep

AU - Dinc, Mert

AU - Kaya, Kerem

AU - Yucel, Baris

PY - 2021/8/6

Y1 - 2021/8/6

N2 - 1-(1,3-Dithian-2-yl)propargylamines undergo iodo-cylization regioselectively to afford tetrasubstituted 3-amino-4-iodothiophenes in 30–87 % yields by iodide induced cleavage of dithiane ring in a bicyclic sulfonium intermediate. A mechanism for this unprecedented transformation was proposed and tentatively supported by the isolation of an intermediate structure. 1-(1,3-Dithian-2-yl)propargylamines were prepared in 30–94 % yields by Au-catalyzed one-pot, three-component reaction of 1,3-dithiane-2-carbaldehydes, amines, and alkynes so called A3-coupling reaction.

AB - 1-(1,3-Dithian-2-yl)propargylamines undergo iodo-cylization regioselectively to afford tetrasubstituted 3-amino-4-iodothiophenes in 30–87 % yields by iodide induced cleavage of dithiane ring in a bicyclic sulfonium intermediate. A mechanism for this unprecedented transformation was proposed and tentatively supported by the isolation of an intermediate structure. 1-(1,3-Dithian-2-yl)propargylamines were prepared in 30–94 % yields by Au-catalyzed one-pot, three-component reaction of 1,3-dithiane-2-carbaldehydes, amines, and alkynes so called A3-coupling reaction.

KW - 1,3-Dithiane

KW - A-coupling

KW - Iodocyclization

KW - Iodothiophene

KW - Sulfonium ion

UR - http://www.scopus.com/inward/record.url?scp=85107838184&partnerID=8YFLogxK

U2 - 10.1002/ejoc.202100483

DO - 10.1002/ejoc.202100483

M3 - Article

AN - SCOPUS:85107838184

SN - 1434-193X

VL - 2021

SP - 4107

EP - 4124

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 29

ER -

Synthesis of 3-Amino-4-iodothiophenes through Iodocyclization of 1-(1,3-Dithian-2-yl)propargylamines

Özet

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Finansman

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