Iodocyclization of S–(homo)propargyl dithiocarbamates: Regiospecific synthesis of 2-imino(iminium)-1, 3-dithiolanes/dithianes/dithiepanes

Farinaz Soleymani; Azim Ziyaei Halimehjani; Farzane Jafari Asar; Gregory R.J. Thatcher

doi:10.1016/j.tetlet.2023.154702

Iodocyclization of S–(homo)propargyl dithiocarbamates: Regiospecific synthesis of 2-imino(iminium)-1, 3-dithiolanes/dithianes/dithiepanes

Farinaz Soleymani
, Azim Ziyaei Halimehjani
, Farzane Jafari Asar
, Gregory R.J. Thatcher

Pharmacology and Toxicology

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

13 Scopus citations

Abstract

An efficient, simple and regiospecific protocol for the synthesis of iodine-containing 2-imino(iminium)1,3- dithiolanes/dithianes/dithiepanes is reported via iodocyclization of corresponding S-(homo)propargyl dihtiocarbamates with molecular iodine. The reactions are regiospecific and only the exo-dig cyclization products were observed in all the cases. In addition, mild reaction conditions, high yields, easy purification, and using inexpensive reagents are the main advantages of this protocol.

Original language	English (US)
Article number	154702
Journal	Tetrahedron Letters
Volume	128
DOIs	https://doi.org/10.1016/j.tetlet.2023.154702
State	Published - Sep 19 2023

Keywords

1,3-dithiolanes
Alkynes
Dithiocarbamates
Exo-dig cyclization
Iodocyclization

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2023.154702

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title = "Iodocyclization of S–(homo)propargyl dithiocarbamates: Regiospecific synthesis of 2-imino(iminium)-1, 3-dithiolanes/dithianes/dithiepanes",

abstract = "An efficient, simple and regiospecific protocol for the synthesis of iodine-containing 2-imino(iminium)1,3- dithiolanes/dithianes/dithiepanes is reported via iodocyclization of corresponding S-(homo)propargyl dihtiocarbamates with molecular iodine. The reactions are regiospecific and only the exo-dig cyclization products were observed in all the cases. In addition, mild reaction conditions, high yields, easy purification, and using inexpensive reagents are the main advantages of this protocol.",

keywords = "1,3-dithiolanes, Alkynes, Dithiocarbamates, Exo-dig cyclization, Iodocyclization",

author = "Farinaz Soleymani and \{Ziyaei Halimehjani\}, Azim and Asar, \{Farzane Jafari\} and Thatcher, \{Gregory R.J.\}",

note = "Publisher Copyright: {\textcopyright} 2023 Elsevier Ltd",

year = "2023",

month = sep,

day = "19",

doi = "10.1016/j.tetlet.2023.154702",

language = "English (US)",

volume = "128",

journal = "Tetrahedron Letters",

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T1 - Iodocyclization of S–(homo)propargyl dithiocarbamates

T2 - Regiospecific synthesis of 2-imino(iminium)-1, 3-dithiolanes/dithianes/dithiepanes

AU - Soleymani, Farinaz

AU - Ziyaei Halimehjani, Azim

AU - Asar, Farzane Jafari

AU - Thatcher, Gregory R.J.

PY - 2023/9/19

Y1 - 2023/9/19

N2 - An efficient, simple and regiospecific protocol for the synthesis of iodine-containing 2-imino(iminium)1,3- dithiolanes/dithianes/dithiepanes is reported via iodocyclization of corresponding S-(homo)propargyl dihtiocarbamates with molecular iodine. The reactions are regiospecific and only the exo-dig cyclization products were observed in all the cases. In addition, mild reaction conditions, high yields, easy purification, and using inexpensive reagents are the main advantages of this protocol.

AB - An efficient, simple and regiospecific protocol for the synthesis of iodine-containing 2-imino(iminium)1,3- dithiolanes/dithianes/dithiepanes is reported via iodocyclization of corresponding S-(homo)propargyl dihtiocarbamates with molecular iodine. The reactions are regiospecific and only the exo-dig cyclization products were observed in all the cases. In addition, mild reaction conditions, high yields, easy purification, and using inexpensive reagents are the main advantages of this protocol.

KW - 1,3-dithiolanes

KW - Alkynes

KW - Dithiocarbamates

KW - Exo-dig cyclization

KW - Iodocyclization

UR - https://www.scopus.com/pages/publications/85168279227

UR - https://www.scopus.com/pages/publications/85168279227#tab=citedBy

U2 - 10.1016/j.tetlet.2023.154702

DO - 10.1016/j.tetlet.2023.154702

M3 - Article

AN - SCOPUS:85168279227

SN - 0040-4039

VL - 128

JO - Tetrahedron Letters

JF - Tetrahedron Letters

M1 - 154702

ER -

Iodocyclization of S–(homo)propargyl dithiocarbamates: Regiospecific synthesis of 2-imino(iminium)-1, 3-dithiolanes/dithianes/dithiepanes

Abstract

Keywords

ASJC Scopus subject areas

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