581
Chemistry of Heterocyclic Compounds 2018, 54(6), 581–583
1,4-Dithiane-2,5-diol in the synthesis of thiophenes (microreview)
Seyed Sajad Sajadikhah
1
*, Malek Taher Maghsoodlou
2
1
Department of Chemistry, Payame Noor University,
P. O. Box 19395-3697, Tehran, Iran; е-mail: sssajadi@pnu.ac.ir
2
Department of Chemistry, Faculty of Science, University of Sistan and Baluchestan,
P. O. Box 98135-674, Zahedan, Iran; e-mail: mt_maghsoodlou@chem.usb.ac.ir
Submitted April 7, 2018
Accepted May 21, 2018
Malek Taher Maghsoodlou was born in 1955 in
Gorgan, Iran. He got his BSc in Pure Chemistry
from the Razi University of Kermanshah, MSc in
Organic Chemistry from the Tabriz University and
PhD in Organic Chemistry from the Tarbiat Modares
University. Currently Prof. M. T. Maghsoodlou is
a faculty member of the Department of Chemistry
at the University of Sistan and Baluchestan,
Zahedan, Iran. His research interests include
organic synthesis, heterocyclic chemistry, organo-
phosphorus compounds, and dynamic NMR.
Seyed Sajad Sajadikhah was born in 1982 in
Mamasani, Iran. He obtained his BSc in Pure
Chemistry from the University of Isfahan, MSc
and PhD in Organic Chemistry under supervision
of Prof. M. T. Maghsoodlou from the University
of Sistan and Baluchestan, Zahedan. Currently he
is a faculty member of the Department of
Chemistry at the Payame Noor University, Iran.
His research focuses on the heterocyclic
chemistry, catalysts, and organic synthesis.
Additionally, these heterocycles were reported as key
building blocks of compounds with photochromic pro-
perties.
3
Therefore, numerous efficient routes have been
introduced for the synthesis of thiophene derivatives.
Among these methods, the use of 1,4-dithiane-2,5-diol as
sulfanylacetaldehyde synthon has received extensive
attention.
Introduction
Thiophene and its derivatives have attracted attention due
to their wide pharmaceutical and biological activities such
as antioxidant, antimicrobial, antihypertensive, antiosteo-
porosis, anti-inflammatory, antipsychotic, and anti-
convulsant.
1
They can also act as HIV inhibitors,
glucosidase inhibitors, potential JNK2 and JNK3 kinase
inhibitors, adenosine agonists, and mimics of penicillins.
2
This microreview provides insight on the selected methods of thiophene synthesis starting from 1,4-dithiane-2,5-diol
including K
2
CO
3
- and DABCO-catalyzed reactions, cyclopropane-based reactions, heterocyclization of alkynones,
tandem Michael – intramolecular Henry reaction, Gewald reaction and thiophene ring construction as a part of fused
and polycyclic structures. Microreview covers literature from 2010 to 2017.
K
2
CO
3
-catalyzed reactions
The reaction between 1,4-dithiane-2,5-diol (1) and α-azido
vinyl ketones 2 catalyzed by K
2
CO
3
in DMF gave 3,5-di-
substituted 4-aminothiophene-2-carbaldehydes 3 in mode-
rate to high yields.
4
Kumar et al. described the synthesis of 3-nitrothiophen-
2-amines 5 via the reaction of 1,4-dithiane-2,5-diol (1) and
1-(methylsulfanyl)-2-nitroethenamines 4 in the presence of
K
2
CO
3
in refluxing EtOH.
5
Kumara et al. reported another K
2
CO
3
-catalyzed reaction of
compound 1 and α-oxoketene dithioacetals 6 in boiling
EtOH for the preparation of 2-(methylsulfanyl)thiophenes 7
in moderate to good yields.
6
Published in Khimiya Geterotsiklicheskikh Soedinenii,
2018, 54(6), 581–583
0009-3122/18/54(6)-0581©2018 Springer Science+Business Media, LLC
Here and further the corresponding author is marked with*.
DOI 10.1007/s10593-018-2309-8