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Topic:Thiophene
Provider:YasaminJahani
Lesson teacher: Dr.Khalifeh
Date: Monday
INTHE NAMEOF GOD
Thiophene
Synthesis, properties of thiophene
Introduction
Molecular mass: 84.14 g / mol
Density: 1.051 g / ml liquid
Appearance: colorless liquid
Melting point: _38 ° C
boiling point: 84.4 °C (at 760 mmHg)
soluble in most organic solventslike
alcohol and ether
 insolublein water
ROUTES FOR
THIOPHENE
NUCLEUS
FORMATION
Synthetic approaches to the construction of
thiophene and substituted thiophene have been
efficiently developed. Thiophene ring can be
constructed from non-heterocyclic precursors by
two reaction pathways:
1. Construction of thiophene ring
fromappropriately substituted open chain
precursors:
This method involves the introduction of sulphur
into a starting material containing the complete
carbon skeleton.
2. The functionalization at the positions α and β
to the sulphur atom of the preconstructed
thiophene nucleus.
A. Paal- Knorr Thiophene Synthesis
B. FiesselmannThiopheneSynthesis
C. Gewald AminothiopheneSynthesis
D. The Hinsberg Synthesis
MAJOR
SYNTHETIC
PROCEDURES
MAJOR
SYNTHETIC
PROCEDURES
A. Paal- Knorr Thiophene Synthesis:
This reaction is also known as Paal Thiophene Synthesis.
1, 4
- Dicarbonyl compounds can be reacted with a source
of sulfur to give thiophene.
Sort of S:
Paal- Knorr
Thiophene
Synthesis
Paal- Knorr
Thiophene
Synthesis
Based on the above observations, it was proposed that the mechanism
involves initial formation of thione (X = O or S), which is followed by
tautomerization and cyclization. Aromaticity drives the facile
elimination of either H2O or H2S resulting in the thiophene product.
E. Campaigne,W. O. Foye;J. Org.Chem; 1952;17; 1405
Fiesselmann
Thiophene
Synthesis
B. FiesselmannThiopheneSynthesis:
Condensation reaction of thioglycolic acid with α, β- acetylenic
esters, which upon treatment with base result in the formation of 3-
hydroxyl- 2- thiophenecarboxylic acid[11].
FiesselmannThiophene Synthesis is an extension ofWoodward
condensation of thioglycolic acid[12] and α, β- unsaturated ester in
the presence of base to produce 2-carbomethoxy-
ketotetrahydrothiophene.
Fiesselmannthiophenesynthesis; Name Reactions; 2006, 230
Fiesselmann
Thiophene
Synthesis
Gewald
Aminothiophe
ne Synthesis
C. Gewald AminothiopheneSynthesis :
This method was reported by Gewald in 1966[13].
Gewald synthesis is the usual route to 2-
aminothiophenes. It consists of the base-catalyzed
condensation of a ketone having an a CH2group with a
β-ketonitrile to form an olefin, followed by cyclisation
with elemental sulfur.
K. Gewald, E. Schinke,H. Bottcher; Chem. Ber.; 1966; 99;94.
Gewald
Aminothiophe
ne Synthesis
The Hinsberg
Synthesis
D. The Hinsberg Synthesis:
Two consecutive aldol condensations between a 1, 2-dicarbony1
compound and diethy1 thiodiacetates gives thiophene. The
immediate product is an ester-acid produced[19] by a Stobbe-type
mechanism but the reactions are often worked up via hydrolysis to
afford an isolated diacid:
H. Wynberg, H. J. Kooreman;J. Ame. Chem. Soc.; 1965;87; 1739
GENERAL
SYNTHETIC
PROCEDURE
S
A. From thiocarbonyl compounds :
2-Keto-thiols added to alkenyl phosphonium ions
followed by ring closure via Witting reaction gives 2, 5-
dihydrothiophenes which can be dehydrogenated[20].
J. M. Mclntosh,H. Khalil;Can. J. Chem.; 1975; 53; 209
B. Using carbon disulfid:
2-alkylthiophenes[21] can be synthesized by the addition of a
carbanion to carbon disulfide with a subsequent S-alkylation.
GENERAL
SYNTHETIC
PROCEDURE
S
D. Prim,G. Kirsh;Synth. Comm.; 1995;25; 2449
C. From thio-nitroacetamides:
The S-alkylation of thio-nitroacetamides with 2-bromoketones
produces 2-amino-3-nitrothiophenes[22].
GENERAL
SYNTHETIC
PROCEDURE
S
D. Prim,G. Kirsh;Synth. Comm.; 1995;25; 2449
D. From thiazoles:
When thiazoles are heated strongly with an alkyne, generates 2, 5-
unsubstituted thiophenes.
Though the conditions are vigorous, excellent yield can be obtained
GENERAL
SYNTHETIC
PROCEDURE
S
W.You, X.Yan, Q. Liao,C. Xi;Org. Lett.; 2010; 12; 3930
A.Thiophene can be synthesized on industrial scale by the high
temperature reaction between n-
butane and Sulfur.
SYNTHESIS
ON
INDUSTRIAL
SCALE
B.Thiophene can be synthesized by passing a
mixtureacetylene and hydrogen sulfide through a tube
containing alumina at 400°C.This method is
commercially used.
W.You, X.Yan, Q. Liao,C. Xi;Org. Lett.; 2010; 12; 3930
C.Thiophene may also be prepared by heating sodium succinate
with phosphorous trisulphide.
SYNTHESIS
ON
INDUSTRIAL
SCALE
W.You, X.Yan, Q. Liao,C. Xi;Org. Lett.; 2010; 12; 3930
MISCELLANE
OUS
SYNTHETIC
PROCEDURES
Various other methods have been reported for synthesizing
substituted thiophene. Some of them
are as follows:
i)Copper-catalyzed tandem S-alkenylation of potassium sulfide with
1, 4-diiodo-1, 3-dienes
enables an efficient synthetic approach to variously substituted
thiophenes[
 ii)An efficient one-step method for the synthesis of highly
substituted thiophenes from
 thiomorpholides and α-haloketones has been developed[24]
MISCELLANE
OUS
SYNTHETIC
PROCEDURES
 gold-catalyzed carbothiolation provided an atom-economic way
of synthesizing sulfurcontaining heterocycles such as 2,3-
disubstituted benzothiophenes[26].
MISCELLANE
OUS
SYNTHETIC
PROCEDURES
W.You, X.Yan, Q. Liao,C. Xi;Org. Lett.; 2010; 12; 3930
CHEMICAL
BEHAVIOUR
OF
THIOPHENE
a. Reactions with oxidizing reagents
The thiophene ring system is relatively stable to oxidants and side-
chains can be oxidized to
carboxylic acid groups.
b. Reactions with nucleophilic reagents
Nucleophilic displacements proceed atleast hundred times faster
than for benzenoid counterparts.
F. Freeman, M.Y. Lee, H. Lue, X. Wang, E. Rodriguez;J. Org.
Chem.; 1994; 50; 3695
c. Reactions with electrophilic reagents
1.Acylation
2.Sulfonation
3.Nitration
4.Halogenation
5.Condsation with Aldehydes and ketone.
CHEMICAL
BEHAVIOUR
OF
THIOPHENE
Acylation:
CHEMICAL
BEHAVIOUR
OF
THIOPHENE
Sulfonation:
Nitration:
CHEMICAL
BEHAVIOUR
OF
THIOPHENE
Halogenation:
CHEMICAL
BEHAVIOUR
OF
THIOPHENE
Condensation with Aldehydes and ketones:
CHEMICAL
BEHAVIOUR
OF
THIOPHENE
G. Marino;Tetra.; 1965;21; 843.
Thelatest
syntheses of
thiophene
S. Pathania,R. K. Narang, R. K. Rawal Eur. J. Med.Chem. 2019, 180, 486-508.
Eur. J. Org.Chem. 36 (2014), 8167-8181, doi:10.1002/ejoc.201403100
Thelatest
syntheses of
thiophene
This journal is ©The Royal Society ofChemistry 2020
Thelatest
syntheses of
thiophene
C. Zhao, K. Nagura, M. i.Takeuchi and K. Sugiyasu, Polym.J., 2017, 49, 133–139.
Thelatest
syntheses of
thiophene
Thelatest
syntheses of
thiophene
C. Horn, D. Pospiech,J.Zessin,S. Stein, D. Jehnichen,
H. Komber, M. G¨obel, B. Voit andA. Kiriy, Phys.Status
SolidiA, 2019, 216, 1800747–1800753.
C. H.Tsai, A. Fortney,Y. Qiu, R. R. Gil, D.Yaron,
T. Kowalewski and K. J.T. Noonan, J. Am. Chem. Soc.,
2016, 138, 6798–6804.
Thelatest
syntheses of
thiophene
AdiwishWM,YaacobWA, Adan D, NazlinaI (2012) Synthesis
and antibacterialactivityof thiophenes. Int J Adv Sci Eng Inf
Tech 2(4):27–30
Thelatest
syntheses of
thiophene
Gunda SR, LingalaS,AllenkiV(2017) Synthesisand anticanceractivityof some
novel 3-[(2-substituted-6,7,8,9-tetrahydro-5Hcyclohepta[b]thieno[2,3-d]pyrimidin-
4-yl)amino]propan-1-olderivatives.Eur J Pharm Med Res 4(6):481–484
Thelatest
syntheses of
thiophene
. Mohareb RM, AbdallahAE, HelalMH,ShaloofSM (2016) Synthesisand structure
elucidationof some novel thiophene and benzothiophenederivativesas cytotoxicagents.
Acta Pharm 66:53–68.
Thelatest
syntheses of
thiophene
BIOLOGICAL
ACTIVITYAND
SOMEASPECTS
OF PRACTICAL
USEOF
THIOPHENE
In medicinal chemistry, thiophene derivatives have been very well known for their
therapeutic applications. Many thiophene derivatives have been developed as
chemotherapeutic agents and are widely used.
THX FORYOUR ATTENTION

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Thiophen Mechanism khhjjjjjjjhhhhhhhhhhh

  • 3. Introduction Molecular mass: 84.14 g / mol Density: 1.051 g / ml liquid Appearance: colorless liquid Melting point: _38 ° C boiling point: 84.4 °C (at 760 mmHg) soluble in most organic solventslike alcohol and ether  insolublein water
  • 4. ROUTES FOR THIOPHENE NUCLEUS FORMATION Synthetic approaches to the construction of thiophene and substituted thiophene have been efficiently developed. Thiophene ring can be constructed from non-heterocyclic precursors by two reaction pathways: 1. Construction of thiophene ring fromappropriately substituted open chain precursors: This method involves the introduction of sulphur into a starting material containing the complete carbon skeleton. 2. The functionalization at the positions α and β to the sulphur atom of the preconstructed thiophene nucleus.
  • 5. A. Paal- Knorr Thiophene Synthesis B. FiesselmannThiopheneSynthesis C. Gewald AminothiopheneSynthesis D. The Hinsberg Synthesis MAJOR SYNTHETIC PROCEDURES
  • 6. MAJOR SYNTHETIC PROCEDURES A. Paal- Knorr Thiophene Synthesis: This reaction is also known as Paal Thiophene Synthesis. 1, 4 - Dicarbonyl compounds can be reacted with a source of sulfur to give thiophene. Sort of S:
  • 8. Paal- Knorr Thiophene Synthesis Based on the above observations, it was proposed that the mechanism involves initial formation of thione (X = O or S), which is followed by tautomerization and cyclization. Aromaticity drives the facile elimination of either H2O or H2S resulting in the thiophene product. E. Campaigne,W. O. Foye;J. Org.Chem; 1952;17; 1405
  • 9. Fiesselmann Thiophene Synthesis B. FiesselmannThiopheneSynthesis: Condensation reaction of thioglycolic acid with α, β- acetylenic esters, which upon treatment with base result in the formation of 3- hydroxyl- 2- thiophenecarboxylic acid[11]. FiesselmannThiophene Synthesis is an extension ofWoodward condensation of thioglycolic acid[12] and α, β- unsaturated ester in the presence of base to produce 2-carbomethoxy- ketotetrahydrothiophene. Fiesselmannthiophenesynthesis; Name Reactions; 2006, 230
  • 11. Gewald Aminothiophe ne Synthesis C. Gewald AminothiopheneSynthesis : This method was reported by Gewald in 1966[13]. Gewald synthesis is the usual route to 2- aminothiophenes. It consists of the base-catalyzed condensation of a ketone having an a CH2group with a β-ketonitrile to form an olefin, followed by cyclisation with elemental sulfur. K. Gewald, E. Schinke,H. Bottcher; Chem. Ber.; 1966; 99;94.
  • 13. The Hinsberg Synthesis D. The Hinsberg Synthesis: Two consecutive aldol condensations between a 1, 2-dicarbony1 compound and diethy1 thiodiacetates gives thiophene. The immediate product is an ester-acid produced[19] by a Stobbe-type mechanism but the reactions are often worked up via hydrolysis to afford an isolated diacid: H. Wynberg, H. J. Kooreman;J. Ame. Chem. Soc.; 1965;87; 1739
  • 14. GENERAL SYNTHETIC PROCEDURE S A. From thiocarbonyl compounds : 2-Keto-thiols added to alkenyl phosphonium ions followed by ring closure via Witting reaction gives 2, 5- dihydrothiophenes which can be dehydrogenated[20]. J. M. Mclntosh,H. Khalil;Can. J. Chem.; 1975; 53; 209
  • 15. B. Using carbon disulfid: 2-alkylthiophenes[21] can be synthesized by the addition of a carbanion to carbon disulfide with a subsequent S-alkylation. GENERAL SYNTHETIC PROCEDURE S D. Prim,G. Kirsh;Synth. Comm.; 1995;25; 2449
  • 16. C. From thio-nitroacetamides: The S-alkylation of thio-nitroacetamides with 2-bromoketones produces 2-amino-3-nitrothiophenes[22]. GENERAL SYNTHETIC PROCEDURE S D. Prim,G. Kirsh;Synth. Comm.; 1995;25; 2449
  • 17. D. From thiazoles: When thiazoles are heated strongly with an alkyne, generates 2, 5- unsubstituted thiophenes. Though the conditions are vigorous, excellent yield can be obtained GENERAL SYNTHETIC PROCEDURE S W.You, X.Yan, Q. Liao,C. Xi;Org. Lett.; 2010; 12; 3930
  • 18. A.Thiophene can be synthesized on industrial scale by the high temperature reaction between n- butane and Sulfur. SYNTHESIS ON INDUSTRIAL SCALE B.Thiophene can be synthesized by passing a mixtureacetylene and hydrogen sulfide through a tube containing alumina at 400°C.This method is commercially used. W.You, X.Yan, Q. Liao,C. Xi;Org. Lett.; 2010; 12; 3930
  • 19. C.Thiophene may also be prepared by heating sodium succinate with phosphorous trisulphide. SYNTHESIS ON INDUSTRIAL SCALE W.You, X.Yan, Q. Liao,C. Xi;Org. Lett.; 2010; 12; 3930
  • 20. MISCELLANE OUS SYNTHETIC PROCEDURES Various other methods have been reported for synthesizing substituted thiophene. Some of them are as follows: i)Copper-catalyzed tandem S-alkenylation of potassium sulfide with 1, 4-diiodo-1, 3-dienes enables an efficient synthetic approach to variously substituted thiophenes[
  • 21.  ii)An efficient one-step method for the synthesis of highly substituted thiophenes from  thiomorpholides and α-haloketones has been developed[24] MISCELLANE OUS SYNTHETIC PROCEDURES
  • 22.  gold-catalyzed carbothiolation provided an atom-economic way of synthesizing sulfurcontaining heterocycles such as 2,3- disubstituted benzothiophenes[26]. MISCELLANE OUS SYNTHETIC PROCEDURES W.You, X.Yan, Q. Liao,C. Xi;Org. Lett.; 2010; 12; 3930
  • 23. CHEMICAL BEHAVIOUR OF THIOPHENE a. Reactions with oxidizing reagents The thiophene ring system is relatively stable to oxidants and side- chains can be oxidized to carboxylic acid groups. b. Reactions with nucleophilic reagents Nucleophilic displacements proceed atleast hundred times faster than for benzenoid counterparts. F. Freeman, M.Y. Lee, H. Lue, X. Wang, E. Rodriguez;J. Org. Chem.; 1994; 50; 3695
  • 24. c. Reactions with electrophilic reagents 1.Acylation 2.Sulfonation 3.Nitration 4.Halogenation 5.Condsation with Aldehydes and ketone. CHEMICAL BEHAVIOUR OF THIOPHENE
  • 28. Condensation with Aldehydes and ketones: CHEMICAL BEHAVIOUR OF THIOPHENE G. Marino;Tetra.; 1965;21; 843.
  • 29. Thelatest syntheses of thiophene S. Pathania,R. K. Narang, R. K. Rawal Eur. J. Med.Chem. 2019, 180, 486-508.
  • 30. Eur. J. Org.Chem. 36 (2014), 8167-8181, doi:10.1002/ejoc.201403100 Thelatest syntheses of thiophene
  • 31. This journal is ©The Royal Society ofChemistry 2020 Thelatest syntheses of thiophene
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  • 33. Thelatest syntheses of thiophene C. Horn, D. Pospiech,J.Zessin,S. Stein, D. Jehnichen, H. Komber, M. G¨obel, B. Voit andA. Kiriy, Phys.Status SolidiA, 2019, 216, 1800747–1800753.
  • 34. C. H.Tsai, A. Fortney,Y. Qiu, R. R. Gil, D.Yaron, T. Kowalewski and K. J.T. Noonan, J. Am. Chem. Soc., 2016, 138, 6798–6804. Thelatest syntheses of thiophene
  • 35. AdiwishWM,YaacobWA, Adan D, NazlinaI (2012) Synthesis and antibacterialactivityof thiophenes. Int J Adv Sci Eng Inf Tech 2(4):27–30 Thelatest syntheses of thiophene
  • 36. Gunda SR, LingalaS,AllenkiV(2017) Synthesisand anticanceractivityof some novel 3-[(2-substituted-6,7,8,9-tetrahydro-5Hcyclohepta[b]thieno[2,3-d]pyrimidin- 4-yl)amino]propan-1-olderivatives.Eur J Pharm Med Res 4(6):481–484 Thelatest syntheses of thiophene
  • 37. . Mohareb RM, AbdallahAE, HelalMH,ShaloofSM (2016) Synthesisand structure elucidationof some novel thiophene and benzothiophenederivativesas cytotoxicagents. Acta Pharm 66:53–68. Thelatest syntheses of thiophene
  • 38. BIOLOGICAL ACTIVITYAND SOMEASPECTS OF PRACTICAL USEOF THIOPHENE In medicinal chemistry, thiophene derivatives have been very well known for their therapeutic applications. Many thiophene derivatives have been developed as chemotherapeutic agents and are widely used.