Author links open overlay panel bunyarat rungtaweevoranit a akkarapol butsuri a krittaphat wongma a karoon sadorn a. Photochemical polymerization of thiophene derivatives in. Request pdf the synthesis of 3hnaphthol1,8 bcthiophene derivatives methods for the synthesis of keto derivatives of the little studied naphtho1,8bc thiophene system have been developed. Synthesis of thiophene and no curcuminoids for antiinflammatory and anticancer activities. Metalfree synthesis of thiophenes 40 from 1,3diynes 39 and na2s 70. Thieno2,3b thiophene derivatives 1 was converted into the corresponding bromoketone2 85% using br 2 in refluxing acoh for 1 h. This chapter covers aspects of the most recent developments in the synthesis and application of thiophene oligomers and polymers for use in a wide range of fields, from very efficient organic solar cells 2015nc10085 to fluorophores specifically binding amyloid fibrils formed inside neural cells in alzheimers and other neurodegenerative diseases. Molecular structure of thiophene 1,1dioxides, thiophene soxides, and their derivatives article in chemistry of heterocyclic compounds 386. Therapeutic importance of synthetic thiophene springerlink.
Clean and efficient iodination of thiophene derivatives submitted by frederic gohier on fri, 10162015 15. The reaction of either cyclohexanone or cyclopentanone with cyanoacetylhydrazine and elemental sulfur gave the 2aminocycloalkenobthiophene derivatives 3a and 3b, respectively. Download limit exceeded you have exceeded your daily download allowance. The synthesis of thiopene derivatives from diacetylenic hydrocarbons has been described 1. Solventfree and liquid phase iodination of thiophene derivatives with potassium. Hoffman department of biochemistry, purdue university, lafayette, indiana 47907 u. Synthesis of thiophenecontaining conjugated polymers from. The rate of halogenation of thiophene at 25 c is about 10 8 times that of benzene. Pdf synthesis and characterization of new thieno3,2b. Chuong tusy, lili huang, jingpeng jin, jiangbin xia college of chemistry and molecular science, wuhan university, wuhan 430072, china. Similarly, 5nitrothiophene2aldehyde gives 5nitro2thenylidenepaminobenzoic acid and 5nitro2thenylidenebarbituric acid.
Solidstate synthesis of a conducting polythiophene via an unprecedented heterocyclic coupling reaction. The synthesis of brdntt features chemoselective metalation and crosscoupling reactions that enable us to keep the 2bromo group intact from the starting material. Articaine6 is the most commonly used dental anesthetic in europe, and patrin27 is an inhibitor of the dna. They occur in coal tar distillates the discovery of thiophene in coaltar benzene provides one of the classic anecdotes of organic chemistry. Of the iron and molybdenum compounds examined in the present study fecl3, febr2, feoac2, feacac 3, moo3, mocl5, moco6, feacac 3 and moco6 proved to be most efficient in this reaction. Synthesis of new thiophene derivatives and their use as photostabilizers for rigid polyvinyl chloride january 2015 international journal of polymer science 20151. Synthesis and investigation of novel thiophene derivatives containing heteroatom linkers for solid state polymerization. Phenylenethiophene oligomer derivatives for thinfilm transistors. Synthesis of new thiophene derivatives and their use as photostabilizers for rigid polyvinyl chloride. Pdf synthesis and characterization of the novel thiophene.
Condensation of thiophene2aldehyde with paminobenzoic and barbituric acids gives 2thenylidene paminobenzoic acid and 2thenylidenebarbituric acid. Article views are the countercompliant sum of full text article downloads since november 2008 both pdf and html across all institutions and individuals. Fivemembered rings with one heteroatom together with their benzo and other carbocyclicfused derivatives. Electronic properties were evaluated by uvvis, cyclic voltammogram, and theoretical calculations. Articaine6 is the most commonly used dental anesthetic in. Thiophene, when compared with 1,4disubstituted benzene units. Thiophene has been selected because of its stability and versatility in lending itself to synthetic modification and hence forms links in chain structures for rodlike.
Pdf synthesis of new thiophene derivatives and their use as. Recent advances in the synthesis of thiophene derivatives by. Synthesis of thiophenecontaining conjugated polymers from 2. Synthesis of some thiophene derivatives springerlink. Convenient and improved methods of synthesis afforded dyes 5 and 7 in higher yields metal free ethynylbithiophene or ethynylthieno3,2bthiophene dyes for dssc. A formal thioboration and subsequent sulfur dealkylation provide 3. The solvent is evaporated and the residue is washed with h 2 o 20 ml and diethyl ether 5 ml, yielding the corresponding thiophene and benzobthiophene hydrazide derivatives 5ag, 6ag. Synthesis and characterization of new thieno3,2bthiophene derivatives article pdf available in molecules 1710. Synthesis and applications of thiophene derivatives as. A series of ethyl2substituted benzylideneamino4,5,6,7tetrahydrobenzob thiophene 3carboxylate derivatives were synthesized by using gewald synthesis and their structures were confirmed by ftir, ms and 1hnmr. Synthesis of novel derivatives of carbazolethiophene, their. The setback of drug resistance and generation of free radicals has promoted the researchers to study and explore for new compounds to combat.
Synthesis, reactions and biological activity of some new bis heterocyclic ring compounds containing sulphur atom. Synthesis of thiophene2thiol derivatives springerlink. Scientific paper new approaches for the synthesis of thiophene derivatives with antitumor activities rafat m. Similarly, 5nitro thiophene 2aldehyde gives 5nitro2thenylidenepaminobenzoic acid and 5nitro2thenylidenebarbituric acid. Synthesis and cytotoxicity of fused thiophene and pyrazole.
Introduction thiophene is a heterocyclic compound with formula c4h4s, it is colorless and has a mildly pleasant odor at room temperature. As a primary step to develop novel sidechain liquid crystalline conductive polythiophenes, we have synthesized a series of monosubstituted thiophene derivatives with phenylalkyl, phenoxyalkyl, and phenoxycyclohexyl group as a substituent and then polymerized them through chemical polymerization procedure. Our objective is to arouse curiosity and interest in thiophene derivatives as organic materials and furnish some basic information and references useful to the reader as a trace to deepen the knowledge on the topics that heshe will consider most important. New sulfides of the thiophene series were synthesized by reaction of thiophene 2thiol with compounds containing active halogen atoms and double bonds. Hinsberg thiophene synthesis an overview sciencedirect. Ibrahim3 1 departrment of chemistry, faculty of science, cairo university, giza, a.
Conclusions three new thiophene derivatives were synthesized. Synthesis and investigation of novel thiophene derivatives. A method is proposed for the synthesis of 5acylamino2,3dimethylthiophene4carbaldehydes and 5acylamino2,3tetramethylenethiophene4carbaldehydes by the formylation of the corresponding thiophenes using the vilsmeier reaction. Synthesis and antibacterial activity of novel thiophene derivatives. Jn are the arsenic derivatives of thiophene prepared by finzi12345 and steinkopf6 in these cases arsenic is substituted in one \ of the alpha positions whereas the other alpha position is 1 occupied by h, br, i, or ch3, all positive groups. Thus, in this paper, we would like to present an efficient metalfree synthesis of the.
A thiophene derivative from 1,2,3,5tetraoacetyl4thio. Synthesis of thiophene derivatives by iodocyclization of scontaining. New method for the synthesis of 2thiophenecarboxylic acids. Synthesis of benzothiophene and indole derivatives through. A new series of thiophene analogues was synthesized and checked for their in vitro antibacterial, antifungal, antioxidant, anticorrosion and anticancer activities. We have examined for the first time the reaction of diacetylenic diesters with hydrogen sulfide and with nahs. Pdf new thiophene derivatives as antimicrobial agents. Molecular structure of thiophene 1,1dioxides, thiophene s. New sulfides of the thiophene series were synthesized by reaction of thiophene2thiol with compounds containing active halogen atoms and double bonds. Thiophene has been selected because of its stability and versatility in lending itself to synthetic modification and hence forms links in chain structures for rodlike metallomesogens. Structure and semiconductor performances zongfan duan1.
The latter reacted with hydrazine hydrate to give the hydrazine derivative 5 which was used to form the hydrazone derivatives 7a, b and 9a, b via its reaction with some carbonyl compounds. New approaches for the synthesis of thiophene derivatives with antitumor activities. Synthesis of novel derivatives of carbazolethiophene. Thiocyanation of 2acylaminothiophenes and synthesis of thieno2,3dthiazoles. Synthesis and characterization of pushpull bithiophene and. Thiophene belongs to a class of heterocyclic compounds containing a five membered ring made up of one sulphur as heteroatom with the formula c 4 h 4 s. The nitration of 2formylthiophene, 2acetothienone, and unsaturated ketones of the thiophene series with copper and aluminum nitrates in acetic anhydride at various temperatures was studied. Thiophene and bioisostere derivatives as new mmp12 inhibitors.
Solidstate synthesis of a conducting polythiophene via an. The diacetylenic diesters react readily with hydrogen sulfide or nahs in acetone at ph 910 to give 2,5disubstituted thiopheries see table 1. Spectrum chemical offers fine chemicals in lab and production sizes. Synthesis of thiophene derivatives and their antimicrobial. Synthesis of new thiophene and benzobthiophene hydrazide. Synthesis of new thiophene derivatives and their use as. Zhang a1, zhou g, rong sb, johnson km, zhang m, kozikowski ap. Rapososynthesis and characterization of novel thieno3,2bthiophene based metal free organic dyes with different heteroaromatic donor moieties as sensitizers for dyesensitized solar cells. In p1p9, carbazolethiophenes were linked at the n9 position for different core groups via biphenyl, dimethylbiphenyl, and phenyl. Halogenation of thiophene occurs very readily at room temperature and is rapid even at.
In conclusion, a series of carbazolethiophene derivatives p4p9 were prepared by means of suzukimiyaura and ullmann coupling reactions as key steps. Synthesis and characterization of pushpull bithiophene. Structureperformance relationship was studied with the aid of theoretical calculation. Thiophene derivatives with multiple substitutions are prepared from vinylidene bromide, which is synthesized by the reaction of thiophene 2carboxaldehyde with carbon tetrabromide in the presence of pph 3, as a core molecule through several coupling reactions such as suzukimiyaura coupling and palladiumcatalyzed ch arylation. Condensation of thiophene 2aldehyde with paminobenzoic and barbituric acids gives 2thenylidene paminobenzoic acid and 2thenylidenebarbituric acid. High molecular weight thiophene containing conjugated polymers were successfully synthesized by suzuki polycondensation of aryl dibromides and 2,5thiophenebisboronic acid derivatives by using a new thiophene containing bulky phosphorous compound as the ligand for a zerovalent palladium catalyst. Synthesis of arylsubstituted thieno3,2bthiophene derivatives and their use for n,sheterotetracene construction. Clean and efficient iodination of thiophene derivatives.
Pdf synthesis of new thiophene derivatives and their use. Description since thiophene very often yields compounds that are analogous to benzene derivatives in general physiological properties, it was decided to attempt to prepare the nitro and amino derivatives of 1,1,1trichloro2,2bis2thienylethane v as well as the nitro and amino derivatives of 2,2,3. Our objective is to arouse curiosity and interest in thiophene derivatives as organic materials and furnish some basic. Condensation of thiophene2aldehyde with nitroethane gives 12thienyl2nitroprop1ene. Condensation of thiophene 2aldehyde with nitroethane gives 12thienyl2nitroprop1ene. Pdf thiophene and pyrrole derivative polymers electro. From the formyl derivatives obtained, previously unaccessible derivatives of thieno2,3bpyridine, thieno2,3dpyrimidine, and thieno3.
This study involves the synthesis and structural characterization of new metal complexes of thiophene derivatives that have potential liquid crystalline properties. Phenylenethiophene oligomer derivatives for thinfilm. New method for the synthesis of 2thiophenecarboxylic. Synthesis, reactions and biological activity of some new.
Cyanoacetamide derivatives as synthons in heterocyclic synthesis. Synthesis and proton nmr spectra in the 2aminothiophene series, chemischer informationsdienst, 1981, 12, 51wiley online library. Synthesis of thiophene derivatives via palladiumcatalyzed. A facile twostep synthesis of thiophene endcapped aromatic systems. Thiophene has been selected because of its stability and versatility in lending itself to synthetic modification. Nitration of thiophene analogs of ddt unt digital library. As a primary step to develop novel sidechain liquid crystalline conductive polythiophenes, we have synthesized a series of monosubstituted thiophene derivatives with phenylalkyl, phenoxyalkyl, and phenoxycyclohexyl group as a substituent and then polymerized them. Synthesis of thiophene derivatives containing a ferrocenyl radical. Thiophene definition of thiophene by medical dictionary. Solventfree and liquidphase iodination of thiophene derivatives. The thiocyanation of 5acylaminothiophenes gives 4thiocyanato derivatives, the intramolecular cyclization of which gives 2acylaminothieno2,3d.
New approaches for the synthesis of thiophene derivatives. The synthesis of 3hnaphthol1,8bcthiophene derivatives. Thiophene and pyrrole derivative polymers electrosynthesized on stainles steel. Complexes of thiophene derivatives as potential metallomesogens. Chemical communication 2004 19, 2222 2223 photochemical polymerization of thiophene derivatives in aqueous solution sergey a. A series of carbazolethiophene dimers, p1p9, were synthesized using suzukimiyaura and ullmann coupling reactions. The reaction of either cyclohexanone or cyclopentanone with cyanoacetylhydrazine and elemental sulfur gave the 2aminocycloalkenob thiophene derivatives 3a and 3b, respectively. Thiophene is taken from the word theion, the greek word for sulfur, and another greek word phaino which means shinning.
The desired product was obtained by filtration, washed with water, dried well and recrystallized. Synthesis of thiophenecapped 2rotaxanes pdf free download. High molecular weight thiophenecontaining conjugated polymers were successfully synthesized by suzuki polycondensation of aryl dibromides and 2,5thiophenebisboronic acid derivatives by using a new thiophenecontaining bulky phosphorous compound as the ligand for a zerovalent palladium catalyst. Thiophene and its derivatives exist in petroleum or coal. Looking for online definition of thiophene in the medical dictionary.
The reactions with a wide variety of organic halides lead to a. Synthesis and some properties of bisruthenocenylthiophene derivatives possible spincoupling in the twoelectron oxidized. This spectrum integrates for 10 protons, and is composed of three singlet signals. At low temperatures 2acetothienone gives a mixture of 4 and 5nitro isomers, while 2formylthipphene gives only a 5nitrosubstituted compound in the diacetate form. Carbohydrate research 7 note a thiophene derivative frorn 1,2,3,6tetra0acetyl 4thiodribofuranose r. Four linear oligothiophenes containing 4, 5 and 7 thiophene rings substituted by a variable number of octyl chains attached at the betaposition of some of the thiophene rings and possessing a. In a simple, regiocontrolled, and transitionmetal free approach to access exclusively 3borylated thiophene derivatives, commercially available bchlorocatecholborane acts as a carbophilic lewis acid to activate the alkyne in readily synthesized zorganylthioenyne substrates. Synthesis of ringfluorinated thiophene derivatives based on single cf bond activation of cf 3cyclopropanes.
Moreover, it produced the pyrazole derivatives 11a, b through its. Pdf thiophene and bioisostere derivatives as new mmp12. Thus the synthesis and characterization of novel thiophene moieties with wider therapeutic activity is a topic of interest for the medicinal chemist. Otherwise, in those cases, where the thiophene soxide does not exhibit a ch 3 substituent on the ring system, furans are often the main products along with deoxygenated thiophenes scheme 39. Received march 7th, 1969 during the course of synthesis of a nucleoside by condensation of 2,3,5tri0acetyl4thiodr. The electronic structures were determined by uvvis, fluorescence spectral measurements, cv, and theoretical calculations. Using thiophene as an example, it was demonstrated that the reaction is catalyzed not only by voacac2 but also by iron and molybdenum compounds. Pdf the use of thiophene derivatives that have a stable structure in agriculture, food and pharmaceutical. A thiophene derivative from 1,2,3,5tetraoacetyl4thiod. Chapter three synthesis and applications of thiophene derivatives as organic materials.
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