- Continuous Flow Synthesis of 2H-Thiopyrans via thia-Diels–Alder Reactions of Photochemically Generated Thioaldehydes
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Herein, we report a novel protocol for the photochemical generation of thioaldehydes in a continuous flow process which were in situ reacted with electron rich 1,3-butadienes in thia-Diels–Alder reactions. A broad range of 3,6-dihydro-2H-thiopyrans were formed as products in much higher yields and productivities as compared to classical batch processes. Moreover, greatly reduced reaction times and a facile large-scale preparation of products were achieved by fully exploiting the advantages of continuous flow technology.
- Sachse, Florian,Gebauer, Konrad,Schneider, Christoph
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- Synthesis of Phenanthro[9,10-c]thiophenes by 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)-Promoted Cyclo-Oxidation
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A new method to prepare phenanthro[9,10-c]thiophenes has been developed. In the presence of triflic acid, 3,4-diaryl thiophenes undergo 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)-promoted cyclo-oxidation. NMR and computational studies indicate that p
- Gao, Han,Connors, David M.,Goroff, Nancy S.
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p. 630 - 633
(2019/05/21)
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- Synthesis of Thioethers Using Triethylamine-Activated Phosphorus Decasulfide (P410
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The synthesis of thioethers in excellent yields was achieved under mild conditions via the displacement reaction of halogens by sulfur. The cross-reaction of 2-(α-bromoacetyl)thiophene with triethylamine-activated phosphorus decasulfide (Et3N-P2S5) was elaborated by utilizing DFT calculations.
- Turkoglu, Gulsen,Cinar, M. Emin,Ozturk, Turan
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p. 3618 - 3624
(2016/10/17)
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- Thiophene synthesis via 1,1-carboboration
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Reaction of bis(tert-butylethynyl)sulfide with the boron Lewis acid reagents X-B(C6F5)2 (X = CH3, Cl, C6F5) in pentane at r.t. gave the respective borylated thiophenes in a sequence of 1,1-
- Eller, Christina,Kehr, Gerald,Daniliuc, Constantin G.,Stephan, Douglas W.,Erker, Gerhard
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supporting information
p. 7226 - 7229
(2015/04/27)
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- Stereoselective synthesis of cis-2,6-disubstituted morpholines and 1,4-oxathianes by intramolecular reductive etherification of 1,5-diketones
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A simple and efficient, Lewis acid catalysed reductive etherification strategy for the stereoselective synthesis of cis-2,6- disubstituted morpholines and 1,4-oxathianes starting from readily available 1,5-diketones has been developed. The strategy is used in the total synthesis of morpholine-based natural products (±)-chelonin A and formal total synthesis of (±)-chelonin C.
- Gharpure, Santosh J.,Anuradha, Dandela,Prasad, Jonnalagadda V. K.,Rao, Pidugu Srinivasa
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- One-pot preparation of arylethynyl sulfides and bis(arylethynyl) sulfides
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An efficient preparation for arylethynyl sulfides 1 and bis(arylethynyl) sulfides 2 has been accomplished through a one-pot, three-step strategy that starts from arylethanonyl sulfides and bis(arylethanonyl) sulfides, respectively, without the use of various terminal arylacetylenes as substrates. When lithium hexamethyldisilazane (LHMDS), ClP(O)(OEt)2, and LHMDS were sequentially added to a tetrahydrofuran solution of different substrates [arylethanonyl sulfides or bis(arylethanonyl) sulfides], 1 or 2 were obtained in moderate to good yields. The reaction procedure involves the formation of an enol phosphate and a subsequent base-induced elimination. An efficient preparation of arylethynyl sulfides 1 and bis(arylethynyl) sulfides 2 has been accomplished by a one-pot, three-step strategy that starts from arylethanonyl sulfides and bis(arylethanonyl) sulfides, respectively, to give 1 and 2 in moderate to good yields. The reaction mechanism involves the formation of an enol phosphate that undergoes a subsequent base-induced elimination. Copyright
- Su, Qiong,Zhao, Zi-Jian,Xu, Feng,Lou, Peng-Cai,Zhang, Kai,Xie, De-Xun,Shi, Lei,Cai, Qing-Yun,Peng, Zhi-Hong,An, De-Lie
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p. 1551 - 1557
(2013/04/23)
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- Asymmetric synthesis of chiral dihydrothiopyrans via an organocatalytic enantioselective formal thio [3 + 3] cycloaddition reaction with binucleophilic bisketone thioethers
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An unprecedented organocatalytic highly enantioselective approach to a 3,4-dihydro-2H-thiopyran scaffold with two contiguous stereogenic centers has been implemented through a formal thio [3 + 3] cycloaddition process involving a Michael-aldol condensation cascade sequence. Notably, a new class of binucleophilic bisketone thioethers is designed for the process. Furthermore, the fine-tuning of their reactivity enables the cascade process to proceed with highly regioselectively.
- Wang, Shengzheng,Zhang, Yongqiang,Dong, Guoqiang,Wu, Shanchao,Zhu, Shiping,Miao, Zhenyuan,Yao, Jianzhong,Li, Hao,Li, Jian,Zhang, Wannian,Sheng, Chunquan,Wang, Wei
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supporting information
p. 5570 - 5573
(2013/11/19)
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- An aquatic pseudo-four-component reaction for the synthesis of highly substituted thiophenes
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A novel and simple procedure was developed for the construction of fully substituted thiophenes. A series of α-haloacetophenone derivatives were converted into fully substituted thiophenes by treatment with sodium sulfide in the presence of 1,8-diazabicyc
- Zali-Boeini, Hassan,Ghani, Maryam
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p. 913 - 918
(2013/05/08)
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- Synthesis of oxathiane and morpholine from acyclic precursors: A modified Mitsunobu reaction
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Synthesis of a set of isomeric 2,4,6-triarylmorpholines and 2,6-diaryloxathianes from the corresponding 1,5-diols has been described. The method provides an efficient route to six-membered heterocycles from acyclic diols and is found to be better than Mitsunobu procedure in yield and waste management. In a related study, the ring contraction of pyranone to two isomeric cyclopentenone derivatives through Nazarov reaction has been noticed.
- Paul, Nidhin,Kaladevi, Selvam,Beneto, Arockiam Jesin,Muthusubramanian, Shanmugam,Bhuvanesh, Nattamai
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p. 6892 - 6901
(2012/09/11)
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- Synthesis of novel N-hydroxy heterocycles via intramolecular reductive cyclization of diketoximes by NaBH3CN
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A simple and efficient protocol for the construction of substituted piperazines, piperidines, thiomorpholines, decahydroquinolines, perhydrocyclopenta[b]pyridine, and pyrrolidines bearing N-hydroxy substituents through intramolecular reductive cyclization of diketoximes using sodium cyanoborohydride is described.
- Nagaraj, Muthupandi,Boominathan, Muthusamy,Muthusubramanian, Shanmugam,Bhuvanesh, Nattamai
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body text
p. 4642 - 4652
(2011/07/29)
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- Convenient synthesis of symmetrical diketosulfides from enolizable ketones using [hydroxy(tosyloxy)iodo]benzene and Na2S·9H20
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An efficient method for the preparation of symmetrical diketosulfides of the type ArCOCH2SCH2COAr has been developed from the reaction of [hydroxy(tosyloxy)iodo]benzene with various acetophenones, followed by treatment with Na2
- Karade, Nandkishor N.,Tiwari, Girdharilal B.,Gampawar, Sumit V.,Shinde, Sandeep V.
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experimental part
p. 172 - 176
(2009/09/30)
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- A new class of sulfur-linked bis-1,2,3-selenadiazoles, 1,2,3-thiadiazoles, and 2H-diazaphospholes
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Novel sulfur-linked bis-heterocycles, bis-1,2,3-selenadiazoles 4, 1,2,3-thiadiazoles 5, and 2H-diazaphospholes 1, were synthesized from bis(2-oxo-2-phenylethanone)sulfide 2 by adopting a simple and well-versed methodology.
- Padmavathi, Venkatapuram,Mahesh, Konda,Subbaiah, Dandu Rangayapalle Chinna Venkata,Padmaja, Adivireddy
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p. 261 - 265
(2008/09/19)
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- One-pot oxidation and bromination of 3,4-diaryl-2,5-dihydrothiophenes using Br2: Synthesis and application of 3,4-diaryl-2,5-dibromothiophenes
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(Chemical Equation Presented) A class of 3,4-diaryl-2,5-dibromothiophenes (1b-5b) was synthesized by a one-pot reaction of 3,4-diaryl-2,5- dihydrothiophenes with Br2 reagent in excellent yield (83-92%). It was found that Br2 performed a double function (oxidation and bromination) during the conversion of 3,4-diaryl-2,5-dihydrothiophenes to 3,4-diaryl-2,5-dibromothiophenes. The application of 3,4-diaryl-2,5- dibromothiophenes used as building blocks was also investigated. Employing 3,4-diphenyl-2,5-dibromothiophene (1b) as a template, a class of 2,3,4,5-tetraarylthiophenes was prepared by the Suzuki coupling reaction. This provided a new and simple approach to the preparation of 2,3,4,5- tetraarylthiophenes.
- Dang, Yizhe,Chen, Yi
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p. 6901 - 6904
(2008/02/11)
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- Oxidation of 3,4-diaryl-2,5-dihydrothiophenes to 3,4-diarylthiophenes using CuBr2: Simple and efficient preparation of 3,4-diarylthiophenes
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A class of 3,4-diarylthiophenes was prepared in excellent yield (80-91%) by oxidation of 3,4-diaryl-2,5-dihydrothiophenes with CuBr2. The approach is also available for the synthesis of 3,4-diarylpyrroles and 3,4-diarylfuran. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
- Dang, Yizhe,Chen, Yi
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p. 5661 - 5664
(2008/09/17)
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- Synthesis of 3,4-diphenyl-substituted poly(thienylene vinylene), low-band-gap polymers via the dithiocarbamate route
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It has been demonstrated that the dithiocarbamate precursor route is a suitable pathway towards poly(thienylene vinylene) (PTV)-type low-band-gap polymers. Two particular dithiocarbamate precursor polymers and the corresponding conjugated polymers, poly(3,4-diphenyl-2,5-thienylene vinylene) and poly(3,4-bis(4-butylphenyl)-2,5-thienylene vinylene), have been studied. The introduction of butyl side chains in the latter leads to excellent solubility in common organic solvents. Both polymers have been prepared in a straightforward manner and in good yield. The thermal conversion of the precursor polymers into the conjugated structure was studied with in situ FT-IR and UV-vis spectroscopy. Also, with the latter technique, the band gap was determined and the thermochromic effect was studied and compared with the unsubstituted PTV. The HOMO and LUMO levels of the polymers were determined from UV-vis and electrochemical measurements.
- Henckens,Colladet,Fourier,Cleij,Lutsen,Gelan,Vanderzande
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- Mechanism-based design of simple, symmetrical, easily prepared, potent antimalarial endoperoxides
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Mechanism-based design, two-step synthesis, and in vitro antimalarial testing showed thermally stable, crystalline, bicyclic endoperoxides 2a and 2b to be potent antimalarials. Their reduction by FeBr2 proceeds via oxy-radicals and then carbon
- Posner, Gary H.,Wang, Dasong,Gonzalez, Lluisa,Tao, Xueliang,Cumming, Jared N.,Klinedinst, Donna,Shapiro, Theresa A.
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p. 815 - 818
(2007/10/03)
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- Sulfuranes with Oximate Axial Ligands
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New sulfuranes having one or two axial oximate (R2C=NO) ligands were synthesized.An improved sulfurane-forming step, involving a rapidly stirred suspension of NaHCO3, is described.The failure of sulfide oximes in which sulfur bears one or two tertiary carbons to form sulfuranes is explained by a C-S bond cleavage leading to tertiary carbocations.This represents a hitherto unanticipated limitation to the standard method of sulfurane synthesis.The X-ray crystal structure of one of the new sulfuranes, namely 2,2'-spirobi(4-phenyl-3H-1,2,5-oxathiazoline), is reported (R = 0.0368).An unusual feature was the quite compressed equatorial (C-S-C) angle, 102.6(1) deg.The S-O bond length, 1.846(2) Angstroem, was similar to S-O bond lenghths of sulfuranes having two axial carboxylate ligands.Since the oximate ligand has not been used previously in a 10-S-4 species, an assessment of its apicophilicity relative to other more common axial ligands was made by considering X-ray structural data, IR data, and ab initio calculations.These suggest that the R2C=NO ligand is as apicophilic as the hexafluorocumyloxy (ArC(CF3)2O) ligand.
- Hornbuckle, S. F.,Livant, P.,Webb, T. R.
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p. 4153 - 4159
(2007/10/02)
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- CYANO AND FLUORODESTANNYLATION: A NEW METHODOLOGY USING SOME POWERFUL SULFUR TRANSFER REAGENTS, THE ORGANOTIN SULFIDES
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Fluoride and cyanide ions destannylate bis(aralkyl)tin sulfides and trialkyltin sulfides giving, in the presence of a variety of alkyl and activated halides, the corresponding thioether derivatives in excellent yield.The conditions are mild, neutral and anhydrous; a strong solvent effect is noted.Special comments are made concerning work-up procedures.
- Harpp, David N.,Gingras, Marc
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p. 4373 - 4376
(2007/10/02)
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- Bis(tributyltin) Sulfide: An Effective and General Sulfur-Transfer Reagent
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Bis(tributyltin) sulfide acts efficiently to transfer the sulfur atom as S(2-) to a variety of halide substrates to afford the corresponding symmetrical sulfides in good overall yield.
- Harpp, David N.,Gingras, Marc,Aida, T.,Chan, T. H.
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p. 1122 - 1124
(2007/10/02)
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- 7-Alkylation and 7-Sulphonylation of 5,6-Dihydroimidazolo-thiazoles
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Reinvestigation of the alkylation of 3-phenyl-5,6-dihydroimidazolothiazole has shown that methylation occurs exclusively at the 7-position, and that the free base is readily solvolysed to a mixture of 1-methylimidazolidin-2-one, 1-methylimidazolidine-2-thione, and diphenacyl sulphide and disulphide. 3-Methyl-5,6-dihydroimidazolothiazole with methane- and arene-sulphonyl chlorides gave the corresponding 7-sulphonylthiazolium chlorides.On heating, these rearranged to 3-(2-chloroethyl)-4-methyl-3-aryl (or alkyl)sulphonylimido-2,3-dihydrothiazoles.The 7-(4-chlorophenylsulphonyl) derivative lost this substituent with aqueous base while concentrated aqueous ammonia attacked the 7a-position leading to a 3--2-imino-4-methyl-2,3-dihydrothiazole.
- Acheson, R. Morrin,Cooper, Martin W.,Cox, Ian R.
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p. 1773 - 1778
(2007/10/02)
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- Facile Syntheses of 1,4,5-Thiadiazepine, 1,4,7-Thiadiazonine, Imidazothiazine and Pyrimidothiazine
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The condensation of diphenacyl sulphides with hydrazine hydrate, 1,2-diaminoethane, 1,2-diaminopropane and 1,3-diaminopropane, performed in ethylene glycol-ethanol (3: 2) medium provides convenient syntheses of 3,6-diaryl-2,7-dihydro-1,4,5-thiadiazepine (
- Sandhu, S. S.,Tandon, S. S.,Singh, Harjit
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p. 1023 - 1027
(2007/10/02)
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