- 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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- 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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scheme or table
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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- 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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- 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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