The Experts below are selected from a list of 1269 Experts worldwide ranked by ideXlab platform
Dongju Zhang - One of the best experts on this subject based on the ideXlab platform.
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transition metal free one pot synthesis of fused 1 4 thiazepin 5 4h ones and theoretical study of the s n type Smiles Rearrangement process
Journal of Organic Chemistry, 2014Co-Authors: Bingchuan Yang, Shunwei Chen, Zeyuan Zhang, Dongju ZhangAbstract:A series of 1,4-thiazepin-5(4H)-one derivatives were synthesized via a transition metal-free one-pot Smiles Rearrangement process at room temperature. Regioselective seven-membered heterocycles were constructed in good to excellent yields. To gain an in-depth understanding of the S–N type Smiles Rearrangement mechanism, a theoretical study was also performed by quantum chemistry calculations.
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Transition Metal-Free One-Pot Synthesis of Fused 1,4-Thiazepin-5(4H)‑ones and Theoretical Study of the S–N Type Smiles Rearrangement Process
2014Co-Authors: Bingchuan Yang, Caixia Xie, Xiaochen Tan, Ruiying Guo, Shunwei Chen, Zeyuan Zhang, Xianglong Chu, Dongju ZhangAbstract:A series of 1,4-thiazepin-5(4H)-one derivatives were synthesized via a transition metal-free one-pot Smiles Rearrangement process at room temperature. Regioselective seven-membered heterocycles were constructed in good to excellent yields. To gain an in-depth understanding of the S–N type Smiles Rearrangement mechanism, a theoretical study was also performed by quantum chemistry calculations
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a novel dbu promoted s n type Smiles Rearrangement reaction under controlled microwave heating
Tetrahedron Letters, 2007Co-Authors: Qun Zhang, Kai Ding, Liang Xin, Dongju ZhangAbstract:Abstract A convenient process for the preparation of pyrido[1,4]thiazinone derivatives is described in the presence of DBU as base under controlled microwave heating. This process allows for efficient construction of thiazinone-fused pyridine by S–N-type Smiles Rearrangement methodology.
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A novel DBU-promoted S–N-type Smiles Rearrangement reaction under controlled microwave heating
Tetrahedron Letters, 2007Co-Authors: Qun Zhang, Kai Ding, Liang Xin, Dongju ZhangAbstract:Abstract A convenient process for the preparation of pyrido[1,4]thiazinone derivatives is described in the presence of DBU as base under controlled microwave heating. This process allows for efficient construction of thiazinone-fused pyridine by S–N-type Smiles Rearrangement methodology.
Yanli Liu - One of the best experts on this subject based on the ideXlab platform.
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a tandem coupling Smiles Rearrangement cyclization approach to 1 4 benzooxazinones or 1 4 pyridooxazinones under mild conditions
RSC Advances, 2012Co-Authors: Chunjing Zhan, Jiong Jia, Bingchuan Yang, Aiping Huang, Yanli LiuAbstract:A facile and efficient approach to 1,4-benzooxazinone or 1,4-pyridooxazinone scaffolds is developed via Smiles Rearrangement tandem reaction. 1,4-Benzooxazinones or 1,4-pyridooxazinones with diversity at two substituents on their scaffolds were synthesized conveniently in the presence of cesium carbonate at room temperature in good to excellent yields. The reaction mechanism is assumed by a tandem coupling/Smiles Rearrangement/cyclization process.
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One-Pot Synthesis of Fused Pyridazino[4,5-b][1,4]oxazepine-diones via Smiles Rearrangement.
ChemInform, 2012Co-Authors: Yanli Liu, Chunjing Zhan, Aiping HuangAbstract:A convenient synthesis of title compounds (III) from salicyclamides and dichloropyridazinone (II) is achieved by a one-pot coupling/Smiles Rearrangement/cyclization.
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One-Pot Synthesis of Fused Pyridazino[4,5-b][1,4]oxazepine-diones via Smiles Rearrangement
Synlett, 2012Co-Authors: Yanli Liu, Chunjing Zhan, Aiping HuangAbstract:Fused pyridazino[4,5-b][1,4]oxazepine-diones were easily obtained in moderate to excellent yields via Smiles Rearrangement. The synthetic approach is supported by a one-pot couplingSmiles Rearrangement-cyclization process. This process has potential applications in the synthesis of biologically and medicinally relevant compounds.
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A tandem coupling/Smiles Rearrangement/ cyclization approach to 1,4-benzooxazinones or 1,4-pyridooxazinones under mild conditions
RSC Advances, 2012Co-Authors: Chunjing Zhan, Jiong Jia, Bingchuan Yang, Aiping Huang, Yanli LiuAbstract:A facile and efficient approach to 1,4-benzooxazinone or 1,4-pyridooxazinone scaffolds is developed via Smiles Rearrangement tandem reaction. 1,4-Benzooxazinones or 1,4-pyridooxazinones with diversity at two substituents on their scaffolds were synthesized conveniently in the presence of cesium carbonate at room temperature in good to excellent yields. The reaction mechanism is assumed by a tandem coupling/Smiles Rearrangement/cyclization process.
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Regioselective synthesis of fused oxazepinone scaffolds through one-pot Smiles Rearrangement tandem reaction.
ACS combinatorial science, 2011Co-Authors: Yanli Liu, Aiping Huang, Chunxiao Chu, Chunjing ZhanAbstract:The paper describes a convenient and facile methodology for the regioselective synthesis of fused oxazepinone scaffolds. This process is an efficient construction of the oxazepinone scaffold by a one-pot coupling/Smiles Rearrangement/cyclization approach. This transition metal-free process has potential applications in the synthesis of biologically and medicinally relevant compounds.
Bingchuan Yang - One of the best experts on this subject based on the ideXlab platform.
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transition metal free one pot synthesis of fused 1 4 thiazepin 5 4h ones and theoretical study of the s n type Smiles Rearrangement process
Journal of Organic Chemistry, 2014Co-Authors: Bingchuan Yang, Shunwei Chen, Zeyuan Zhang, Dongju ZhangAbstract:A series of 1,4-thiazepin-5(4H)-one derivatives were synthesized via a transition metal-free one-pot Smiles Rearrangement process at room temperature. Regioselective seven-membered heterocycles were constructed in good to excellent yields. To gain an in-depth understanding of the S–N type Smiles Rearrangement mechanism, a theoretical study was also performed by quantum chemistry calculations.
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Transition Metal-Free One-Pot Synthesis of Fused 1,4-Thiazepin-5(4H)‑ones and Theoretical Study of the S–N Type Smiles Rearrangement Process
2014Co-Authors: Bingchuan Yang, Caixia Xie, Xiaochen Tan, Ruiying Guo, Shunwei Chen, Zeyuan Zhang, Xianglong Chu, Dongju ZhangAbstract:A series of 1,4-thiazepin-5(4H)-one derivatives were synthesized via a transition metal-free one-pot Smiles Rearrangement process at room temperature. Regioselective seven-membered heterocycles were constructed in good to excellent yields. To gain an in-depth understanding of the S–N type Smiles Rearrangement mechanism, a theoretical study was also performed by quantum chemistry calculations
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a tandem coupling Smiles Rearrangement cyclization approach to 1 4 benzooxazinones or 1 4 pyridooxazinones under mild conditions
RSC Advances, 2012Co-Authors: Chunjing Zhan, Jiong Jia, Bingchuan Yang, Aiping Huang, Yanli LiuAbstract:A facile and efficient approach to 1,4-benzooxazinone or 1,4-pyridooxazinone scaffolds is developed via Smiles Rearrangement tandem reaction. 1,4-Benzooxazinones or 1,4-pyridooxazinones with diversity at two substituents on their scaffolds were synthesized conveniently in the presence of cesium carbonate at room temperature in good to excellent yields. The reaction mechanism is assumed by a tandem coupling/Smiles Rearrangement/cyclization process.
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A tandem coupling/Smiles Rearrangement/ cyclization approach to 1,4-benzooxazinones or 1,4-pyridooxazinones under mild conditions
RSC Advances, 2012Co-Authors: Chunjing Zhan, Jiong Jia, Bingchuan Yang, Aiping Huang, Yanli LiuAbstract:A facile and efficient approach to 1,4-benzooxazinone or 1,4-pyridooxazinone scaffolds is developed via Smiles Rearrangement tandem reaction. 1,4-Benzooxazinones or 1,4-pyridooxazinones with diversity at two substituents on their scaffolds were synthesized conveniently in the presence of cesium carbonate at room temperature in good to excellent yields. The reaction mechanism is assumed by a tandem coupling/Smiles Rearrangement/cyclization process.
Chunjing Zhan - One of the best experts on this subject based on the ideXlab platform.
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a tandem coupling Smiles Rearrangement cyclization approach to 1 4 benzooxazinones or 1 4 pyridooxazinones under mild conditions
RSC Advances, 2012Co-Authors: Chunjing Zhan, Jiong Jia, Bingchuan Yang, Aiping Huang, Yanli LiuAbstract:A facile and efficient approach to 1,4-benzooxazinone or 1,4-pyridooxazinone scaffolds is developed via Smiles Rearrangement tandem reaction. 1,4-Benzooxazinones or 1,4-pyridooxazinones with diversity at two substituents on their scaffolds were synthesized conveniently in the presence of cesium carbonate at room temperature in good to excellent yields. The reaction mechanism is assumed by a tandem coupling/Smiles Rearrangement/cyclization process.
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One-Pot Synthesis of Fused Pyridazino[4,5-b][1,4]oxazepine-diones via Smiles Rearrangement.
ChemInform, 2012Co-Authors: Yanli Liu, Chunjing Zhan, Aiping HuangAbstract:A convenient synthesis of title compounds (III) from salicyclamides and dichloropyridazinone (II) is achieved by a one-pot coupling/Smiles Rearrangement/cyclization.
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One-Pot Synthesis of Fused Pyridazino[4,5-b][1,4]oxazepine-diones via Smiles Rearrangement
Synlett, 2012Co-Authors: Yanli Liu, Chunjing Zhan, Aiping HuangAbstract:Fused pyridazino[4,5-b][1,4]oxazepine-diones were easily obtained in moderate to excellent yields via Smiles Rearrangement. The synthetic approach is supported by a one-pot couplingSmiles Rearrangement-cyclization process. This process has potential applications in the synthesis of biologically and medicinally relevant compounds.
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A tandem coupling/Smiles Rearrangement/ cyclization approach to 1,4-benzooxazinones or 1,4-pyridooxazinones under mild conditions
RSC Advances, 2012Co-Authors: Chunjing Zhan, Jiong Jia, Bingchuan Yang, Aiping Huang, Yanli LiuAbstract:A facile and efficient approach to 1,4-benzooxazinone or 1,4-pyridooxazinone scaffolds is developed via Smiles Rearrangement tandem reaction. 1,4-Benzooxazinones or 1,4-pyridooxazinones with diversity at two substituents on their scaffolds were synthesized conveniently in the presence of cesium carbonate at room temperature in good to excellent yields. The reaction mechanism is assumed by a tandem coupling/Smiles Rearrangement/cyclization process.
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Regioselective synthesis of fused oxazepinone scaffolds through one-pot Smiles Rearrangement tandem reaction.
ACS combinatorial science, 2011Co-Authors: Yanli Liu, Aiping Huang, Chunxiao Chu, Chunjing ZhanAbstract:The paper describes a convenient and facile methodology for the regioselective synthesis of fused oxazepinone scaffolds. This process is an efficient construction of the oxazepinone scaffold by a one-pot coupling/Smiles Rearrangement/cyclization approach. This transition metal-free process has potential applications in the synthesis of biologically and medicinally relevant compounds.
Tabitha E. Wood - One of the best experts on this subject based on the ideXlab platform.
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The Truce-Smiles Rearrangement and Related Reactions: A Review
Canadian Journal of Chemistry, 2017Co-Authors: Anna R.p. Henderson, Joel R. Kosowan, Tabitha E. WoodAbstract:The Truce–Smiles Rearrangement is an X → C aryl migration reaction that is achieved by an intramolecular nucleophilic aromatic substitution pathway. The reaction exhibits a wide substrate scope with respect to a migrating aryl ring and leaving group, appearing in many different tandem reaction sequences, to achieve a wide variety of product outcomes. We present an extensive survey of reported examples of the Truce–Smiles Rearrangement from the chemistry literature (1950s until present) organized by various substrate design variables or aspects of the reaction method. Present deficiencies in our understanding of the reaction are identified with recommendations for future research directions and useful developments in the application of the reaction are celebrated.
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Truce–Smiles Rearrangement of substituted phenyl ethers
Organic & biomolecular chemistry, 2015Co-Authors: Joel R. Kosowan, Zemane W'giorgis, Ravneet Grewal, Tabitha E. WoodAbstract:The requirement of aryl ring activation by strong-electron withdrawing substituents in substrates for the intramolecular nucleophilic aromatic substitution reaction known as the Truce–Smiles Rearrangement was examined. Preliminary mechanistic experiments support the SNAr mechanism, including 1H and 13C NMR spectra of a Meisenheimer intermediate formed in situ. The Rearrangement was generally observed to be successful for substrates with strong electron withdrawing substituents, such as nitro-, cyano-, and benzoyl- functional groups, but also for those with multiple, weakly electron withdrawing substituents, such as chloro- and bromo-functional groups. These results lend further clarification to the effect of aryl substituents in this type of SNAr reaction. Additionally, the survey revealed several tandem cyclization and/or elimination reactions accessed by certain substrates.
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truce Smiles Rearrangement of substituted phenyl ethers
Organic and Biomolecular Chemistry, 2015Co-Authors: Joel R. Kosowan, Ravneet Grewal, Zemane Wgiorgis, Tabitha E. WoodAbstract:The requirement of aryl ring activation by strong-electron withdrawing substituents in substrates for the intramolecular nucleophilic aromatic substitution reaction known as the Truce–Smiles Rearrangement was examined. Preliminary mechanistic experiments support the SNAr mechanism, including 1H and 13C NMR spectra of a Meisenheimer intermediate formed in situ. The Rearrangement was generally observed to be successful for substrates with strong electron withdrawing substituents, such as nitro-, cyano-, and benzoyl- functional groups, but also for those with multiple, weakly electron withdrawing substituents, such as chloro- and bromo-functional groups. These results lend further clarification to the effect of aryl substituents in this type of SNAr reaction. Additionally, the survey revealed several tandem cyclization and/or elimination reactions accessed by certain substrates.