The Experts below are selected from a list of 189 Experts worldwide ranked by ideXlab platform
Masahiro Murakami - One of the best experts on this subject based on the ideXlab platform.
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facile synthesis of 2 5 disubstituted thiazoles from terminal alkynes sulfonyl azides and Thionoesters
ChemInform, 2015Co-Authors: Tomoya Miura, Yuuta Funakoshi, Yoshikazu Fujimoto, Junki Nakahashi, Masahiro MurakamiAbstract:Procedures are evaluated for the preparation of various thiazole structures either from triazole precursors (prepared from terminal alkynes and sulfonyl azides) or directly starting with their formation in a one-pot approach.
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facile synthesis of 2 5 disubstituted thiazoles from terminal alkynes sulfonyl azides and Thionoesters
Organic Letters, 2015Co-Authors: Tomoya Miura, Yuuta Funakoshi, Yoshikazu Fujimoto, Junki Nakahashi, Masahiro MurakamiAbstract:A sequential procedure for the synthesis of 2,5-disubstituted thiazoles from terminal alkynes, sulfonyl azides, and Thionoesters is reported. A copper(I)-catalyzed 1,3-dipolar cycloaddition of terminal alkynes with sulfonyl azides affords 1-sulfonyl-1,2,3-triazoles, which then react with Thionoesters in the presence of a rhodium(II) catalyst. The resulting 3-sulfonyl-4-thiazolines subsequently aromatize into the corresponding 2,5-disubstituted thiazoles by elimination of the sulfonyl group.
Alison Thompson - One of the best experts on this subject based on the ideXlab platform.
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Synthesis and reactivity of 2-Thionoester pyrroles: a route to 2-formyl pyrroles
RSC Advances, 2019Co-Authors: Min Joon Kim, Sophie M. Gaube, Michael H. R. Beh, Craig D. Smith, Alison ThompsonAbstract:2-Functionalised pyrroles exhibit considerable synthetic utility. Herein, the synthesis and reactivity of 2-Thionoester (–C(S)OR) pyrroles is reported. 2-Thionoester pyrroles were synthesised using a Knorr-type approach from aliphatic starting materials. 2-Thionoester pyrroles were reduced to the corresponding 2-formyl pyrroles, or the deuterated formyl variant, in one step using RANEY® nickel, thereby removing the need for the much-utilised hydrolysis/decarboxylation/formylation steps that are typically required to convert Knorr-type 2-carboxylate pyrroles into 2-formyl pyrroles. 2-Thionoester pyrroles proved tolerant of typical functional group interconversions for which the parent 2-carboxylate pyrroles have become known.
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Synthesis and Photobiological Activity of Ru(II) Dyads Derived from Pyrrole-2-carboxylate Thionoesters.
Inorganic chemistry, 2017Co-Authors: Deborah A. Smithen, Michael H. R. Beh, T. Stanley Cameron, Huimin Yin, Marc Hetu, Sherri A. Mcfarland, Alison ThompsonAbstract:The synthesis and characterization of a series of heteroleptic ruthenium(II) dyads derived from pyrrole-2-carboxylate Thionoesters are reported. Ligands bearing a conjugated thiocarbonyl group were found to be more reactive toward Ru(II) complexation compared to analogous all-oxygen pyrrole-2-carboxylate esters, and salient features of the resulting complexes were determined using X-ray crystallography, electronic absorption, and NMR spectroscopy. Selected complexes were evaluated for their potential in photobiological applications, whereupon all compounds demonstrated in vitro photodynamic therapy effects in HL-60 and SK-MEL-28 cells, with low nanomolar activities observed, and exhibited some of the largest photocytotoxicity indices to date (>2000). Importantly, the Ru(II) dyads could be activated by relatively soft doses of visible (100 J cm–2, 29 mW cm–2) or red light (100 J cm–2, 34 mW cm–2), which is compatible with therapeutic applications. Some compounds even demonstrated up to five-fold selectivit...
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Synthesis and Photobiological Activity of Ru(II) Dyads Derived from Pyrrole-2-carboxylate Thionoesters
2017Co-Authors: Deborah A. Smithen, Michael H. R. Beh, Huimin Yin, Marc Hetu, Sherri A. Mcfarland, Stanley T. Cameron, Alison ThompsonAbstract:The synthesis and characterization of a series of heteroleptic ruthenium(II) dyads derived from pyrrole-2-carboxylate Thionoesters are reported. Ligands bearing a conjugated thiocarbonyl group were found to be more reactive toward Ru(II) complexation compared to analogous all-oxygen pyrrole-2-carboxylate esters, and salient features of the resulting complexes were determined using X-ray crystallography, electronic absorption, and NMR spectroscopy. Selected complexes were evaluated for their potential in photobiological applications, whereupon all compounds demonstrated in vitro photodynamic therapy effects in HL-60 and SK-MEL-28 cells, with low nanomolar activities observed, and exhibited some of the largest photocytotoxicity indices to date (>2000). Importantly, the Ru(II) dyads could be activated by relatively soft doses of visible (100 J cm–2, 29 mW cm–2) or red light (100 J cm–2, 34 mW cm–2), which is compatible with therapeutic applications. Some compounds even demonstrated up to five-fold selectivity for malignant cells over noncancerous cells. These complexes were also shown to photocleave, and in some cases unwind, DNA in cell-free experiments. Thus, this new class of Ru(II) dyads has the capacity to interact with and damage biological macromolecules in the cell, making them attractive agents for photodynamic therapy
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Thionation reactions of 2-pyrrole carboxylates
RSC Advances, 2016Co-Authors: Brandon R. Groves, Deborah A. Smithen, T. Stanley Cameron, Alison ThompsonAbstract:Reaction of 2-pyrrole carboxylates with Lawesson's reagent at elevated temperatures results in the corresponding Thionoesters, concurrent with the production of a new class of pyrrole annulated with the (1,3,2)-thiazaphospholidine unit. X-ray crystallography was used to identify the pyrrolic thiazaphospholidine, which was found to have unique structural features compared to literature analogues. Addition of BF3·OEt2 to the thionation procedure was found to produce the corresponding F-BODIPY, constituting a four-step reaction in one-pot. The scope and limitations of these reactions involving the promiscuous Lawesson's reagent are discussed herein.
Tomoya Miura - One of the best experts on this subject based on the ideXlab platform.
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facile synthesis of 2 5 disubstituted thiazoles from terminal alkynes sulfonyl azides and Thionoesters
ChemInform, 2015Co-Authors: Tomoya Miura, Yuuta Funakoshi, Yoshikazu Fujimoto, Junki Nakahashi, Masahiro MurakamiAbstract:Procedures are evaluated for the preparation of various thiazole structures either from triazole precursors (prepared from terminal alkynes and sulfonyl azides) or directly starting with their formation in a one-pot approach.
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facile synthesis of 2 5 disubstituted thiazoles from terminal alkynes sulfonyl azides and Thionoesters
Organic Letters, 2015Co-Authors: Tomoya Miura, Yuuta Funakoshi, Yoshikazu Fujimoto, Junki Nakahashi, Masahiro MurakamiAbstract:A sequential procedure for the synthesis of 2,5-disubstituted thiazoles from terminal alkynes, sulfonyl azides, and Thionoesters is reported. A copper(I)-catalyzed 1,3-dipolar cycloaddition of terminal alkynes with sulfonyl azides affords 1-sulfonyl-1,2,3-triazoles, which then react with Thionoesters in the presence of a rhodium(II) catalyst. The resulting 3-sulfonyl-4-thiazolines subsequently aromatize into the corresponding 2,5-disubstituted thiazoles by elimination of the sulfonyl group.
Yuuta Funakoshi - One of the best experts on this subject based on the ideXlab platform.
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facile synthesis of 2 5 disubstituted thiazoles from terminal alkynes sulfonyl azides and Thionoesters
ChemInform, 2015Co-Authors: Tomoya Miura, Yuuta Funakoshi, Yoshikazu Fujimoto, Junki Nakahashi, Masahiro MurakamiAbstract:Procedures are evaluated for the preparation of various thiazole structures either from triazole precursors (prepared from terminal alkynes and sulfonyl azides) or directly starting with their formation in a one-pot approach.
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facile synthesis of 2 5 disubstituted thiazoles from terminal alkynes sulfonyl azides and Thionoesters
Organic Letters, 2015Co-Authors: Tomoya Miura, Yuuta Funakoshi, Yoshikazu Fujimoto, Junki Nakahashi, Masahiro MurakamiAbstract:A sequential procedure for the synthesis of 2,5-disubstituted thiazoles from terminal alkynes, sulfonyl azides, and Thionoesters is reported. A copper(I)-catalyzed 1,3-dipolar cycloaddition of terminal alkynes with sulfonyl azides affords 1-sulfonyl-1,2,3-triazoles, which then react with Thionoesters in the presence of a rhodium(II) catalyst. The resulting 3-sulfonyl-4-thiazolines subsequently aromatize into the corresponding 2,5-disubstituted thiazoles by elimination of the sulfonyl group.
Junki Nakahashi - One of the best experts on this subject based on the ideXlab platform.
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facile synthesis of 2 5 disubstituted thiazoles from terminal alkynes sulfonyl azides and Thionoesters
ChemInform, 2015Co-Authors: Tomoya Miura, Yuuta Funakoshi, Yoshikazu Fujimoto, Junki Nakahashi, Masahiro MurakamiAbstract:Procedures are evaluated for the preparation of various thiazole structures either from triazole precursors (prepared from terminal alkynes and sulfonyl azides) or directly starting with their formation in a one-pot approach.
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facile synthesis of 2 5 disubstituted thiazoles from terminal alkynes sulfonyl azides and Thionoesters
Organic Letters, 2015Co-Authors: Tomoya Miura, Yuuta Funakoshi, Yoshikazu Fujimoto, Junki Nakahashi, Masahiro MurakamiAbstract:A sequential procedure for the synthesis of 2,5-disubstituted thiazoles from terminal alkynes, sulfonyl azides, and Thionoesters is reported. A copper(I)-catalyzed 1,3-dipolar cycloaddition of terminal alkynes with sulfonyl azides affords 1-sulfonyl-1,2,3-triazoles, which then react with Thionoesters in the presence of a rhodium(II) catalyst. The resulting 3-sulfonyl-4-thiazolines subsequently aromatize into the corresponding 2,5-disubstituted thiazoles by elimination of the sulfonyl group.
