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Shun-yi Wang - One of the best experts on this subject based on the ideXlab platform.
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Cascade Trisulfur Radical Anion (S3•-) Addition/Electron Detosylation Process for the Synthesis of 1,2,3-Thiadiazoles and Isothiazoles.
The Journal of organic chemistry, 2018Co-Authors: Bei-bei Liu, Hui-wen Bai, Huan Liu, Shun-yi WangAbstract:Trisulfur radical anion (S3•–) mediated reactions with in situ formed azoalkenes and α,β-usaturated N-sulfonylimines for the construction of 1,2,3-thiadiazoles and isothiazoles has been developed. S3•– is in situ generated from potassium sulfide in DMF. These two approaches provide a new, safe, and simple way to construct 4-subsituted 1,2,3-thiadiazoles, 5-subsituted 1,2,3-thiadiazoles, and isothiazole in good yields. The reactions include the formation of the new C–S and N–S bonds via S3•– addition and electron Detosylation under mild conditions.
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cascade trisulfur radical anion s3 addition electron Detosylation process for the synthesis of 1 2 3 thiadiazoles and isothiazoles
Journal of Organic Chemistry, 2018Co-Authors: Bei-bei Liu, Hui-wen Bai, Huan Liu, Shun-yi WangAbstract:Trisulfur radical anion (S3•–) mediated reactions with in situ formed azoalkenes and α,β-usaturated N-sulfonylimines for the construction of 1,2,3-thiadiazoles and isothiazoles has been developed. S3•– is in situ generated from potassium sulfide in DMF. These two approaches provide a new, safe, and simple way to construct 4-subsituted 1,2,3-thiadiazoles, 5-subsituted 1,2,3-thiadiazoles, and isothiazole in good yields. The reactions include the formation of the new C–S and N–S bonds via S3•– addition and electron Detosylation under mild conditions.
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Cascade Trisulfur Radical Anion (S3•–) Addition/Electron Detosylation Process for the Synthesis of 1,2,3-Thiadiazoles and Isothiazoles
2018Co-Authors: Bei-bei Liu, Hui-wen Bai, Huan Liu, Shun-yi WangAbstract:Trisulfur radical anion (S3•–) mediated reactions with in situ formed azoalkenes and α,β-usaturated N-sulfonylimines for the construction of 1,2,3-thiadiazoles and isothiazoles has been developed. S3•– is in situ generated from potassium sulfide in DMF. These two approaches provide a new, safe, and simple way to construct 4-subsituted 1,2,3-thiadiazoles, 5-subsituted 1,2,3-thiadiazoles, and isothiazole in good yields. The reactions include the formation of the new C–S and N–S bonds via S3•– addition and electron Detosylation under mild conditions
Bei-bei Liu - One of the best experts on this subject based on the ideXlab platform.
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Cascade Trisulfur Radical Anion (S3•-) Addition/Electron Detosylation Process for the Synthesis of 1,2,3-Thiadiazoles and Isothiazoles.
The Journal of organic chemistry, 2018Co-Authors: Bei-bei Liu, Hui-wen Bai, Huan Liu, Shun-yi WangAbstract:Trisulfur radical anion (S3•–) mediated reactions with in situ formed azoalkenes and α,β-usaturated N-sulfonylimines for the construction of 1,2,3-thiadiazoles and isothiazoles has been developed. S3•– is in situ generated from potassium sulfide in DMF. These two approaches provide a new, safe, and simple way to construct 4-subsituted 1,2,3-thiadiazoles, 5-subsituted 1,2,3-thiadiazoles, and isothiazole in good yields. The reactions include the formation of the new C–S and N–S bonds via S3•– addition and electron Detosylation under mild conditions.
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cascade trisulfur radical anion s3 addition electron Detosylation process for the synthesis of 1 2 3 thiadiazoles and isothiazoles
Journal of Organic Chemistry, 2018Co-Authors: Bei-bei Liu, Hui-wen Bai, Huan Liu, Shun-yi WangAbstract:Trisulfur radical anion (S3•–) mediated reactions with in situ formed azoalkenes and α,β-usaturated N-sulfonylimines for the construction of 1,2,3-thiadiazoles and isothiazoles has been developed. S3•– is in situ generated from potassium sulfide in DMF. These two approaches provide a new, safe, and simple way to construct 4-subsituted 1,2,3-thiadiazoles, 5-subsituted 1,2,3-thiadiazoles, and isothiazole in good yields. The reactions include the formation of the new C–S and N–S bonds via S3•– addition and electron Detosylation under mild conditions.
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Cascade Trisulfur Radical Anion (S3•–) Addition/Electron Detosylation Process for the Synthesis of 1,2,3-Thiadiazoles and Isothiazoles
2018Co-Authors: Bei-bei Liu, Hui-wen Bai, Huan Liu, Shun-yi WangAbstract:Trisulfur radical anion (S3•–) mediated reactions with in situ formed azoalkenes and α,β-usaturated N-sulfonylimines for the construction of 1,2,3-thiadiazoles and isothiazoles has been developed. S3•– is in situ generated from potassium sulfide in DMF. These two approaches provide a new, safe, and simple way to construct 4-subsituted 1,2,3-thiadiazoles, 5-subsituted 1,2,3-thiadiazoles, and isothiazole in good yields. The reactions include the formation of the new C–S and N–S bonds via S3•– addition and electron Detosylation under mild conditions
Manas K. Ghorai - One of the best experts on this subject based on the ideXlab platform.
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Stereoselective Construction of Pyrazinoindoles and Oxazinoindoles via Ring-Opening/Pictet-Spengler Reaction of Aziridines and Epoxides with 3-Methylindoles and Carbonyls.
The Journal of organic chemistry, 2018Co-Authors: Imtiyaz Ahmad Wani, Subhomoy Das, Shobhan Mondal, Manas K. GhoraiAbstract:A highly efficient and stereoselective route to access 1,3-disubstituted 1,2,3,4-tetrahydropyrazino[1,2-a]indoles and 3,4-dihydro-1H-[1,4]oxazino[4,3-a]indoles with excellent stereoselectivity (de, ee >99%) via base mediated ring opening of aziridines/epoxides with 3-methylindoles followed by BF3·OEt2 catalyzed Pictet-Spengler reaction is accomplished. Interestingly, PTSA promoted cyclization led to the formation of oxidized 3,4-dihydropyrazino[1,2-a]indoles in excellent yields via an unprecedented Pictet-Spengler-Detosylation cascade.
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Stereoselective Construction of Pyrazinoindoles and Oxazinoindoles via Ring-Opening/Pictet-Spengler Reaction of Aziridines and Epoxides with 3‑Methylindoles and Carbonyls
2018Co-Authors: Imtiyaz Ahmad Wani, Shobhan Mondal, Subhomoy Das, Manas K. GhoraiAbstract:A highly efficient and stereoselective route to access 1,3-disubstituted 1,2,3,4-tetrahydropyrazino[1,2-a]indoles and 3,4-dihydro-1H-[1,4]oxazino[4,3-a]indoles with excellent stereoselectivity (de, ee >99%) via base mediated ring opening of aziridines/epoxides with 3-methylindoles followed by BF3·OEt2 catalyzed Pictet-Spengler reaction is accomplished. Interestingly, PTSA promoted cyclization led to the formation of oxidized 3,4-dihydropyrazino[1,2-a]indoles in excellent yields via an unprecedented Pictet-Spengler-Detosylation cascade
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accessing quinoxalines by ring opening cyclization Detosylation aromatization of activated aziridines with 2 bromoanilines synthesis of tyrphostin ag 1296
European Journal of Organic Chemistry, 2017Co-Authors: Chandan Kumar Shahi, Sajan Pradhan, Aditya Bhattacharyya, Raushan Kumar, Manas K. GhoraiAbstract:Synthesis of substituted 2-arylquinoxalines via an unprecedented Cu(I) catalyzed ring-opening-cyclization followed by Detosylation-aromatization of activated aziridines with 2-bromoanilines has been accomplished. The transformation efficiently accommodates a wide range of aziridines and 2-bromoanilines to afford the desired quinoxaline frameworks in excellent yields (up to 86%) as a single regioisomer. The methodology has also been conveniently applied for the synthesis of tyrphostin AG 1296, a PDGF-receptor tyrosine kinase inhibitor.
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Accessing Quinoxalines by Ring‐Opening/Cyclization/Detosylation/Aromatization of Activated Aziridines with 2‐Bromoanilines: Synthesis of Tyrphostin AG 1296
European Journal of Organic Chemistry, 2017Co-Authors: Chandan Kumar Shahi, Sajan Pradhan, Aditya Bhattacharyya, Raushan Kumar, Manas K. GhoraiAbstract:Synthesis of substituted 2-arylquinoxalines via an unprecedented Cu(I) catalyzed ring-opening-cyclization followed by Detosylation-aromatization of activated aziridines with 2-bromoanilines has been accomplished. The transformation efficiently accommodates a wide range of aziridines and 2-bromoanilines to afford the desired quinoxaline frameworks in excellent yields (up to 86%) as a single regioisomer. The methodology has also been conveniently applied for the synthesis of tyrphostin AG 1296, a PDGF-receptor tyrosine kinase inhibitor.
Mitsuhiro Yoshimatsu - One of the best experts on this subject based on the ideXlab platform.
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ni pd catalyzed cyclization of sulfanyl 1 6 diynes synthesis of 1 homonucleoside analogues
Journal of Organic Chemistry, 2017Co-Authors: Yuka Kobayashi, Rena Tanahashi, Yui Yamaguchi, Noriyuki Hatae, Masanori Kobayashi, Yoshihito Ueno, Mitsuhiro YoshimatsuAbstract:The Ni–Pd catalyzed addition–cyclization of sulfanyl 1,6-diynes 2–9 with nucleobases is described. The reactions of N-tethered 1,6-diynes with N3-benzoylthymine, N4,N4-bis(Boc)cytosine, N3-benzoyluracil and N6,N6-bis(Boc)adenine exclusively afforded the pyrrolylmethyl and furylmethyl nucleotides in good yields. Deprotection of nucleobases was completed by treatment with acids or bases. Furthermore, the reactions of pyrroles and furans with nucleophiles such as alkoxides and amines underwent Detosylation and conversion to the alkoxymethyl- and arylaminomethyl-pyrroles and furans in good yields.
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Ni–Pd Catalyzed Cyclization of Sulfanyl 1,6-Diynes: Synthesis of 1′-Homonucleoside Analogues
Journal of Organic Chemistry, 2017Co-Authors: Yuka Kobayashi, Rena Tanahashi, Yui Yamaguchi, Noriyuki Hatae, Masanori Kobayashi, Yoshihito Ueno, Mitsuhiro YoshimatsuAbstract:The Ni–Pd catalyzed addition–cyclization of sulfanyl 1,6-diynes 2–9 with nucleobases is described. The reactions of N-tethered 1,6-diynes with N3-benzoylthymine, N4,N4-bis(Boc)cytosine, N3-benzoyluracil and N6,N6-bis(Boc)adenine exclusively afforded the pyrrolylmethyl and furylmethyl nucleotides in good yields. Deprotection of nucleobases was completed by treatment with acids or bases. Furthermore, the reactions of pyrroles and furans with nucleophiles such as alkoxides and amines underwent Detosylation and conversion to the alkoxymethyl- and arylaminomethyl-pyrroles and furans in good yields.
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Ni–Pd Catalyzed Cyclization of Sulfanyl 1,6-Diynes: Synthesis of 1′‑Homonucleoside Analogues
2017Co-Authors: Yuka Kobayashi, Rena Tanahashi, Yui Yamaguchi, Noriyuki Hatae, Masanori Kobayashi, Yoshihito Ueno, Mitsuhiro YoshimatsuAbstract:The Ni–Pd catalyzed addition–cyclization of sulfanyl 1,6-diynes 2–9 with nucleobases is described. The reactions of N-tethered 1,6-diynes with N3-benzoylthymine, N4,N4-bis(Boc)cytosine, N3-benzoyluracil and N6,N6-bis(Boc)adenine exclusively afforded the pyrrolylmethyl and furylmethyl nucleotides in good yields. Deprotection of nucleobases was completed by treatment with acids or bases. Furthermore, the reactions of pyrroles and furans with nucleophiles such as alkoxides and amines underwent Detosylation and conversion to the alkoxymethyl- and arylaminomethyl-pyrroles and furans in good yields
Huan Liu - One of the best experts on this subject based on the ideXlab platform.
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Cascade Trisulfur Radical Anion (S3•-) Addition/Electron Detosylation Process for the Synthesis of 1,2,3-Thiadiazoles and Isothiazoles.
The Journal of organic chemistry, 2018Co-Authors: Bei-bei Liu, Hui-wen Bai, Huan Liu, Shun-yi WangAbstract:Trisulfur radical anion (S3•–) mediated reactions with in situ formed azoalkenes and α,β-usaturated N-sulfonylimines for the construction of 1,2,3-thiadiazoles and isothiazoles has been developed. S3•– is in situ generated from potassium sulfide in DMF. These two approaches provide a new, safe, and simple way to construct 4-subsituted 1,2,3-thiadiazoles, 5-subsituted 1,2,3-thiadiazoles, and isothiazole in good yields. The reactions include the formation of the new C–S and N–S bonds via S3•– addition and electron Detosylation under mild conditions.
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cascade trisulfur radical anion s3 addition electron Detosylation process for the synthesis of 1 2 3 thiadiazoles and isothiazoles
Journal of Organic Chemistry, 2018Co-Authors: Bei-bei Liu, Hui-wen Bai, Huan Liu, Shun-yi WangAbstract:Trisulfur radical anion (S3•–) mediated reactions with in situ formed azoalkenes and α,β-usaturated N-sulfonylimines for the construction of 1,2,3-thiadiazoles and isothiazoles has been developed. S3•– is in situ generated from potassium sulfide in DMF. These two approaches provide a new, safe, and simple way to construct 4-subsituted 1,2,3-thiadiazoles, 5-subsituted 1,2,3-thiadiazoles, and isothiazole in good yields. The reactions include the formation of the new C–S and N–S bonds via S3•– addition and electron Detosylation under mild conditions.
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Cascade Trisulfur Radical Anion (S3•–) Addition/Electron Detosylation Process for the Synthesis of 1,2,3-Thiadiazoles and Isothiazoles
2018Co-Authors: Bei-bei Liu, Hui-wen Bai, Huan Liu, Shun-yi WangAbstract:Trisulfur radical anion (S3•–) mediated reactions with in situ formed azoalkenes and α,β-usaturated N-sulfonylimines for the construction of 1,2,3-thiadiazoles and isothiazoles has been developed. S3•– is in situ generated from potassium sulfide in DMF. These two approaches provide a new, safe, and simple way to construct 4-subsituted 1,2,3-thiadiazoles, 5-subsituted 1,2,3-thiadiazoles, and isothiazole in good yields. The reactions include the formation of the new C–S and N–S bonds via S3•– addition and electron Detosylation under mild conditions