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Anxin Wu - One of the best experts on this subject based on the ideXlab platform.
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C(sp3)–H Bond Functionalization of Benzo[c]Oxepines via C–O bond Cleavage: Formal [3+3] Synthesis of Multisubstituted Chromans
Journal of Organic Chemistry, 2018Co-Authors: Miao Wang, Jiachen Xiang, Bocheng Tang, Yan Cheng, Zixuan Wang, Yandong Wu, Jin-tian Ma, Anxin WuAbstract:An efficient base-promoted C(sp3)–H bond functionalization strategy for the synthesis of multisubstituted chromans from the formal [3+3] cycloaddition of benzo[c]Oxepines and electron-rich phenols has been developed. The corresponding 4H-chromenes can be easily obtained in excellent yields by simple filtration from chromans. Preliminary mechanistic studies indicate that the C–O bond cleavage is the key step for the C(sp3)–H bond functionalization and that this reaction could have occurred through tandem C–O bond cleavage/Michael addition/annulation reactions.
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c sp3 h bond functionalization of benzo c Oxepines via c o bond cleavage formal 3 3 synthesis of multisubstituted chromans
Journal of Organic Chemistry, 2018Co-Authors: Miao Wang, Jiachen Xiang, Bocheng Tang, Yan Cheng, Zixuan Wang, Yandong Wu, Anxin WuAbstract:An efficient base-promoted C(sp3)–H bond functionalization strategy for the synthesis of multisubstituted chromans from the formal [3+3] cycloaddition of benzo[c]Oxepines and electron-rich phenols has been developed. The corresponding 4H-chromenes can be easily obtained in excellent yields by simple filtration from chromans. Preliminary mechanistic studies indicate that the C–O bond cleavage is the key step for the C(sp3)–H bond functionalization and that this reaction could have occurred through tandem C–O bond cleavage/Michael addition/annulation reactions.
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generation of o quinodimethanes o qdms from benzo c Oxepines and the synthetic application for polysubstituted tetrahydronaphthalenes
Tetrahedron, 2015Co-Authors: Jungang Wang, Jiachen Xiang, Miao Wang, Hailing Xi, Anxin WuAbstract:Abstract A novel method for the generation of o -quinodimethane ( o -QDM) intermediates is reported using a mild and efficient base-promoted ring-opening of benzo[ c ]Oxepines. Among the benzo[ c ]Oxepines studied, indanone containing analogues demonstrated the greatest variety of reactivity. A number of decay modes were observed, in addition with trapping of the o -QDM intermediates using dienophiles for the synthesis of polysubstituted tetrahydronaphthalenes with high regioselectivity. This research provided a novel method to generate o -QDM intermediates from benzo[ c ]oxepine precursors.
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synthesis of substituted naphthalenes from α substituted ketones and 1 2 bis halomethyl benzenes including a rearrangement aromatization of benzo c oxepine
Tetrahedron, 2014Co-Authors: Jungang Wang, Jiachen Xiang, Miao Wang, Jie Guan, Anxin WuAbstract:Abstract An efficient and practical method for the synthesis of cyano, sulfonyl and phosphoryl substituted naphthalene derivatives via the rearrangement aromatization of benzo[c]oxepine has been developed. The system holds the advantages of metal catalysts free, and mild reaction conditions.
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direct synthesis of substituted naphthalenes from 1 3 dicarbonyl compounds and 1 2 bis halomethyl benzenes including a novel rearrangement aromatization of benzo c oxepine
ChemInform, 2013Co-Authors: Jungang Wang, Jiachen Xiang, Meng Wang, Anxin WuAbstract:Substituted naphthalene derivatives are obtained by rearrangement aromatization of benzo[c]Oxepines (I).
Peter Langer - One of the best experts on this subject based on the ideXlab platform.
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One-Pot Synthesis of Dibenzo[b,d]Oxepines via Olefinic C–F Bond Functionalization and Intramolecular Pd-Catalyzed C–H Arylation
Journal of Organic Chemistry, 2018Co-Authors: Elina Ausekle, Peter Ehlers, Alexander Villinger, Peter LangerAbstract:We report base-mediated reactions of 1-bromo-2-(2,2-difluorovinyl)benzenes with phenols followed by Pd-catalyzed intramolecular C–H arylation, which offers a novel route to a pharmaceutically relevant class of compounds, Oxepines. Construction of these medium-sized ring structures proceeds as a one-pot two-step reaction through diaryl ketene acetals as intermediates. It allows to obtain various dibenz[b,d]oxepine derivatives in moderate to high yields.
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one pot synthesis of dibenzo b d Oxepines via olefinic c f bond functionalization and intramolecular pd catalyzed c h arylation
Journal of Organic Chemistry, 2018Co-Authors: Elina Ausekle, Peter Ehlers, Alexander Villinger, Peter LangerAbstract:We report base-mediated reactions of 1-bromo-2-(2,2-difluorovinyl)benzenes with phenols followed by Pd-catalyzed intramolecular C–H arylation, which offers a novel route to a pharmaceutically relevant class of compounds, Oxepines. Construction of these medium-sized ring structures proceeds as a one-pot two-step reaction through diaryl ketene acetals as intermediates. It allows to obtain various dibenz[b,d]oxepine derivatives in moderate to high yields.
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synthesis of 2 5 dihydrobenzo b Oxepines and 5 6 dihydro 2h benzo b oxocines based on a 3 3 cyclization olefin metathesis strategy
Tetrahedron Letters, 2006Co-Authors: Van Thi Hong Nguyen, Esen Bellur, Peter LangerAbstract:Abstract Functionalized 2,5-dihydrobenzo[ b ]Oxepines and 5,6-dihydro-2 H -benzo[ b ]oxocines were prepared based on a ‘[3+3] cyclization-olefin-metathesis’ strategy.
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Synthesis of 2,5-dihydrobenzo[b]Oxepines and 5,6-dihydro-2H-benzo[b]oxocines based on a ‘[3+3] cyclization-olefin-metathesis’ strategy
Tetrahedron Letters, 2006Co-Authors: Van Thi Hong Nguyen, Esen Bellur, Peter LangerAbstract:Abstract Functionalized 2,5-dihydrobenzo[ b ]Oxepines and 5,6-dihydro-2 H -benzo[ b ]oxocines were prepared based on a ‘[3+3] cyclization-olefin-metathesis’ strategy.
Jiachen Xiang - One of the best experts on this subject based on the ideXlab platform.
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C(sp3)–H Bond Functionalization of Benzo[c]Oxepines via C–O bond Cleavage: Formal [3+3] Synthesis of Multisubstituted Chromans
Journal of Organic Chemistry, 2018Co-Authors: Miao Wang, Jiachen Xiang, Bocheng Tang, Yan Cheng, Zixuan Wang, Yandong Wu, Jin-tian Ma, Anxin WuAbstract:An efficient base-promoted C(sp3)–H bond functionalization strategy for the synthesis of multisubstituted chromans from the formal [3+3] cycloaddition of benzo[c]Oxepines and electron-rich phenols has been developed. The corresponding 4H-chromenes can be easily obtained in excellent yields by simple filtration from chromans. Preliminary mechanistic studies indicate that the C–O bond cleavage is the key step for the C(sp3)–H bond functionalization and that this reaction could have occurred through tandem C–O bond cleavage/Michael addition/annulation reactions.
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c sp3 h bond functionalization of benzo c Oxepines via c o bond cleavage formal 3 3 synthesis of multisubstituted chromans
Journal of Organic Chemistry, 2018Co-Authors: Miao Wang, Jiachen Xiang, Bocheng Tang, Yan Cheng, Zixuan Wang, Yandong Wu, Anxin WuAbstract:An efficient base-promoted C(sp3)–H bond functionalization strategy for the synthesis of multisubstituted chromans from the formal [3+3] cycloaddition of benzo[c]Oxepines and electron-rich phenols has been developed. The corresponding 4H-chromenes can be easily obtained in excellent yields by simple filtration from chromans. Preliminary mechanistic studies indicate that the C–O bond cleavage is the key step for the C(sp3)–H bond functionalization and that this reaction could have occurred through tandem C–O bond cleavage/Michael addition/annulation reactions.
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generation of o quinodimethanes o qdms from benzo c Oxepines and the synthetic application for polysubstituted tetrahydronaphthalenes
Tetrahedron, 2015Co-Authors: Jungang Wang, Jiachen Xiang, Miao Wang, Hailing Xi, Anxin WuAbstract:Abstract A novel method for the generation of o -quinodimethane ( o -QDM) intermediates is reported using a mild and efficient base-promoted ring-opening of benzo[ c ]Oxepines. Among the benzo[ c ]Oxepines studied, indanone containing analogues demonstrated the greatest variety of reactivity. A number of decay modes were observed, in addition with trapping of the o -QDM intermediates using dienophiles for the synthesis of polysubstituted tetrahydronaphthalenes with high regioselectivity. This research provided a novel method to generate o -QDM intermediates from benzo[ c ]oxepine precursors.
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synthesis of substituted naphthalenes from α substituted ketones and 1 2 bis halomethyl benzenes including a rearrangement aromatization of benzo c oxepine
Tetrahedron, 2014Co-Authors: Jungang Wang, Jiachen Xiang, Miao Wang, Jie Guan, Anxin WuAbstract:Abstract An efficient and practical method for the synthesis of cyano, sulfonyl and phosphoryl substituted naphthalene derivatives via the rearrangement aromatization of benzo[c]oxepine has been developed. The system holds the advantages of metal catalysts free, and mild reaction conditions.
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direct synthesis of substituted naphthalenes from 1 3 dicarbonyl compounds and 1 2 bis halomethyl benzenes including a novel rearrangement aromatization of benzo c oxepine
ChemInform, 2013Co-Authors: Jungang Wang, Jiachen Xiang, Meng Wang, Anxin WuAbstract:Substituted naphthalene derivatives are obtained by rearrangement aromatization of benzo[c]Oxepines (I).
Miao Wang - One of the best experts on this subject based on the ideXlab platform.
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C(sp3)–H Bond Functionalization of Benzo[c]Oxepines via C–O bond Cleavage: Formal [3+3] Synthesis of Multisubstituted Chromans
Journal of Organic Chemistry, 2018Co-Authors: Miao Wang, Jiachen Xiang, Bocheng Tang, Yan Cheng, Zixuan Wang, Yandong Wu, Jin-tian Ma, Anxin WuAbstract:An efficient base-promoted C(sp3)–H bond functionalization strategy for the synthesis of multisubstituted chromans from the formal [3+3] cycloaddition of benzo[c]Oxepines and electron-rich phenols has been developed. The corresponding 4H-chromenes can be easily obtained in excellent yields by simple filtration from chromans. Preliminary mechanistic studies indicate that the C–O bond cleavage is the key step for the C(sp3)–H bond functionalization and that this reaction could have occurred through tandem C–O bond cleavage/Michael addition/annulation reactions.
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c sp3 h bond functionalization of benzo c Oxepines via c o bond cleavage formal 3 3 synthesis of multisubstituted chromans
Journal of Organic Chemistry, 2018Co-Authors: Miao Wang, Jiachen Xiang, Bocheng Tang, Yan Cheng, Zixuan Wang, Yandong Wu, Anxin WuAbstract:An efficient base-promoted C(sp3)–H bond functionalization strategy for the synthesis of multisubstituted chromans from the formal [3+3] cycloaddition of benzo[c]Oxepines and electron-rich phenols has been developed. The corresponding 4H-chromenes can be easily obtained in excellent yields by simple filtration from chromans. Preliminary mechanistic studies indicate that the C–O bond cleavage is the key step for the C(sp3)–H bond functionalization and that this reaction could have occurred through tandem C–O bond cleavage/Michael addition/annulation reactions.
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generation of o quinodimethanes o qdms from benzo c Oxepines and the synthetic application for polysubstituted tetrahydronaphthalenes
Tetrahedron, 2015Co-Authors: Jungang Wang, Jiachen Xiang, Miao Wang, Hailing Xi, Anxin WuAbstract:Abstract A novel method for the generation of o -quinodimethane ( o -QDM) intermediates is reported using a mild and efficient base-promoted ring-opening of benzo[ c ]Oxepines. Among the benzo[ c ]Oxepines studied, indanone containing analogues demonstrated the greatest variety of reactivity. A number of decay modes were observed, in addition with trapping of the o -QDM intermediates using dienophiles for the synthesis of polysubstituted tetrahydronaphthalenes with high regioselectivity. This research provided a novel method to generate o -QDM intermediates from benzo[ c ]oxepine precursors.
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synthesis of substituted naphthalenes from α substituted ketones and 1 2 bis halomethyl benzenes including a rearrangement aromatization of benzo c oxepine
Tetrahedron, 2014Co-Authors: Jungang Wang, Jiachen Xiang, Miao Wang, Jie Guan, Anxin WuAbstract:Abstract An efficient and practical method for the synthesis of cyano, sulfonyl and phosphoryl substituted naphthalene derivatives via the rearrangement aromatization of benzo[c]oxepine has been developed. The system holds the advantages of metal catalysts free, and mild reaction conditions.
Rama Krishna Kancha - One of the best experts on this subject based on the ideXlab platform.
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fecl3 catalysed 7 membered ring formation in a single pot a new route to indole fused Oxepines azepines and their cytotoxic activity
Organic and Biomolecular Chemistry, 2017Co-Authors: Shiva K Kumar, Meesa Siddi Ramulu, Bandari Rajesham, Praveen N Kumar, Vani Voora, Rama Krishna KanchaAbstract:Various oxepine and azepine fused N-heterocyclic derivatives were synthesized using a new and one-pot reaction of 2,3-dichloro quinoxaline/pyrazine with 2-(1H-indol-2-yl)phenol/aniline in the presence of 25 mol% FeCl3. The reaction proceeded via C–C bond followed by C–X (X = O or N) bond formation to construct the central 7-membered ring, affording the desired products in good yields. The structure assignment was confirmed by the single crystal X-ray analysis of a synthesized oxepine fused N-heterocycle derivative. Most of the synthesized compounds were found to be promising when tested for their anti-proliferative properties against cervical and breast cancer cell lines.
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FeCl3 catalysed 7-membered ring formation in a single pot: a new route to indole-fused Oxepines/azepines and their cytotoxic activity
Organic and Biomolecular Chemistry, 2017Co-Authors: K. Shiva Kumar, Meesa Siddi Ramulu, Bandari Rajesham, Vani Voora, N. Praveen Kumar, Rama Krishna KanchaAbstract:Various oxepine and azepine fused N-heterocyclic derivatives were synthesized using a new and one-pot reaction of 2,3-dichloro quinoxaline/pyrazine with 2-(1H-indol-2-yl)phenol/aniline in the presence of 25 mol% FeCl3. The reaction proceeded via C–C bond followed by C–X (X = O or N) bond formation to construct the central 7-membered ring, affording the desired products in good yields. The structure assignment was confirmed by the single crystal X-ray analysis of a synthesized oxepine fused N-heterocycle derivative. Most of the synthesized compounds were found to be promising when tested for their anti-proliferative properties against cervical and breast cancer cell lines.
