Substrate Controlled [3+3] Relay Catalytic Cyclization of α-(3-Isoindolinonyl) Propargylic Alcohols with 5-Aminoisoxazoles
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作者:
Li, Wenzhe
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Chinese Acad Sci, Chengdu Inst Organ Chem, Asymmetr Synth & Chiraltechnol Key Lab Sichuan Pro, Chengdu, Peoples R China
Univ Chinese Acad Sci, Beijing, Peoples R ChinaChinese Acad Sci, Chengdu Inst Organ Chem, Asymmetr Synth & Chiraltechnol Key Lab Sichuan Pro, Chengdu, Peoples R China
Li, Wenzhe
[1
,3
]
Gao, Min
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Xihua Univ, Dept Chem, Chengdu, Peoples R ChinaChinese Acad Sci, Chengdu Inst Organ Chem, Asymmetr Synth & Chiraltechnol Key Lab Sichuan Pro, Chengdu, Peoples R China
Gao, Min
[2
]
Li, Min
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Chinese Acad Sci, Chengdu Inst Organ Chem, Asymmetr Synth & Chiraltechnol Key Lab Sichuan Pro, Chengdu, Peoples R China
Univ Chinese Acad Sci, Beijing, Peoples R ChinaChinese Acad Sci, Chengdu Inst Organ Chem, Asymmetr Synth & Chiraltechnol Key Lab Sichuan Pro, Chengdu, Peoples R China
Li, Min
[1
,3
]
Yang, Shuang
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Xihua Univ, Dept Chem, Chengdu, Peoples R ChinaChinese Acad Sci, Chengdu Inst Organ Chem, Asymmetr Synth & Chiraltechnol Key Lab Sichuan Pro, Chengdu, Peoples R China
Yang, Shuang
[2
]
Zhang, Xiaomei
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Chinese Acad Sci, Chengdu Inst Organ Chem, Asymmetr Synth & Chiraltechnol Key Lab Sichuan Pro, Chengdu, Peoples R China
Xihua Univ, Dept Chem, Chengdu, Peoples R China
Univ Chinese Acad Sci, Beijing, Peoples R ChinaChinese Acad Sci, Chengdu Inst Organ Chem, Asymmetr Synth & Chiraltechnol Key Lab Sichuan Pro, Chengdu, Peoples R China
Zhang, Xiaomei
[1
,2
,3
]
机构:
[1] Chinese Acad Sci, Chengdu Inst Organ Chem, Asymmetr Synth & Chiraltechnol Key Lab Sichuan Pro, Chengdu, Peoples R China
[2] Xihua Univ, Dept Chem, Chengdu, Peoples R China
[3] Univ Chinese Acad Sci, Beijing, Peoples R China
Two different skeletons have been constructed by cyclization of alpha-(3-isoindolinonyl) propargylic alcohols with 5-aminoisoxazoles bearing different N-substituents under the relay catalysis of Bronsted acid and Lewis acid. This method provided spiro-isoindolinone-dihydropyridines with moderate to high yields (up to 99 %) as well as isoxazolo[4,5-b]pyridines in moderate to good yields (up to 86 %). The structures of two products were determined by X-ray crystal structural analyses. Moreover, fluorescence testing proved that one of the isoxazolo[4,5-b]pyridines exhibited aggregation induced emission (AIE) effect. Finally, the control experiments revealed the possible reaction mechanism. Relay catalytic [3+3] cyclization of alpha-(3-isoindolinonyl) propargylic alcohols with 5-aminoisoxazoles bearing different N-substituents provide novel spiro-isoindolinone-dihydropyridines as well as isoxazolo[4,5-b]pyridines in moderate to good yields. The structures of two products are determined by X-ray crystal structural analyses. image
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Alma Mater Studiorum Univ Bologna, Dept Chem G Ciamician, Via Selmi 2, I-40126 Bologna, ItalyAlma Mater Studiorum Univ Bologna, Dept Chem G Ciamician, Via Selmi 2, I-40126 Bologna, Italy
Manoni, Elisabetta
Daka, Mario
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Alma Mater Studiorum Univ Bologna, Dept Chem G Ciamician, Via Selmi 2, I-40126 Bologna, ItalyAlma Mater Studiorum Univ Bologna, Dept Chem G Ciamician, Via Selmi 2, I-40126 Bologna, Italy
Daka, Mario
Mastandrea, Marco M.
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Alma Mater Studiorum Univ Bologna, Dept Chem G Ciamician, Via Selmi 2, I-40126 Bologna, ItalyAlma Mater Studiorum Univ Bologna, Dept Chem G Ciamician, Via Selmi 2, I-40126 Bologna, Italy
Mastandrea, Marco M.
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Nisi, Assunta De
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Monari, Magda
Bandini, Marco
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Alma Mater Studiorum Univ Bologna, Dept Chem G Ciamician, Via Selmi 2, I-40126 Bologna, ItalyAlma Mater Studiorum Univ Bologna, Dept Chem G Ciamician, Via Selmi 2, I-40126 Bologna, Italy