N-Iodosuccinimide-Promoted Cascade Oxoazidation of Alkenyl Oximes: Synthesis of Azido Isoxazolines

doi:10.6023/cjoc202304033

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (12): 4220-4226.DOI: 10.6023/cjoc202304033 Previous Articles Next Articles

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N-碘代丁二酰亚胺促进烯基肟的串联氧叠氮化反应: 合成叠氮化异噁唑啉类化合物

刘浩然^a,†, 俞骏豪^a,†, 曹同阳^a, 齐林^a^,^*(), 王力竞^a^,^b^,^*()

a 河北大学化学与材料科学学院河北保定 071002
b 药物化学与分子诊断教育部重点实验室河北省化学生物学重点实验室河北保定 071002

收稿日期:2023-04-25 修回日期:2023-07-17 发布日期:2023-08-16
作者简介:
^†共同第一作者
基金资助:
国家自然科学基金(21702043); 河北省自然科学基金(B2021201035)

N-Iodosuccinimide-Promoted Cascade Oxoazidation of Alkenyl Oximes: Synthesis of Azido Isoxazolines

Haoran Liu^a,†, Junhao Yu^a,†, Tongyang Cao^a, Lin Qi^a,*(), Lijing Wang^a^,^b,*()

a College of Chemistry and Materials Science, Hebei University, Baoding, Hebei 071002
b Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of the Ministry of Education, Key Laboratory of Chemical Biology of Hebei Province, Baoding, Hebei 071002

Received:2023-04-25 Revised:2023-07-17 Published:2023-08-16
Contact: *E-mail: qilin1013@hbu.edu.cn;wanglj@hbu.edu.cn
About author:
^†The authors contributed equally to this work.
Supported by:
National Natural Science Foundation of China(21702043); Hebei Province Natural Science Foundation(B2021201035)

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Abstract

A N-iodosuccinimide (NIS)-promoted cascade oxoazidation of alkenyl oximes with NaN₃ was developed, and a series of azido isoxazoline derivatives were synthesized in good yields. The reactions are easy to be conducted under mild conditions. The mechanism study shows that the reaction might involve a cascade electrophilic iodocyclization/nucleophilic substitution pathway.

Key words: N-iodosuccinimide (NIS), alkenyl oximes, oxoazidation, isoxazolines

Cite this article

Haoran Liu, Junhao Yu, Tongyang Cao, Lin Qi, Lijing Wang. N-Iodosuccinimide-Promoted Cascade Oxoazidation of Alkenyl Oximes: Synthesis of Azido Isoxazolines[J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4220-4226.

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References 12

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Entry	Solvent	NIS/equiv.	NaN₃/equiv.	Temp./℃	Yield^b/%
1	DMSO	3.0	3.0	25	46
2	DCE	3.0	3.0	25	0
3	THF	3.0	3.0	25	0
4	DMA	3.0	3.0	25	65
5	DMF	3.0	3.0	25	85
6	DMF	2.0	3.0	25	67
7	DMF	4.0	3.0	25	63
8	DMF	3.0	2.0	25	80
9	DMF	3.0	4.0	25	75
10	DMF	3.0	3.0	40	84
11	DMF	3.0	3.0	60	80
12^c	DMF	3.0	3.0	25	71
13^c	DMF	3.0	3.0	25	67

Entry	Solvent	NIS/equiv.	NaN₃/equiv.	Temp./℃	Yield^b/%
1	DMSO	3.0	3.0	25	46
2	DCE	3.0	3.0	25	0
3	THF	3.0	3.0	25	0
4	DMA	3.0	3.0	25	65
5	DMF	3.0	3.0	25	85
6	DMF	2.0	3.0	25	67
7	DMF	4.0	3.0	25	63
8	DMF	3.0	2.0	25	80
9	DMF	3.0	4.0	25	75
10	DMF	3.0	3.0	40	84
11	DMF	3.0	3.0	60	80
12^c	DMF	3.0	3.0	25	71
13^c	DMF	3.0	3.0	25	67

N-碘代丁二酰亚胺促进烯基肟的串联氧叠氮化反应: 合成叠氮化异噁唑啉类化合物

N-Iodosuccinimide-Promoted Cascade Oxoazidation of Alkenyl Oximes: Synthesis of Azido Isoxazolines

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