N-Heterocyclic Carbene (NHC)-Catalyzed [3+2] Cycloaddition to Highly Diastereoselective Synthesis of Spirooxindole Dihydrofuran Fused Pyrazolone Compounds

doi:10.6023/cjoc202309004

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (4): 1301-1310.DOI: 10.6023/cjoc202309004 Previous Articles Next Articles

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氮杂环卡宾(NHC)催化[3+2]环加成反应高非对映选择性地构建螺氧吲哚二氢呋喃稠合吡唑啉酮化合物

刘岩, 王晓梅, 何林^*(), 李师伍, 赵志飞^*()

石河子大学化学化工学院化工绿色过程省部共建国家重点实验室培育基地新疆石河子 832000

收稿日期:2023-09-04 修回日期:2023-11-11 发布日期:2023-11-23
基金资助:
国家自然科学基金(22101188); 石河子大学(2022ZK003); 石河子大学(RCZK202001)

N-Heterocyclic Carbene (NHC)-Catalyzed [3+2] Cycloaddition to Highly Diastereoselective Synthesis of Spirooxindole Dihydrofuran Fused Pyrazolone Compounds

Yan Liu, Xiaomei Wang, Lin He(), Shiwu Li, Zhifei Zhao()

State Key Laboratory Incubation Base for Green Processing of Chemical Engineering, School School of Chemistry and Chemical Engineering, Shihezi University, Shihezi, Xinjiang 832000

Received:2023-09-04 Revised:2023-11-11 Published:2023-11-23
Contact: * E-mail: zhaozf@shzu.edu.cn; helin@shzu.edu.cn
Supported by:
National Natural Science Foundation of China(22101188); Shihezi University(2022ZK003); Shihezi University(RCZK202001)

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Abstract

An efficient N-heterocyclic carbene (NHC)-catalyzed [3+2] cycloaddition of isatin-derived enal and pyrazole-4,5- diones to directly synthesis of spirooxindole dihydrofuran fused pyrazolone compounds containing two vicinal spirocenters was disclosed. This approach was qualified with broad substrate scope, achieving moderate to excellent yield (41%~99%) and general to excellent diastereoselective (2∶1~>20∶1 dr). Furthermore, the reaction has the advantages of mild reaction conditions and easy operation, and the gram scale reaction can also proceed smoothly. This study provides a new synthetic methodology for the efficient construction of multi-functionalized spirooxindole dihydrofuran fused pyrazolone compounds.

Key words: N-heterocyclic carbene, cycloaddition, spirooxindole, pyrazolone

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Yan Liu, Xiaomei Wang, Lin He, Shiwu Li, Zhifei Zhao. N-Heterocyclic Carbene (NHC)-Catalyzed [3+2] Cycloaddition to Highly Diastereoselective Synthesis of Spirooxindole Dihydrofuran Fused Pyrazolone Compounds[J]. Chinese Journal of Organic Chemistry, 2024, 44(4): 1301-1310.

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References 18

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Entry	Catalyst	Base	Solvent	Yield^b/%	dr^c
1	A	K₂CO₃	THF	Trace	—
2	C	K₂CO₃	THF	Trace	—
3	D	K₂CO₃	THF	Trace	—
4	E	K₂CO₃	THF	Trace	—
5	F	K₂CO₃	THF	Trace	—
6	B	K₂CO₃	THF	86	18∶1
7	B	Na₂CO₃	THF	85	6∶1
8	B	Cs₂CO₃	THF	82	8∶1
9	B	NaOH	THF	77	8∶1
10	B	KOH	THF	65	4∶1
11	B	Et₃N	THF	83	10∶1
12	B	K₂CO₃	CH₂Cl₂	39	3∶1
13	B	K₂CO₃	CH₃CN	Trace	—
14	B	K₂CO₃	Toluene	67	13∶1

Entry	Catalyst	Base	Solvent	Yield^b/%	dr^c
1	A	K₂CO₃	THF	Trace	—
2	C	K₂CO₃	THF	Trace	—
3	D	K₂CO₃	THF	Trace	—
4	E	K₂CO₃	THF	Trace	—
5	F	K₂CO₃	THF	Trace	—
6	B	K₂CO₃	THF	86	18∶1
7	B	Na₂CO₃	THF	85	6∶1
8	B	Cs₂CO₃	THF	82	8∶1
9	B	NaOH	THF	77	8∶1
10	B	KOH	THF	65	4∶1
11	B	Et₃N	THF	83	10∶1
12	B	K₂CO₃	CH₂Cl₂	39	3∶1
13	B	K₂CO₃	CH₃CN	Trace	—
14	B	K₂CO₃	Toluene	67	13∶1

氮杂环卡宾(NHC)催化[3+2]环加成反应高非对映选择性地构建螺氧吲哚二氢呋喃稠合吡唑啉酮化合物

N-Heterocyclic Carbene (NHC)-Catalyzed [3+2] Cycloaddition to Highly Diastereoselective Synthesis of Spirooxindole Dihydrofuran Fused Pyrazolone Compounds

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