Synthesis of Fused Pyridines via Microwave-Assisted [3+3] Cyclization

doi:10.6023/cjoc202102018

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (4): 1563-1571.DOI: 10.6023/cjoc202102018 Previous Articles Next Articles

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利用微波辅助[3+3]环化反应合成稠合吡啶衍生物

吴亚男^a^,^b^,^*(), 杜建宇^b, 郝文娟^b, 姜波^b^,^*()

a 南通大学化学化工学院江苏南通 226019
b 江苏师范大学化学与材料科学学院江苏徐州 221116

收稿日期:2021-02-04 修回日期:2021-02-10 发布日期:2021-02-26
通讯作者: 吴亚男, 姜波
基金资助:
国家自然科学基金(21971090); 江苏省品牌专业基金资助项目

Synthesis of Fused Pyridines via Microwave-Assisted [3+3] Cyclization

Yanan Wu^a^,^b^,^*(), Jianyu Du^b, Wenjuan Hao^b, Bo Jiang^b^,^*()

a School of Chemistry and Chemical Engineering, Nantong University, Nantong, Jiangsu 226019
b School of Chemistry & Materials Science, Jiangsu Normal University, Xuzhou, Jiangsu 221116

Received:2021-02-04 Revised:2021-02-10 Published:2021-02-26
Contact: Yanan Wu, Bo Jiang
About author:
* Corresponding author. E-mail: 1498280030@qq.com;
E-mail: jiangchem@jsnu.edu.cn
Supported by:
National Natural Science Foundation of China(21971090); Top-notch Academic Programs Project of Jiangsu Higher Education Institutions

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Abstract

A new microwave-assisted p-TsOH-promoted [3+3] cyclization was developed. By using the characteristics of enaminones or enamino lactones as 1,3-dinucleaphilic reagents and propargyl alcohols as 1,3-electrophilic reagents, p-TsOH- promoted [3+3] cyclization of these substrates at 70 ℃ was carried out in acetic acid under microwave irradiation, regioselectively affording 2,2-diaryl-substituted tetrahydroquinoline-5(1H)-ones and 2,2-diaryl-substituted dihydrofuro[3,4-b]pyridin- 5-ones in good yields. The reaction can be completed within a short period (30 min) by microwave synthetic technology, in which water was the sole by-product. This method features simple and available starting materials, simple operation and wide substrate scope, and provides a green, economic, and efficient synthetic strategy for the construction of fused pyridine skeleton with potential application, which is consistent with the concept of green chemistry.

Key words: microwave synthesis, [3+3] cyclization, quinoline-5(1H)-one, furo[3,4-b]pyridin-5-one, green chemistry

Cite this article

Yanan Wu, Jianyu Du, Wenjuan Hao, Bo Jiang. Synthesis of Fused Pyridines via Microwave-Assisted [3+3] Cyclization[J]. Chinese Journal of Organic Chemistry, 2021, 41(4): 1563-1571.

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Entry	Promotor (equiv.)	Solvent	Temp./℃	Yield^b/%
1	p-TsOH (1.0)	Acetone	100	N.R.
2	p-TsOH (1.0)	DCE	100	N.R.
3	p-TsOH (1.0)	DCM	100	Trace
4	p-TsOH (1.0)	MeCN	100	30
5	p-TsOH (1.0)	Toluene	100	Trace
6	p-TsOH (1.0)	EtOH	100	Trace
7	p-TsOH (1.0)	HOAc	100	58
8	p-TsOH (0.5)	HOAc	100	45
9	p-TsOH (2.0)	HOAc	100	55
10	BF₃?Et₂O (1.0)	HOAc	100	37
11	TFA (1.0)	HOAc	100	21
12	TfOH (1.0)	HOAc	100	Trace
13	p-TsOH (1.0)	HOAc	90	61
14	p-TsOH (1.0)	HOAc	80	65
15	p-TsOH (1.0)	HOAc	70	70
16	p-TsOH (1.0)	HOAc	60	60

Entry	Promotor (equiv.)	Solvent	Temp./℃	Yield^b/%
1	p-TsOH (1.0)	Acetone	100	N.R.
2	p-TsOH (1.0)	DCE	100	N.R.
3	p-TsOH (1.0)	DCM	100	Trace
4	p-TsOH (1.0)	MeCN	100	30
5	p-TsOH (1.0)	Toluene	100	Trace
6	p-TsOH (1.0)	EtOH	100	Trace
7	p-TsOH (1.0)	HOAc	100	58
8	p-TsOH (0.5)	HOAc	100	45
9	p-TsOH (2.0)	HOAc	100	55
10	BF₃?Et₂O (1.0)	HOAc	100	37
11	TFA (1.0)	HOAc	100	21
12	TfOH (1.0)	HOAc	100	Trace
13	p-TsOH (1.0)	HOAc	90	61
14	p-TsOH (1.0)	HOAc	80	65
15	p-TsOH (1.0)	HOAc	70	70
16	p-TsOH (1.0)	HOAc	60	60

利用微波辅助[3+3]环化反应合成稠合吡啶衍生物

Synthesis of Fused Pyridines via Microwave-Assisted [3+3] Cyclization

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