Synthesis of Multi-substituted 1,4-Dihydroquinoline Derivatives from Morita-Baylis-Hillman (MBH) Carbonates

doi:10.6023/cjoc202008020

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (2): 677-687.DOI: 10.6023/cjoc202008020 Previous Articles Next Articles

Article

以森田-贝里斯-希尔曼(MBH)碳酸酯为原料合成多取代1,4-二氢喹啉类衍生物

史鸿燕¹, 钟莹¹^,^*(), 赵志刚¹^,^*()

1 西南民族大学化学与环境保护工程学院成都 610041

收稿日期:2020-08-12 修回日期:2020-09-08 发布日期:2020-09-30
通讯作者: 钟莹, 赵志刚
作者简介:
* Corresponding authors. E-mail: zyswun@163.com; zzg63129@163.com
基金资助:
西南民族大学中央高校基本科研业务费专项资金(2018NQN35)

Synthesis of Multi-substituted 1,4-Dihydroquinoline Derivatives from Morita-Baylis-Hillman (MBH) Carbonates

Hongyan Shi¹, Ying Zhong¹^,^*(), Zhigang Zhao¹^,^*()

1 College of Chemistry & Environment Protection Engineering, Southwest Minzu University, Chengdu 610041

Received:2020-08-12 Revised:2020-09-08 Published:2020-09-30
Contact: Ying Zhong, Zhigang Zhao
Supported by:
the Fundamental Research Funds for the Central Universities, Southwest Minzu University(2018NQN35)

1. cjoc202008020.pdf(6315KB)

Abstract

Using Morita-Baylis-Hillman (MBH) carbonates and active methylene compounds as raw materials, the key azide intermediates were obtained through two nucleophilic substitution reactions catalyzed by tertiary amine. Then, seventeen new multi-substituted 1,4-dihydroquinoline derivatives were obtained by sequential Staudinger/intramolecular aza-Wittig/isomeri- zation reactions of the azide intermediates with triphenylphosphine under mild conditions. The intermediates and target compounds are all new compounds, and their structures have been confirmed by IR, HRMS, ¹H NMR and ¹³C NMR techniques.

Key words: 1,4-dihydroquinolines, aza-Wittig reaction, Morita-Baylis-Hillman (MBH) carbonate, azide

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Hongyan Shi, Ying Zhong, Zhigang Zhao. Synthesis of Multi-substituted 1,4-Dihydroquinoline Derivatives from Morita-Baylis-Hillman (MBH) Carbonates[J]. Chinese Journal of Organic Chemistry, 2021, 41(2): 677-687.

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Fig. & Tab. 7

References 32

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Entry	Catalyst	Catalyst/ mol%	Solvent	T/℃	Time/h	Yield^b/%
1	DABCO	10	DCM	30	3	60
2	DMAP	10	DCM	30	3	44
3	DBU	10	DCM	30	4	NP
4	Et₃N	10	DCM	30	4	NR
5	CH₃ONa	10	DCM	30	4	NR
6	K₂CO₃	10	DCM	30	4	NR
7	DABCO	5.0	DCM	30	3	56
8	DABCO	7.5	DCM	30	3	65
9	DABCO	15	DCM	30	4	40
10	DABCO	20	DCM	30	4	NP
11	DABCO	7.5	CH₃CN	30	3	47
12	DABCO	7.5	THF	30	3	NP
13	DABCO	7.5	DMF	30	3	20
14	DABCO	7.5	DCE	30	3	45
15	DABCO	7.5	DCM	25	3	52
16	DABCO	7.5	DCM	35	3	70
17	DABCO	7.5	DCM	40	3	55

Entry	Catalyst	Catalyst/ mol%	Solvent	T/℃	Time/h	Yield^b/%
1	DABCO	10	DCM	30	3	60
2	DMAP	10	DCM	30	3	44
3	DBU	10	DCM	30	4	NP
4	Et₃N	10	DCM	30	4	NR
5	CH₃ONa	10	DCM	30	4	NR
6	K₂CO₃	10	DCM	30	4	NR
7	DABCO	5.0	DCM	30	3	56
8	DABCO	7.5	DCM	30	3	65
9	DABCO	15	DCM	30	4	40
10	DABCO	20	DCM	30	4	NP
11	DABCO	7.5	CH₃CN	30	3	47
12	DABCO	7.5	THF	30	3	NP
13	DABCO	7.5	DMF	30	3	20
14	DABCO	7.5	DCE	30	3	45
15	DABCO	7.5	DCM	25	3	52
16	DABCO	7.5	DCM	35	3	70
17	DABCO	7.5	DCM	40	3	55

以森田-贝里斯-希尔曼(MBH)碳酸酯为原料合成多取代1,4-二氢喹啉类衍生物

Synthesis of Multi-substituted 1,4-Dihydroquinoline Derivatives from Morita-Baylis-Hillman (MBH) Carbonates

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