Arylsulfonylative spiro-Tricyclization of N-Hydroxylethyl- N-arylpropiolamides

doi:10.6023/cjoc202104046

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (9): 3652-3659.DOI: 10.6023/cjoc202104046 Previous Articles Next Articles

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N-羟乙基-N-芳基丙炔酰胺的芳基磺酰化及螺-三环化反应

任尚峰^a, 王玉超^a, 刘晋彪^a^,^*(), 邱观音生^a^,^b^,^*()

a 江西理工大学材料冶金化学学部江西赣州 341000
b 嘉兴学院生物与化学工程学院浙江嘉兴 314001

收稿日期:2021-04-21 修回日期:2021-05-20 发布日期:2021-06-22
通讯作者: 刘晋彪, 邱观音生
基金资助:
国家自然科学基金(21772067); 国家自然科学基金(21762018); 国家自然科学基金(21961014); 江西省自然科学基金(20171BAB213008); 江西省自然科学基金(20192BCBL23009); 江西省自然科学基金(20202BABL203005); 江西省青年井冈学者奖励计划资助项目.

Arylsulfonylative spiro-Tricyclization of N-Hydroxylethyl- N-arylpropiolamides

Shangfeng Ren^a, Yuchao Wang^a, Jinbiao Liu^a(), Guanyinsheng Qiu^a^,^b()

a Faculty of Materials Metallurgy and Chemistry, Jiangxi University of Science and Technology, Ganzhou, Jiangxi 341000
b College of Biological, Chemical Sciences and Engineering, Jiaxing University, Jiaxing, Zhejiang 314001

Received:2021-04-21 Revised:2021-05-20 Published:2021-06-22
Contact: Jinbiao Liu, Guanyinsheng Qiu
Supported by:
National Natural Science Foundation of China(21772067); National Natural Science Foundation of China(21762018); National Natural Science Foundation of China(21961014); Natural Science Foundation of Jiangxi Province(20171BAB213008); Natural Science Foundation of Jiangxi Province(20192BCBL23009); Natural Science Foundation of Jiangxi Province(20202BABL203005); Youth Jinggang Scholars Program in Jiangxi Province.

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Abstract

A facile procedure is reported for the synthesis of various 1-aryl-2-tosyl-5,6-dihydrobenzo[b]pyrrolo[2,1-c][1,4]- oxazin-3(7aH)-one via a radical arylsulfonylation-induced ipso-cyclization-ortho-cyclization sequence of N-hydroxylethyl-N- arylpropiolamides in the presence of tetra-n-butylammonium iodide (TBAI) and oxone. The radical cyclization sequence involves a sulfonyl radical α-addition into the alkyne, ipso-cyclization, and ortho-trapping of the spirocyclic intermediate.

Key words: spiro-tricyclization, arylsulfonylation, radical, ortho-capture

Cite this article

Shangfeng Ren, Yuchao Wang, Jinbiao Liu, Guanyinsheng Qiu. Arylsulfonylative spiro-Tricyclization of N-Hydroxylethyl- N-arylpropiolamides[J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3652-3659.

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Entry	Additive	Oxidant	Temp./℃	Solvent	Yield^b
1	I₂O₅	Oxone	80	1,4-二氧六环	26%
2	I₂O₅	(NH₄)₂S₂O₈	80	1,4-二氧六环	12%
3	I₂O₅	间氯过氧苯甲酸	80	1,4-二氧六环	15%
4	I₂O₅	过氧化二苯甲酰	80	1,4-二氧六环	Trace
5	I₂O₅	过氧化二叔丁基	80	1,4-二氧六环	18%
6	TBAB	Oxone	80	1,4-二氧六环	ND
7	TBAI	Oxone	80	1,4-二氧六环	50%
8	I₂	Oxone	80	1,4-二氧六环	NR
9	TBAI	Oxone	80	1,2-二氯乙烷	36%
10	TBAI	Oxone	80	DMF	NR
11	TBAI	Oxone	80	甲苯	53%
12	TBAI	Oxone	80	乙腈	40%
13	TBAI (50 mol%)	Oxone	80	甲苯	26%
14	TBAI	Oxone	r.t.	甲苯	Trace
15	TBAI	Oxone	60	甲苯	25%
16	TBAI	Oxone	100	甲苯	36%
17	TBAI	—	80	甲苯	NR

Entry	Additive	Oxidant	Temp./℃	Solvent	Yield^b
1	I₂O₅	Oxone	80	1,4-二氧六环	26%
2	I₂O₅	(NH₄)₂S₂O₈	80	1,4-二氧六环	12%
3	I₂O₅	间氯过氧苯甲酸	80	1,4-二氧六环	15%
4	I₂O₅	过氧化二苯甲酰	80	1,4-二氧六环	Trace
5	I₂O₅	过氧化二叔丁基	80	1,4-二氧六环	18%
6	TBAB	Oxone	80	1,4-二氧六环	ND
7	TBAI	Oxone	80	1,4-二氧六环	50%
8	I₂	Oxone	80	1,4-二氧六环	NR
9	TBAI	Oxone	80	1,2-二氯乙烷	36%
10	TBAI	Oxone	80	DMF	NR
11	TBAI	Oxone	80	甲苯	53%
12	TBAI	Oxone	80	乙腈	40%
13	TBAI (50 mol%)	Oxone	80	甲苯	26%
14	TBAI	Oxone	r.t.	甲苯	Trace
15	TBAI	Oxone	60	甲苯	25%
16	TBAI	Oxone	100	甲苯	36%
17	TBAI	—	80	甲苯	NR

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N-羟乙基-N-芳基丙炔酰胺的芳基磺酰化及螺-三环化反应

Arylsulfonylative spiro-Tricyclization of N-Hydroxylethyl- N-arylpropiolamides

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