Lewis酸催化下3-烷基-2-吲哚烯与α,β-不饱和N-磺酰基亚胺的[2+4]环化反应

doi:10.6023/cjoc202210037

有机化学 ›› 2023, Vol. 43 ›› Issue (6): 2178-2188.DOI: 10.6023/cjoc202210037 上一篇下一篇

研究论文

Lewis酸催化下3-烷基-2-吲哚烯与α,β-不饱和N-磺酰基亚胺的[2+4]环化反应

孙李星^a, 孙婷婷^a, 王海清^a, 吴淑芳^a, 王小烨^c, 刘天雅^b^,^*(), 张宇辰^a^,^*()

a 江苏师范大学化学与材料科学学院江苏徐州 221116
b 徐州医科大学附属医院麻醉科江苏徐州 221004
c 徐州医科大学江苏省麻醉学重点实验室江苏徐州 221004

收稿日期:2022-10-29 修回日期:2022-12-10 发布日期:2022-12-28
作者简介:
^† 共同第一作者
基金资助:
国家自然科学基金(22101103); 江苏省自然科学基金(BK20201018); 江苏省高层次创新创业人才引进、徐州市科技计划(KC21021); 江苏省大学生创新(202110320041Z)

Lewis Acid-Catalyzed [2+4] Cyclization of 3-Alkyl-2-vinylindoles with α,β-Unsaturated N-Sulfonyl Ketimines

Lixing Sun^a, Tingting Sun^a, Haiqing Wang^a, Shufang Wu^a, Xiaoye Wang^c, Tianya Liu^b,*(), Yuchen Zhang^a,*()

a School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou, Jiangsu 221116
b Department of Anesthesiology, The Affiliated Hospital of Xuzhou Medical University, Xuzhou, Jiangsu 221004
c Key Laboratory of Anesthesiology of Jiangsu Province, Xuzhou Medical University, Xuzhou, Jiangsu 221004

Received:2022-10-29 Revised:2022-12-10 Published:2022-12-28
Contact: * E-mail: zhangyc@jsnu.edu.cn; tianyaliu2004@163.com
About author:
^† These authors contributed equally to this work
Supported by:
National Natural Science Foundation of China(22101103); Natural Science Foundation of Jiangsu Province(BK20201018); High-level Innovative and Entrepreneurial Talents Introduction Plan of Jiangsu Province, the Technology Plan of Xuzhou City(KC21021); Undergraduate Students Project of Jiangsu Province(202110320041Z)

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摘要/Abstract

通过Lewis酸催化下3-烷基-2-吲哚烯与α,β-不饱和N-磺酰基亚胺的[2+4]环化反应, 以中等至良好的收率、极好的非对映选择性, 合成了具有潜在抗肿瘤活性的吲哚衍生哌啶类化合物. 该工作解决了3-烷基-2-吲哚烯参与的[2+4]环化反应中的挑战性问题, 丰富了3-烷基-2-吲哚烯化学的研究内容. 此外, 该反应为高原子经济性合成含吲哚母核的哌啶衍生物提供了新方法.

关键词: 3-烷基-2-吲哚烯, α,β-不饱和N-磺酰基亚胺, [2+4]环化反应, 吲哚衍生物

A Lewis acid-catalyzed [2+4] cyclization of 3-alkyl-2-vinylindoles with α,β-unsaturated N‑sulfonyl ketimines was established, and indole-containing piperidines with potential antitumor activity were synthesized in moderate to good yields (up to 95% yield) and generally excellent diastereoselectivities (up to>95:5 dr). This work has confronted the challenges in exploring the [2+4] cyclization of 3-alkyl-2-vinylindoles, which will enrich the chemistry of 3-alkyl-2-vinylindoles. In addition, this approach provides an atom-economic method for the synthesis of indole-containing piperidines.

Key words: 3-alkyl-2-vinylindole, α,β-unsaturated N-sulfonyl ketimine, [2+4] cyclization, indole derivative

引用此文

孙李星, 孙婷婷, 王海清, 吴淑芳, 王小烨, 刘天雅, 张宇辰. Lewis酸催化下3-烷基-2-吲哚烯与α,β-不饱和N-磺酰基亚胺的[2+4]环化反应[J]. 有机化学, 2023, 43(6): 2178-2188.

Lixing Sun, Tingting Sun, Haiqing Wang, Shufang Wu, Xiaoye Wang, Tianya Liu, Yuchen Zhang. Lewis Acid-Catalyzed [2+4] Cyclization of 3-Alkyl-2-vinylindoles with α,β-Unsaturated N-Sulfonyl Ketimines[J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2178-2188.

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参考文献 15

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Entry	LA	Solvent	dr^b	Yield^c/%
1	Cu(OTf)₂	CH₃CN	>95:5	39
2	Mg(OTf)₂	CH₃CN	—	N.R.
3	Fe(OTf)₃	CH₃CN	>95:5	57
4	ZnCl₂	CH₃CN	—	Trace
5	Y(OTf)₃	CH₃CN	—	Trace
6	Sc(OTf)₃	CH₃CN	>95:5	76
7	Yb(OTf)₃	CH₃CN	—	Trace
8	Zn(OTf)₂	CH₃CN	—	N.R.
9	Sc(OTf)₃	DCE	83:17	53
10	Sc(OTf)₃	THF	—	Trace
11	Sc(OTf)₃	Acetone	—	Trace
12	Sc(OTf)₃	AcOEt	>95:5	56
13	Sc(OTf)₃	toluene	75:25	21

Entry	LA	Solvent	dr^b	Yield^c/%
1	Cu(OTf)₂	CH₃CN	>95:5	39
2	Mg(OTf)₂	CH₃CN	—	N.R.
3	Fe(OTf)₃	CH₃CN	>95:5	57
4	ZnCl₂	CH₃CN	—	Trace
5	Y(OTf)₃	CH₃CN	—	Trace
6	Sc(OTf)₃	CH₃CN	>95:5	76
7	Yb(OTf)₃	CH₃CN	—	Trace
8	Zn(OTf)₂	CH₃CN	—	N.R.
9	Sc(OTf)₃	DCE	83:17	53
10	Sc(OTf)₃	THF	—	Trace
11	Sc(OTf)₃	Acetone	—	Trace
12	Sc(OTf)₃	AcOEt	>95:5	56
13	Sc(OTf)₃	toluene	75:25	21

Entry	R/R¹/R² (1)	3	dr^b	Yield^c/%
1	Me/H/Ph (1a)	3aa	>95:5	76
2	Et/H/Ph (1b)	3ba	>95:5	64
3	Bn/H/Ph (1c)	3ca	78:22	62
4	Ph/H/Ph (1d)	3da	85:15	68
5	Me/5-Cl/Ph (1e)	3ea	>95:5	86
6	Me/5-Me/Ph (1f)	3fa	88:12	91
7	Me/6-Cl/Ph (1g)	3ga	>95:5	87
8	Me/H/o-BrC₆H₄ (1h)	3ha	83:17	62
9	Me/H/o-FC₆H₄ (1i)	3ia	91:9	61
10	Me/H/m-MeOC₆H₄ (1j)	3ja	89:11	89
11	Me/H/m-MeC₆H₄ (1k)	3ka	90:10	78
12	Me/H/m-FC₆H₄ (1l)	3la	93:7	65
13	Me/H/m-BrC₆H₄ (1m)	3ma	92:8	70
14	Me/H/p-MeC₆H₄ (1n)	3na	78:22	75

Entry	R/R¹/R² (1)	3	dr^b	Yield^c/%
1	Me/H/Ph (1a)	3aa	>95:5	76
2	Et/H/Ph (1b)	3ba	>95:5	64
3	Bn/H/Ph (1c)	3ca	78:22	62
4	Ph/H/Ph (1d)	3da	85:15	68
5	Me/5-Cl/Ph (1e)	3ea	>95:5	86
6	Me/5-Me/Ph (1f)	3fa	88:12	91
7	Me/6-Cl/Ph (1g)	3ga	>95:5	87
8	Me/H/o-BrC₆H₄ (1h)	3ha	83:17	62
9	Me/H/o-FC₆H₄ (1i)	3ia	91:9	61
10	Me/H/m-MeOC₆H₄ (1j)	3ja	89:11	89
11	Me/H/m-MeC₆H₄ (1k)	3ka	90:10	78
12	Me/H/m-FC₆H₄ (1l)	3la	93:7	65
13	Me/H/m-BrC₆H₄ (1m)	3ma	92:8	70
14	Me/H/p-MeC₆H₄ (1n)	3na	78:22	75

Entry	Ar (2)	3	dr^b	Yield^c/%
1	C₆H₅(2a)	3aa	>95:5	76
2	o-MeOC₆H₄(2b)	3ab	93:7	75
3	o-ClC₆H₄(2c)	3ac	>95:5	62
4	m-MeOC₆H₄ (2d)	3ad	91:9	76
5	m-MeC₆H₄ (2e)	3ae	>95:5	62
6	p-MeOC₆H₄ (2f)	3af	88:12	71
7	p-FC₆H₄ (2g)	3ag	>95:5	89
8	p-ClC₆H₄ (2h)	3ah	>95:5	95
9	2-Naphthyl (2i)	3ai	>95:5	71
10	3-Thienyl (2j)	3aj	87:13	80
11	5-Methyl-2-furyl (2k)	3ak	>95:5	56

Lewis酸催化下3-烷基-2-吲哚烯与α,β-不饱和N-磺酰基亚胺的[2+4]环化反应

Lewis Acid-Catalyzed [2+4] Cyclization of 3-Alkyl-2-vinylindoles with α,β-Unsaturated N-Sulfonyl Ketimines

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Entry	T/℃	n(1a):n(2a)	x	dr^b	Yield^c/%
1	70	1:2	1	>95:5	76
2	50	1:2	1	>95:5	22
3	90	1:2	1	>95:5	53
4	70	1:1.5	1	>95:5	22
5	70	1:3	1	>95:5	72
6	70	1.5:1	1	>95:5	55
7	70	2:1	1	>95:5	68
8	70	3:1	1	>95:5	62
9	70	1:2	0.5	>95:5	71
10	70	1:2	2	>95:5	70
11^d	70	1:2	1	>95:5	68

Entry	T/℃	n(1a):n(2a)	x	dr^b	Yield^c/%
1	70	1:2	1	>95:5	76
2	50	1:2	1	>95:5	22
3	90	1:2	1	>95:5	53
4	70	1:1.5	1	>95:5	22
5	70	1:3	1	>95:5	72
6	70	1.5:1	1	>95:5	55
7	70	2:1	1	>95:5	68
8	70	3:1	1	>95:5	62
9	70	1:2	0.5	>95:5	71
10	70	1:2	2	>95:5	70
11^d	70	1:2	1	>95:5	68