溶剂控制三氟甲烷磺酸钪催化2-(杂)芳基-N-磺酰基吖丁啶开环反应: 烯丙胺/1,3-噁嗪衍生物的合成

doi:10.6023/cjoc202403039

有机化学 ›› 2024, Vol. 44 ›› Issue (9): 2796-2809.DOI: 10.6023/cjoc202403039 上一篇下一篇

研究论文

溶剂控制三氟甲烷磺酸钪催化2-(杂)芳基-N-磺酰基吖丁啶开环反应: 烯丙胺/1,3-噁嗪衍生物的合成

朱洁^a, 汤思丹^a, 阚秀妹^a, 凡士柱^a, 王鹏飞^a, 杨培俊^a^,^b^,^*()

a 安徽工程大学化学与环境工程学院功能配合物材料化学与应用安徽省重点实验室安徽芜湖 241000
b 安徽师范大学化学与材料科学学院分子基材料省级实验室安徽芜湖 241002

收稿日期:2024-03-26 修回日期:2024-05-14 发布日期:2024-05-30
通讯作者: 杨培俊
基金资助:
国家自然科学基金(22001007); 安徽工程大学科研基金(2020YQQ025); 安徽省重点分子基材料省级实验室开放基金(fzj22012)

Solvent-Controlled Sc(OTf)₃-Catalyzed Ring Opening Reaction of 2-(Hetero)aryl-N-sulfonylazetidines: Synthesis of Allylic Amines/1,3-Oxazinane Derivatives

Jie Zhu^a, Sidan Tang^a, Xiumei Kan^a, Shizhu Fan^a, Pengfei Wang^a, Peijun Yang^a^,^b()

a Anhui Province Key Laboratory of Functional Coordinated Complexes for Materials Chemistry and Application, School of Chemical and Environmental Engineering, Anhui Polytechnic University, Wuhu, Anhui 241000
b Anhui Laboratory of Molecular-Based Materials, College of Chemistry and Materials Science, Anhui Normal University, Wuhu, Anhui 241002

Received:2024-03-26 Revised:2024-05-14 Published:2024-05-30
Contact: Peijun Yang
Supported by:
National Natural Science Foundation of China(22001007); Anhui Engineering University Scientific Research Foundation(2020YQQ025); Anhui Laboratory Molecular-Based Materials Open Fund(fzj22012)

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摘要/Abstract

烯丙胺和1,3-噁嗪烷是有机合成和医药工业中有重要价值的分子骨架. 报道了一种通过溶剂控制稀土金属路易斯酸催化2-(杂)芳基-N-磺酰基吖丁啶与醛环加成合成1,3-噁嗪烷以及自身开环异构化合成烯丙胺. 这两种反应具有底物适用范围广、催化剂用量低、反应条件温和、产率高和区域选择性好等特点, 并通过将产物三步转化为萘替酚、阿拉明和阿拉明SG证明了其实用价值.

关键词: 稀土金属路易斯酸, 溶剂控制, 吖丁啶, 区域选择性, 开环反应

Allylic amines and 1,3-oxazinanes are valuable molecular skeletons in organic synthesis and pharmaceutical industry. A straightforward way to such two types of compounds by solvent-controlled rare-earth metal Lewis acid-catalyzed transformations of 2-(hetero)aryl-N-sulfonylazetidines: the ring-opening isomerization of azetidines to allylic amines and the annulation of azetidines with aldehydes to 1,3-oxazinanes are reported. These two reactions feature scalability, low catalyst loading, mild reaction conditions, excellent yields and regioselectivity with demonstrated utility in three-step product transformations to naftifine, abamine and abamine SG.

Key words: rare-earth metal Lewis acid, solvent control, azetidine, regioselectivity, ring opening reaction

引用此文

朱洁, 汤思丹, 阚秀妹, 凡士柱, 王鹏飞, 杨培俊. 溶剂控制三氟甲烷磺酸钪催化2-(杂)芳基-N-磺酰基吖丁啶开环反应: 烯丙胺/1,3-噁嗪衍生物的合成[J]. 有机化学, 2024, 44(9): 2796-2809.

Jie Zhu, Sidan Tang, Xiumei Kan, Shizhu Fan, Pengfei Wang, Peijun Yang. Solvent-Controlled Sc(OTf)₃-Catalyzed Ring Opening Reaction of 2-(Hetero)aryl-N-sulfonylazetidines: Synthesis of Allylic Amines/1,3-Oxazinane Derivatives[J]. Chinese Journal of Organic Chemistry, 2024, 44(9): 2796-2809.

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参考文献 14

[1]	(a) Weiner, B.; Baeza, A.; Jerphagnon, T.; Feringa, B. L. J. Am. Chem. Soc. 2009, 131, 9473.
	(b) Zhao, X.; Liu, D.; Guo, H.; Liu, Y.; Zhang, W. J. Am. Chem. Soc. 2011, 133, 19354.
	(c) Roberts, D. D.; Mclaughlin, M. G. Org. Lett. 2021, 23, 4463.
	(d) Kim, J.; Kim, S.; Choi, G.; Lee, G. S.; Kim, D.; Choi, J.; Ihee, H.; Hong, S.-H. Chem. Sci. 2021, 12, 1915.
[2]	Selected examples for drugs and natural products, see: (a) Fagbemil, O.; Kane, K. A.; McDonald, F. M.; Parratt, J. R.; Rothaul, A. L. Br. J. Pharmacol. 1984, 83, 299. pmid: 2229523
	(b) Petranyi, G.; Ryder, N. S.; Stütz, A. Science 1984, 224, 1239. pmid: 2229523
	(c) Birnbaum, J. E. J. Am. Acad. Dermatol. 1990, 23, 782. pmid: 2229523
	(d) Hagihara, M.; Anthony, N. J.; Stout, T. J.; Clardy, J.; Schreiber, S. L. J. Am. Chem. Soc. 1992, 114, 6568. pmid: 2229523
	(e) Cui, Z.; Chen, Y.-J.; Gao, W.-Y.; Feng, C.-G.; Lin, G.-Q. Org. Lett. 2014, 16, 1016. pmid: 2229523
[3]	For selected examples, see: (a) Wang, X.; Dong, Y.; Sun, J.; Xu, X.; Li, R.; Hu, Y. J. Org. Chem. 2005, 70, 1897. pmid: 31943983
	(b) Okimoto, M.; Ohashi, K.; Yamamori, H.; Nishikawa, S.; Hoshi, M.; Yoshida, T. Synthesis 2012, 44, 1315. pmid: 31943983
	(c) He, S.; Li, P.; Dai, X.; McComas, C. C.; Huang, H.; Zhan, C.; Chang, L. Y.; Liu, Y.; Chen, S.; Lai, Z.; Liu, H.; Yin, J.; Dang, Q.; Xiao, D.; Zorn, N.; Peng, X.; Nargund, R. P.; Palani, A. Tetrahedron Lett. 2013, 54, 3755. pmid: 31943983
	(d) Yao, C.-Z.; Xiao, Z.-F.; Liu, J.; Ning, X.-S.; Kang, Y.-B. Org. Lett. 2014, 16, 2498. pmid: 31943983
	(e) Cui, S.-S.; Huang, R.; Luo, D. -Y.; Yan, S.-J.; Lin, J. Eur. J. Org. Chem. 2017, 24, 3442. pmid: 31943983
	(f) Xue, Q.; Bi, F.; Zhai, L.; Guo, T.; Zhang, J.; Zhang, S.; Wang, B.; Zhang, J. ChemPlusChem 2019, 84, 913. doi: 10.1002/cplu.201900322 pmid: 31943983
	(g) Wu, G.; Wang, T.; Jiang, Z.; Liu, S.; Sun, C. ACS Omega 2021, 6, 8239. pmid: 31943983
[4]	(a) Shimojima, Y.; Hayashi, H.; Ooka, T.; Shibukawa, M.; Iitaka, Y. Tetrahedron Lett. 1982, 23, 5435.
	(b) Shimojima, Y.; Hayashi, H.; Ooka, T.; Shibukawa, M.; Iitaka, Y. Tetrahedron 1984, 40, 2519.
[5]	(a) Mughal, H.; Szostak, M. Org. Biomol. Chem. 2021, 19, 3274.
	(b) Li, Z.; Wang, Y.; Liu, D.; Ning, L.; Pu, M.; Lin, L.; Feng, X. Org. Lett. 2023, 25, 7612.
[6]	Ghorai, M. K.; Das, K.; Kumar, A. Tetrahedron Lett. 2007, 48, 4373.
[7]	Ghorai, M. K.; Kumar, A.; Das, K. Org. Lett. 2007, 9, 5441. pmid: 18020346
[8]	Pearson, R. G. J. Am. Chem. Soc. 1963, 85, 3533.
[9]	(a) Mikami, K.; Terada, M.; Matsuzawa, H. Angew. Chem., Int. Ed. 2002, 41, 3554.
	(b) Shen, K.; Liu, X.; Lin, l.; Feng, X. Chem. Sci. 2012, 3, 327.
	(c) Wu, Y.-H.; Zhang, L.-Y.; Wang, N.-X.; Xing, Y. Catal. Rev. 2020, 64, 679.
	(d) Guan, Y.-W.; Chang, K.-J.; Sun, Q.-L.; Xu, X. Chin. J. Org. Chem. 2022, 42, 1326 (in Chinese).
	(管怡雯, 常克俭, 孙千林, 徐信, 有机化学, 2022, 42, 1326.) doi: 10.6023/cjoc202112008
[10]	(a) Kobayashi, S.; Sugiura, M.; Kitagawa, H.; Lam, W. W. L. Chem. Rev. 2002, 102, 2227. pmid: 12059268
	(b) Luo, S.; Zhu, L.; Talukdar, A.; Zhang, G.; Mi, X.; Cheng, J.-P.; Wang, P. G. Mini-Rev. Org. Chem. 2005, 2, 177. pmid: 12059268
	(c) Sueya Prakash, G. K.; Mathew, T.; Olah, D. A. Acc. Chem. Res. 2012, 45, 565. pmid: 12059268
	(d) Wang, S.; Chai, Z.; Zhou, S.; Wang, S.; Zhu, X.; Wei, Y. Org. Lett. 2013, 15, 2628. pmid: 12059268
[11]	For selected recent examples, see: (a) Jia, R.-H.; Liu, S.; Wang, S.-C.; Hao, W.-J.; Jiang, B. Chin. J. Org. Chem. 2022, 42, 2814 (in Chinese).
	(贾润红, 刘帅, 王世超, 郝文娟, 姜波, 有机化学, 2022, 42, 2814.) doi: 10.6023/cjoc202204057
	(b) Ji, X.-S.; Zuo, H.-D.; Shen, Y.-T.; Hao, W.-J.; Tu, S.-J.; Jiang, B. Chem. Commun. 2022, 58, 10420.
	(c) Zhou, Y.; Chen, H.; Lei, P.-P.; Gui, C.-M.; Wang, H.-F.; Yan, Q.-J.; Wang, W.; Chen, F. Chin. Chem. Lett. 2022, 33, 4850.
	(d) Chen, J.-Y.; Bai, D.-C.; Guo, X.-L.; Wang, Y.-Y.; Li, X.-W. Chin. Chem. Lett. 2022, 33, 5056.
[12]	For selected examples, see: (a) Ryder, N. S.; Dupont, M. C. Biochem. J. 1985, 230, 765. pmid: 3877503
	(b) Stutz, A.; Georgopoulos, A.; Granitzer, W.; Petranyi, G.; Berneyt, D. J. Med. Chem. 1986, 29, 112. pmid: 3877503
	(c) Sun, J.; Zhang, Y.; Su, J.; Dai, T.; Chen, J.; Zhang, L.; Wang, H.; Liu, W.; Huang, M.; Chen, Z. Dyes Pigm. 2020, 179, 108392. pmid: 3877503
	(d) An, Y.; Dong, Y.; Min, L.; Zhao, L.; Zhao, D.; Han, J.; Sun, B. ACS Med. Chem. Lett. 2020, 11, 1152. pmid: 3877503
[13]	(a) Han, S.-Y.; Kitahata, N.; Saito, T.; Kobayashi, M.; Shinozaki, K.; Yoshidaa, S.; Asami, T. Bioorg. Med. Chem. Lett. 2004, 14, 3033.
	(b) Han, S.-Y.; Kitahata, N.; Sekimata, K.; Saito, T.; Kobayashi, M.; Nakashima, K.; Yamaguchi-Shinozaki, K.; Shinozaki, K.; Yoshida, S.; Asami, T. Plant Physiol. 2004, 135, 1574.
	(c) Kitahata, N.; Han, S.-Y.; Noji, N.; Saito, T.; Kobayashi, M.; Nakano, T.; Kuchitsu, K.; Shinozaki, K.; Yoshida, S.; Matsumoto, S.; Tsujimotoa, M.; Asami, T. Bioorg. Med. Chem., 2006, 14, 5555.
[14]	(a) Nishikata, T.; Lipshutz, B. H. Org. Lett. 2009, 11, 2377. doi: 10.1021/ol900235s pmid: 19402681
	(b) Prediger, P.; Barbosa, L. F.; enisson, Y. G.; Correia, C. R. D. J. Org. Chem. 2011, 76, 7737. pmid: 19402681
	(c) Vaidya, G. N.; Nagpure, M.; Kumar, D. ACS Sustainable Chem. Eng. 2021, 9, 1846. pmid: 19402681

Entry	Lewis acid (x mol%)	Solvent	T/℃	t	Yield^b/%
Entry	Lewis acid (x mol%)	Solvent	T/℃	t	3aa^c	6a
1	Sc(OTf)₃ (1)	CH₂Cl₂	25	1 min	95	5
2	Cu(OTf)₂(1)	CH₂Cl₂	25	1 min	73	6
3	Y(OTf)₃ (1)	CH₂Cl₂	25	0.2 h	93	7
4	Sm(OTf)₃ (1)	CH₂Cl₂	25	0.25 h	88	8
5	Eu(OTf)₃ (1)	CH₂Cl₂	25	0.3 h	89	9
6	Yb(OTf)₃ (1)	CH₂Cl₂	25	0.15 h	93	7
7	Lu(OTf)₃ (1)	CH₂Cl₂	25	0.35 h	94	6
8	Sc(OTf)₃ (5)	CH₂Cl₂	25	1 min	87	13
9	Sc(OTf)₃ (1)	ClCH₂CH₂Cl	25	1 min	98	2
10	Sc(OTf)₃ (1)	DMF	25	24 h	NR	NR
11	Sc(OTf)₃ (1)	DMSO	25	24 h	NR	NR
12	Sc(OTf)₃ (1)	CH₃CN	25	1 min	32	0
13	Sc(OTf)₃ (1)	THF	25	4 h	35	65
14	Sc(OTf)₃ (1)	Toluene	25	1 min	90	6
15	Sc(OTf)₃ (1)	THF	30	2.5 h	11	89
16	Sc(OTf)₃ (1)	THF	35	1.5 h	40	60
17^d	Sc(OTf)₃ (1)	THF	30	9 h	—	88
18^e	Sc(OTf)₃ (0.05)	ClCH₂CH₂Cl	25	16 h	94	4
19^f	Sc(OTf)₃ (0.1)	THF	45	144 h	—	90

Entry	Lewis acid (x mol%)	Solvent	T/℃	t	Yield^b/%
Entry	Lewis acid (x mol%)	Solvent	T/℃	t	3aa^c	6a
1	Sc(OTf)₃ (1)	CH₂Cl₂	25	1 min	95	5
2	Cu(OTf)₂(1)	CH₂Cl₂	25	1 min	73	6
3	Y(OTf)₃ (1)	CH₂Cl₂	25	0.2 h	93	7
4	Sm(OTf)₃ (1)	CH₂Cl₂	25	0.25 h	88	8
5	Eu(OTf)₃ (1)	CH₂Cl₂	25	0.3 h	89	9
6	Yb(OTf)₃ (1)	CH₂Cl₂	25	0.15 h	93	7
7	Lu(OTf)₃ (1)	CH₂Cl₂	25	0.35 h	94	6
8	Sc(OTf)₃ (5)	CH₂Cl₂	25	1 min	87	13
9	Sc(OTf)₃ (1)	ClCH₂CH₂Cl	25	1 min	98	2
10	Sc(OTf)₃ (1)	DMF	25	24 h	NR	NR
11	Sc(OTf)₃ (1)	DMSO	25	24 h	NR	NR
12	Sc(OTf)₃ (1)	CH₃CN	25	1 min	32	0
13	Sc(OTf)₃ (1)	THF	25	4 h	35	65
14	Sc(OTf)₃ (1)	Toluene	25	1 min	90	6
15	Sc(OTf)₃ (1)	THF	30	2.5 h	11	89
16	Sc(OTf)₃ (1)	THF	35	1.5 h	40	60
17^d	Sc(OTf)₃ (1)	THF	30	9 h	—	88
18^e	Sc(OTf)₃ (0.05)	ClCH₂CH₂Cl	25	16 h	94	4
19^f	Sc(OTf)₃ (0.1)	THF	45	144 h	—	90

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溶剂控制三氟甲烷磺酸钪催化2-(杂)芳基-N-磺酰基吖丁啶开环反应: 烯丙胺/1,3-噁嗪衍生物的合成

Solvent-Controlled Sc(OTf)₃-Catalyzed Ring Opening Reaction of 2-(Hetero)aryl-N-sulfonylazetidines: Synthesis of Allylic Amines/1,3-Oxazinane Derivatives

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