布朗斯特酸催化合成亚砜亚胺基二氢吡喃酮类衍生物

doi:10.6023/cjoc202108015

摘要/Abstract

亚砜亚胺基团和二氢吡喃酮结构均具有潜在的生物活性, 但目前尚无制备亚砜亚胺基取代的二氢吡喃酮类衍生物的方法. 开发了一种使用磷酸二苯酯作为布朗斯特酸催化剂, 通过亚砜亚胺和二氢吡喃酮的亲核取代反应, 合成亚砜亚胺基取代的二氢吡喃酮类衍生物的新方法, 收率为44%~78%. 该方法条件温和、操作简单且官能团兼容性好, 无需传统方法中使用的贵金属催化剂, 为糖苷类化合物的合成提供了一种新颖高效的策略.

关键词: 布朗斯特酸, 亚砜亚胺, 二氢吡喃酮, 糖苷类化合物

Both sulfoximide and dihydropyranone derivatives have potential bioactivities. However, it is still undisclosed to prepare sulfoximide-substituted dihydropyranone derivatives. Herein, diphenyl phosphate, as Brønsted acid was used to catalyze the nucleophilic substitution reactions of sulfoximides and dihydropyranones to afford sulfoximide substituted dihydropyranone derivatives in 44%~78% yields. This method features mild conditions, simple operation and good functional group compatibility, which avoids using noble metals in traditional manners and provides a novel and effective strategy for the synthesis of glycosides.

Key words: Brønsted acid, sulfoximidie, dihydropyranone, glycoside

引用此文

孙鑫浩, 段学伦, 宋汪泽, 姜文凤. 布朗斯特酸催化合成亚砜亚胺基二氢吡喃酮类衍生物[J]. 有机化学, 2022, 42(2): 487-497.

Xinhao Sun, Xuelun Duan, Wangze Song, Wenfeng Jiang. Brønsted Acid-Catalyzed the Synthesis of Sulfoximide Substituted Dihydropyranone Derivatives[J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 487-497.

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参考文献 25

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Entry	Catalyst (mol%)	Temp./℃	Solvent	Yield^b/%
1^c	[Ir(cod)Cl]₂ (2.5)	r.t.	CHCl₃	0
2^d	Pd(OAc)₂ (5)	r.t.	THF	33
3	(PhO)₂P(O)OH (50)	r.t.	CHCl₃	43
4	HCl (50)	r.t.	CHCl₃	26
5	TsOH (50)	r.t.	CHCl₃	15
6	TfOH (50)	r.t.	CHCl₃	18
7	TFA (50)	r.t.	CHCl₃	25
8	CsA (50)	r.t.	CHCl₃	38
9	PhCOOH (50)	r.t.	CHCl₃	0
10	(PhO)₂P(O)OH (50)	r.t.	DCM	41
11	(PhO)₂P(O)OH (50)	r.t.	DCE	38
12	(PhO)₂P(O)OH (50)	r.t.	Hexane	0
13	(PhO)₂P(O)OH (50)	r.t.	Toluene	33
14	(PhO)₂P(O)OH (50)	r.t.	THF	Trace
15	(PhO)₂P(O)OH (50)	r.t.	Acetone	24
16	(PhO)₂P(O)OH (50)	r.t.	MeCN	20
17	(PhO)₂P(O)OH (50)	r.t.	DMF	0
18	(PhO)₂P(O)OH (20)	r.t.	CHCl₃	43
19	(PhO)₂P(O)OH (10)	r.t.	CHCl₃	38
20^e	(PhO)₂P(O)OH (20)	r.t.	CHCl₃	57
21^f	(PhO)₂P(O)OH (20)	r.t.	CHCl₃	58
22^f^,^g	(PhO)₂P(O)OH (20)	r.t.	CHCl₃	68
23^f^,^h	(PhO)₂P(O)OH (20)	r.t.	CHCl₃	64

Entry	Catalyst (mol%)	Temp./℃	Solvent	Yield^b/%
1^c	[Ir(cod)Cl]₂ (2.5)	r.t.	CHCl₃	0
2^d	Pd(OAc)₂ (5)	r.t.	THF	33
3	(PhO)₂P(O)OH (50)	r.t.	CHCl₃	43
4	HCl (50)	r.t.	CHCl₃	26
5	TsOH (50)	r.t.	CHCl₃	15
6	TfOH (50)	r.t.	CHCl₃	18
7	TFA (50)	r.t.	CHCl₃	25
8	CsA (50)	r.t.	CHCl₃	38
9	PhCOOH (50)	r.t.	CHCl₃	0
10	(PhO)₂P(O)OH (50)	r.t.	DCM	41
11	(PhO)₂P(O)OH (50)	r.t.	DCE	38
12	(PhO)₂P(O)OH (50)	r.t.	Hexane	0
13	(PhO)₂P(O)OH (50)	r.t.	Toluene	33
14	(PhO)₂P(O)OH (50)	r.t.	THF	Trace
15	(PhO)₂P(O)OH (50)	r.t.	Acetone	24
16	(PhO)₂P(O)OH (50)	r.t.	MeCN	20
17	(PhO)₂P(O)OH (50)	r.t.	DMF	0
18	(PhO)₂P(O)OH (20)	r.t.	CHCl₃	43
19	(PhO)₂P(O)OH (10)	r.t.	CHCl₃	38
20^e	(PhO)₂P(O)OH (20)	r.t.	CHCl₃	57
21^f	(PhO)₂P(O)OH (20)	r.t.	CHCl₃	58
22^f^,^g	(PhO)₂P(O)OH (20)	r.t.	CHCl₃	68
23^f^,^h	(PhO)₂P(O)OH (20)	r.t.	CHCl₃	64