Selectfluor氧化合成2-芳基苯并噻唑的新方法

doi:10.6023/cjoc202105010

摘要/Abstract

开发了一种以芳基甲基酮或脂肪酮和2-氨基苯硫酚为原料, 正丁醇为溶剂, 120 ℃条件下经Selectfluor氧化合成2-取代苯并噻唑类衍生物的方法. 通过改变底物芳基甲基酮上的取代基可以获得具有生物活性的药物中间体.

关键词: 选择性氟试剂, 2-芳基苯并噻唑, 芳基甲基酮, 2-氨基苯硫酚, 氧化

2-Arylbenzothiazoles were effectively synthesized via an oxidative process by Selectfluor in 1-butanol at 120 ℃, using 2-arylbenzothiazoles and aryl/aliphatic ketones as starting materials. Bioactive pharmaceutical intermediates were obtained by selecting substituents on the ring of aryl methyl ketones.

Key words: Selectfluor, 2-arylbenzothiazole, aryl methyl ketone, 2-aminobenzenethiol, oxidation

引用此文

傅琴姣, 张瑞芹, 裘浣沂, 马仁超, 马永敏. Selectfluor氧化合成2-芳基苯并噻唑的新方法[J]. 有机化学, 2021, 41(9): 3585-3592.

Qinjiao Fu, Ruiqin Zhang, Huanyi Qiu, Renchao Ma, Yongmin Ma. A New Method for the Synthesis of 2-Arylbenzothiazoles Oxidized by Selectfluor[J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3585-3592.

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Entry	Product	Ar	R¹	Yield/%
1	3aa	C₆H₅	H	75 (72^b)
2	3ba	2-MeOC₆H₄	H	75
3	3ca	2-ClC₆H₄	H	73
4	3da	3-MeOC₆H₄	H	68
5	3ea	3-ClC₆H₄	H	60
6	3fa	4-ClC₆H₄	H	62
7	3ga	4-CH₃C₆H₄	H	78
8	3ha	4-NH₂C₆H₄	H	73
9	3ia	3,5-(CH₃O)₂C₆H₃	H	73
10	3ja	3,4-(CH₃)₂C₆H₃	H	76
11	3ka	3,5-F₂C₆H₃	H	70
12	3la	2,4-(CH₃)₂C₆H₃	H	65
13	3ma	3-MeO-4-HO-C₆H₃	H	56
14	3na	4-O₂NC₆H₄	H	0
15	3oa	2-Thienyl	H	58
16	3pa	2-Benzothienyl	H	55
17	3qa	2-Benzofuryl	H	40
18	3ra	2-Naphthyl	H	60
19	3sa	4-CF₃C₆H₄	H	74
20	3ab	C₆H₅	5-Cl	79
21	3eb	4-FC₆H₄	5-Cl	75
22	3fb	4-MeOC₆H₄	5-Cl	66
23	3kb	3,5-F₂C₆H₃	5-Cl	78
24	3lb	2,4-(CH₃)₂C₆H₃	5-Cl	70
25	3mb	3-MeO-4-HO-C₆H₃	5-Cl	67

Entry	Product	Ar	R¹	Yield/%
1	3aa	C₆H₅	H	75 (72^b)
2	3ba	2-MeOC₆H₄	H	75
3	3ca	2-ClC₆H₄	H	73
4	3da	3-MeOC₆H₄	H	68
5	3ea	3-ClC₆H₄	H	60
6	3fa	4-ClC₆H₄	H	62
7	3ga	4-CH₃C₆H₄	H	78
8	3ha	4-NH₂C₆H₄	H	73
9	3ia	3,5-(CH₃O)₂C₆H₃	H	73
10	3ja	3,4-(CH₃)₂C₆H₃	H	76
11	3ka	3,5-F₂C₆H₃	H	70
12	3la	2,4-(CH₃)₂C₆H₃	H	65
13	3ma	3-MeO-4-HO-C₆H₃	H	56
14	3na	4-O₂NC₆H₄	H	0
15	3oa	2-Thienyl	H	58
16	3pa	2-Benzothienyl	H	55
17	3qa	2-Benzofuryl	H	40
18	3ra	2-Naphthyl	H	60
19	3sa	4-CF₃C₆H₄	H	74
20	3ab	C₆H₅	5-Cl	79
21	3eb	4-FC₆H₄	5-Cl	75
22	3fb	4-MeOC₆H₄	5-Cl	66
23	3kb	3,5-F₂C₆H₃	5-Cl	78
24	3lb	2,4-(CH₃)₂C₆H₃	5-Cl	70
25	3mb	3-MeO-4-HO-C₆H₃	5-Cl	67