Practical Synthesis of N -Anilinylphenothiazines Using a Cyclic Hypervalent Iodine Coupling Reagent

被引：0

作者：

Yanase, Kana ^{[1
]}

Morimoto, Koji ^{[1
,2
]}

Dohi, Toshifumi ^{[1
,2
]}

Kita, Yasuyuki ^{[2
]}

机构：

[1] Ritsumeikan Univ, Coll Pharmaceut Sci, 1-1-1 Nojihigashi, Kusatsu, Shiga 5258577, Japan

[2] Ritsumeikan Univ, Res Org Sci & Technol, 1-1-1 Nojihigashi, Kusatsu, Shiga 5258577, Japan

来源：

SYNTHESIS-STUTTGART | 2025年 / 57卷 / 04期

关键词：

hypervalent iodine(III) reagent; aryl C-H amination; solid-liquid separation; coupling reaction; N; -anilinylphenothiazines;

D O I：

10.1055/a-2383-0958

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An improved protocol for the synthesis of N-anilinylphenothiazines based on the coupling reaction of anilines with phenothiazines using cyclic iodine(III) reagent is presented. In the improved method, the product can be isolated and purified without using column chromatography, and the cyclic hypervalent iodine reagent can be quantitatively recovered by aliquot manipulation. The workup procedure presented here is simpler compared to previously reported ones, facilitating large-scale synthesis. The para -selective phenothiazination of nitrogen-containing heterocycles such as hydroquinoline, which is important in pharmacology, was also successfully performed.

引用

页码：748 / 753

页数：6

共 20 条

[1] Oxidative Biaryl Coupling of N-Aryl Anilines by Using a Hypervalent Iodine(III) Reagent [J].

Morimoto, Koji ;

Koseki, Doichi ;

Dohi, Toshifumi ;

Kita, Yasuyuki .

SYNLETT, 2017, 28 (20) :2941-2945

[2] Three-component direct synthesis of substituted pyrroles from easily accessible chemical moieties using hypervalent iodine reagent [J].

Jadhav, Nikhil C. ;

Jagadhane, Prashant B. ;

Patile, Hemlata V. ;

Telvekar, Vikas N. .

TETRAHEDRON LETTERS, 2013, 54 (23) :3019-3021

[3] Operationally Simple Synthesis of N,N-Diethyl-3-methylbenzamide (DEET) Using COMU as a Coupling Reagent [J].

Withey, Jonathan M. ;

Bajic, Andrea .

JOURNAL OF CHEMICAL EDUCATION, 2015, 92 (01) :175-178

[4] SYNTHESIS OF OLIGOSACCHARIDES WITH OLIGOETHYLENE GLYCOL SPACERS AND THEIR CONVERSION INTO GLYCOCONJUGATES USING N,N,N',N''-TETRAMETHYL(SUCCINIMIDO)URONIUM TETRAFLUOROBORATE AS COUPLING REAGENT [J].

ANDERSSON, M ;

OSCARSON, S ;

OBERG, L .

GLYCOCONJUGATE JOURNAL, 1993, 10 (03) :197-201

[5] Perfluoroalkylation of Aryl-N,N-dimethyl Hydrazones Using Hypervalent Iodine(III) Reagents or Perfluoroalkyl Iodides [J].

Janhsen, Benjamin ;

Studer, Armido .

JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (22) :11703-11710

[6] Synthesis of N-acyl-benzotriazole using Mukaiyama reagent [J].

Pandey, Rajesh K. ;

Gupta, Monika ;

Rajput, Chatrasal S. ;

Singh, Anoop S. .

ARKIVOC, 2023,

[7] Synthesis of O-Aroyl-N,N-dimethylhydroxylamines through Hypervalent Iodine-Mediated Amination of Carboxylic Acids with N,N-Dimethylformamide [J].

Zhang, Chuancheng ;

Yue, Qiang ;

Xiao, Zhen ;

Wang, Xianglan ;

Zhang, Qian ;

Li, Dong .

SYNTHESIS-STUTTGART, 2017, 49 (18) :4303-4308

[8] SYNTHESIS OF OLIGOSACCHARIDES WITH OLIGOETHYLENE GLYCOL SPACERS AND THEIR CONVERSION INTO GLYCOCONJUGATES USING N,N,N',N'-TETRAMETHYL(SUCCINIMIDO)URONIUM TETRAFLUOROBORATE AS COUPLING REAGENT (VOL 10, PG 197, 1993) [J].

ANDERSSON, M ;

OSCARSON, S ;

OHBERG, L .

GLYCOCONJUGATE JOURNAL, 1993, 10 (06) :461-465

[9] The efficient direct synthesis of N,O-Acetal compounds as key intermediates of discorhabdin A:: Oxidative fragmentation reaction of α-amino acids or β-amino alcohols by using hypervalent iodine(III) reagents [J].

Harayama, Yu ;

Yoshida, Masako ;

Kamimura, Daigo ;

Wada, Yasufumi ;

Kita, Yasuyuki .

CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (18) :4893-4899

[10] Efficient synthesis of chlorinated Dihydronaphthalene derivatives using N, N-diisopropylformamide-POCl3 as a Vilsmeier reagent [J].

Li, Dinghao ;

Li, Junwei ;

Zhang, Yumeng ;

Zhang, Fang-Lin .

TETRAHEDRON LETTERS, 2025, 169

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