Cross-Dehydrogenative Coupling of Azoles with α-C(sp3)-H of Ethers and Thioethers under Metal-Free Conditions: Functionalization of H-N Azoles via C-H Activation

被引：79

作者：

Aruri, Hariprasad ^{[1
,2
]}

Singh, Umed ^{[1
,2
]}

Sharma, Sumit ^{[1
,2
]}

Gudup, Satish ^{[1
]}

Bhogal, Mukesh ^{[1
]}

Kumar, Sanjay ^{[1
]}

Singh, Deepika ^{[3
]}

Gupta, Vivek K. ^{[4
]}

Kant, Rajni ^{[4
]}

Vishwakarma, Ram A. ^{[1
,2
]}

Singh, Parvinder Pal ^{[1
,2
]}

机构：

[1] CSIR Indian Inst Integrat Med, Div Med Chem, Jammu 18001, India

[2] Acad Sci & Innovat Res, Jammu 18001, India

[3] CSIR Indian Inst Integrat Med, Jammu 18001, India

[4] Univ Jammu, Xray Crystallog Lab, Jammu 180006, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 03期

关键词：

ANTIFUNGAL ACTIVITY; CATALYZED SYNTHESIS; BOND ADJACENT; BENZIMIDAZOLE; ACYLOXYLATION; HETEROCYCLES; ALKYLATION; AMINATION; DESIGN; BENZOTRIAZOLE;

D O I：

10.1021/jo502477r

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A metal-free cross-dehydrogenative coupling method for the synthesis of N-substituted azoles has been developed. The TBAI/TBHP system catalyzed the coupling of azoles with ethers and thioethers via a-C(sp(3))H activation. Under the optimized conditions, a diverse range of un/substituted azoles such as 1H-benzimidazole, 9H-purine, 1H-benzotriazole, 1H-1,2,3-triazole, 1H-1,2,4-triazole, and 1H-pyrazole were successfully employed for coupling with various ethers and thioethers such as tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethyl ether, tetrahydrothiophene, and 1,3-dithiolane.

引用

页码：1929 / 1936

页数：8

共 41 条

[1] Synthesis and antibacterial activity evaluation of metronidazole-triazole conjugates [J].

Beena ;

Kumar, Nitin ;

Rohilla, Rajesh K. ;

Roy, N. ;

Rawat, Diwan S. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (05) :1396-1398

[2] 1-(5-Carboxyindol-1-yl)propan-2-ones as inhibitors of human cytosolic phospholipase A2α: Synthesis and properties of bioisosteric benzimidazole, benzotriazole and indazole analogues [J].

Bovens, Stefanie ;

Kaptur, Martina ;

Elfringhoff, Alwine Schulze ;

Lehr, Matthias .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (08) :2107-2111

[3] Direct Condensation of Sulfonamide and Formamide: Nal-Catalyzed Synthesis of N-Sulfonyl Formamidine Using TBHP as Oxidant [J].

Chen, Shulin ;

Xu, Yuan ;

Wan, Xiaobing .

ORGANIC LETTERS, 2011, 13 (23) :6152-6155

[4] Metal-free oxidative direct C(sp3)-H bond functionalization of ethers with α,α-diaryl allylic alcohols [J].

Chu, Xue-Qiang ;

Meng, Hua ;

Zi, You ;

Xu, Xiao-Ping ;

Ji, Shun-Jun .

CHEMICAL COMMUNICATIONS, 2014, 50 (68) :9718-9721

[5] Antifungal agents.: 11.: N-substituted derivatives of 1-[(aryl)(4-aryl-1H-pyrrol-3-yl)methyl]-1H-imidazole:: Synthesis, anti-Candida activity, and QSAR studies [J].

Di Santo, R ;

Tafi, A ;

Costi, R ;

Botta, M ;

Artico, M ;

Corelli, F ;

Forte, M ;

Caporuscio, F ;

Angiolella, L ;

Palamara, AT .

JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (16) :5140-5153

[6] Conventional and microwave assisted synthesis of 2-oxo-4-substituted aryl-azetidine derivatives of benzotriazole: A new class of biological compounds [J].

Dubey, Adesh ;

Srivastava, S. K. ;

Srivastava, S. D. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2011, 21 (01) :569-573

[7] SYNTHESIS OF (E)-1-(5-CHLOROTHIEN-2-YL)-2-(1H-IMIDAZOL-1-YL)ETHANONE 2,6-DICHLOROPHENYLHYDRAZONE HYDROCHLORIDE, A NOVEL, ORALLY ACTIVE ANTI-FUNGAL AGENT [J].

DYER, RL ;

ELLAMES, GJ ;

HAMILL, BJ ;

MANLEY, PW ;

POPE, AMS .

JOURNAL OF MEDICINAL CHEMISTRY, 1983, 26 (03) :442-445

[8] A Metal-Free Amination of Benzoxazoles - The First Example of an Iodide-Catalyzed Oxidative Amination of Heteroarenes [J].

Froehr, Tanja ;

Sindlinger, Christian P. ;

Kloeckner, Ulrich ;

Finkbeiner, Peter ;

Nachtsheim, Boris J. .

ORGANIC LETTERS, 2011, 13 (14) :3754-3757

[9] Synthesis of diversely fluorinated pyrazoles as novel active agrochemical ingredients [J].

Giornal, Florence ;

Pazenok, Sergiy ;

Rodefeld, Lars ;

Lui, Norbert ;

Vors, Jean-Pierre ;

Leroux, Frederic R. .

JOURNAL OF FLUORINE CHEMISTRY, 2013, 152 :2-11

[10] The Bu4NI-catalyzed alfa-acyloxylation of ketones with benzylic alcohols [J].

Guo, Songjin ;

Yu, Jin-Tao ;

Dai, Qiang ;

Yang, Haitao ;

Cheng, Jiang .

CHEMICAL COMMUNICATIONS, 2014, 50 (47) :6240-6242

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