Regioselective C-H dithiocarbamation of indolizines with tetraalkylthiuram disulfide under metal-free conditions

被引：23

作者：

Liu, Xiang ^{[1
,2
]}

Song, Dan ^{[1
,2
]}

Zhang, Zemin ^{[1
,2
]}

Lin, Jiatong ^{[1
,2
]}

Zhuang, Canzhan ^{[1
,2
]}

Zhan, Haiying ^{[1
,2
]}

Cao, Hua ^{[1
,2
]}

机构：

[1] Guangdong Pharmaceut Univ, Sch Chem & Chem Engn, Zhongshan 528458, Peoples R China

[2] Guangdong Pharmaceut Univ, Guangdong Cosmet Engn & Technol Res Ctr, Zhongshan 528458, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2021年 / 19卷 / 24期

基金：

中国国家自然科学基金;

关键词：

ANTIFUNGAL ACTIVITY; DERIVATIVES; CHEMISTRY; COMPLEXES; CANCER; ESTERS; RUBBER; AGENT;

D O I：

10.1039/d1ob00701g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient and straightforward metal-free regioselective C-H dithiocarbamation of indolizines with tetraalkylthiuram disulfide has been described. A series of indolizine-dithiocarbamate derivatives were easily accessed in moderate to good yields with a broad scope. In addition, imidazo[1,2-a]pyridines were also well tolerated to afford diverse imidazoheterocycle-dithiocarbamate products, which are expected to be utilized for drug discovery. Of note, the reaction could be readily scaled up, and shows its practical value in organic synthesis.

引用

页码：5284 / 5288

页数：5

共 53 条

[1]

Berry DJ, 2012, MINI-REV MED CHEM, V12, P1174

[2] Lung Cancer Chemotherapy, New Treatment and Related Patents [J].

Cheepsattayakorn, Attapon ;

Cheepsattayakorn, Ruangrong .

RECENT PATENTS ON ANTI-CANCER DRUG DISCOVERY, 2014, 9 (03) :372-381

[3] Direct thiocarbamation of imidazoheterocycles via dual C-H sulfurization [J].

Deng, Jian-Chao ;

Zhang, Jun-Rong ;

Li, Ming-Hua ;

Huang, Jie-Cheng ;

Lai, Zhi-Sheng ;

Tong, Xin-Yu ;

Cui, Zi-Ning ;

Tang, Ri-Yuan .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (34) :7854-7857

[4] Metal-free direct thiocarbamation of imidazopyridines with carbamoyl chloride and elemental sulfur [J].

Deng, Jian-Chao ;

Zhuang, Shi-Bin ;

Liu, Quan-Zhu ;

Lin, Zi-Wei ;

Su, Yu-Liang ;

Chen, Jia-Hao ;

Tang, Ri-Yuan .

RSC ADVANCES, 2017, 7 (85) :54013-54016

[5] Synthesis of N,N-diethyldithiocarbamate functionalized 1,4-polyisoprene, from natural rubber and synthetic 1,4-polyisoprene [J].

Derouet, D. ;

Tran, Q. N. ;

Thuc, H. Ha .

EUROPEAN POLYMER JOURNAL, 2007, 43 (05) :1806-1824

[6] Synthesis of Polymer-Grafted Natural Rubbers by Radical Photopolymerization of Vinyl Monomers Initiated from the Rubber Chains [J].

Derouet, D. ;

Tran, Quang Ngoc ;

Thuc, H. Ha .

JOURNAL OF APPLIED POLYMER SCIENCE, 2009, 114 (04) :2149-2160

[7] Copper-Catalyzed C(sp2)-S Coupling Reactions for the Synthesis of Aryl Dithiocarbamates with Thiuram Disulfide Reagents [J].

Dong, Zhi-Bing ;

Liu, Xing ;

Bolm, Carsten .

ORGANIC LETTERS, 2017, 19 (21) :5916-5919

[8] Identification of pyridazino[4,5-b]indolizines as selective PDE4B inhibitors [J].

Donnell, Andrew F. ;

Dollings, Paul J. ;

Butera, John A. ;

Dietrich, Arlene J. ;

Lipinski, Kerri K. ;

Ghavami, Afshin ;

Hirst, Warren D. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (07) :2163-2167

[9] Convenient and efficient synthesis of functionalized unsymmetrical alkynyl sulfides [J].

Doroszuk, J. ;

Musiejuk, M. ;

Demkowicz, S. ;

Rachon, J. ;

Witt, D. .

RSC ADVANCES, 2016, 6 (107) :105449-105453

[10] Generation of ArS- and ArSe-Substituted 4-Quinolone Derivatives Using Sodium Iodide As an Inducer [J].

Ghosh, Prasanjit ;

Nandi, Aritra Kumar ;

Chhetri, Gautam ;

Das, Sajal .

JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (20) :12411-12419

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