Heterocyclic Iodoniums for the Assembly of Oxygen-Bridged Polycyclic Heteroarenes with Water as the Oxygen Source

被引：49

作者：

Zhu, Daqian ^{[1
,2
]}

Wu, Zhouming ^{[1
]}

Luo, Bingling ^{[1
]}

Du, Yongliang ^{[1
]}

Liu, Panpan ^{[1
]}

Chen, Yunyun ^{[2
]}

Hu, Yumin ^{[1
]}

Huang, Peng ^{[1
]}

Wen, Shijun ^{[1
,2
]}

机构：

[1] Sun Yat Sen Univ, Collaborat Innovat Ctr Canc Med, State Key Lab Oncol South China, Canc Ctr, 651 Dongfeng East Rd, Guangzhou 510060, Peoples R China

[2] Sun Yat Sen Univ, Sch Pharmaceut Sci, 132 Waihuan East Rd, Guangzhou 510006, Guangdong, Peoples R China

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 16期

基金：

中国国家自然科学基金;

关键词：

CYCLIC DIARYLIODONIUM; CATALYZED SYNTHESIS; CONSTRUCTION; CARBAZOLES; REACTIVITY; ARYLATION; INSERTION; STRATEGY; SKELETON; SULFIDE;

D O I：

10.1021/acs.orglett.8b01969

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A diverse set of novel heterocyclic iodoniums was synthesized for the first time. The reactions of these unique iodoniums with environmentally benign water as the oxygen source provided structurally complex oxygen-incorporated heteropolycycles that are essential motifs in natural products and biologically active compounds. The transformation only required low-cost copper acetate. Further derivatization of the obtained polycycles expanded the structural diversity, which is important in the building of chemical libraries for drug discovery.

引用

收藏

页码：4815 / 4818

页数：4

相关论文

共 39 条

[1] NOVEL, POTENT, AND SELECTIVE 5-HT3 RECEPTOR ANTAGONISTS BASED ON THE ARYLPIPERAZINE SKELETON - SYNTHESIS, STRUCTURE, BIOLOGICAL-ACTIVITY, AND COMPARATIVE MOLECULAR-FIELD ANALYSIS STUDIES [J].

ANZINI, M ;

CAPPELLI, A ;

VOMERO, S ;

GIORGI, G ;

LANGER, T ;

HAMON, M ;

MERAHI, N ;

EMERIT, BM ;

CAGNOTTO, A ;

SKORUPSKA, M ;

MENNINI, T ;

PINTO, JC .

JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (14) :2692-2704

[2] Biological importance of structurally diversified chromenes [J].

Costa, Marta ;

Dias, Tatiana A. ;

Brito, Alexandra ;

Proenca, Fernanda .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2016, 123 :487-507

[3] Twenty years on: the impact of fragments on drug discovery [J].

Erlanson, Daniel A. ;

Fesik, Stephen W. ;

Hubbard, Roderick E. ;

Jahnke, Wolfgang ;

Jhoti, Harren .

NATURE REVIEWS DRUG DISCOVERY, 2016, 15 (09) :605-619

[4] SYNTHESIS OF 2-IODO-2'-METHOXYBIPHENYL - A NEW ROUTE TO ORTHO-TERPHENYLS [J].

FUSON, RC ;

ALBRIGHT, RL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (02) :487-490

[5] Potassium tert-Butoxide-Catalyzed Synthesis of Benzofuroazepines via Cyclization of (2-Alkynylbenzyl)oxy Nitriles [J].

Gai, Rafaela ;

Back, Davi F. ;

Zeni, Gilson .

JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (20) :10278-10287

[6] Synthesis, Stereochemistry, Structural Classification, and Chemical Reactivity of Natural Pterocarpans [J].

Goel, Atul ;

Kumar, Amit ;

Raghuvanshi, Ashutosh .

CHEMICAL REVIEWS, 2013, 113 (03) :1614-1640

[7] Metal- Catalyzed Annulation Reactions for p- Conjugated Polycycles [J].

Jin, Tienan ;

Zhao, Jian ;

Asao, Naoki ;

Yamamoto, Yoshinori .

CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (13) :3554-3576

[8] Construction of Bisbenzofuro[2,3-b:3',2'-e]pyridines by Palladium-Catalyzed Double Intramolecular Oxidative C-H/C-H Coupling [J].

Kaida, Hiroyuki ;

Goya, Tsuyoshi ;

Nishi, Yuji ;

Hirano, Koji ;

Satoh, Tetsuya ;

Miura, Masahiro .

ORGANIC LETTERS, 2017, 19 (05) :1236-1239

[9] Tandem Approach to Benzothieno- and Benzofuropyridines from o-Alkynyl Aldehydes via Silver-Catalyzed 6-endo-dig Ring Closure [J].

Kumar, Sonu ;

Cruz-Hernandez, Carlos ;

Pal, Shilpi ;

Saunthwal, Rakesh K. ;

Patel, Monika ;

Tiwari, Rakesh K. ;

Juaristi, Eusebio ;

Verma, Akhilesh K. .

JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (21) :10548-10560

[10] A Series of Novel Terpyridine-Skeleton Molecule Derivants Inhibit Tumor Growth and Metastasis by Targeting Topoisomerases [J].

Kwon, Han-Byeol ;

Park, Chanmi ;

Jeon, Kyung-Hwa ;

Lee, Eunyoung ;

Park, So-Eun ;

Jun, Kyu-Yeon ;

Kadaya, Tara Man ;

Thapa, Pritam ;

Karki, Radha ;

Na, Younghwa ;

Park, Mi Sun ;

Rho, Seung Bae ;

Lee, Eung-Seok ;

Kwon, Youngjoo .

JOURNAL OF MEDICINAL CHEMISTRY, 2015, 58 (03) :1100-1122

← 1 2 3 4 →