Practical Synthesis of Chromeno[ 2,3-b] indole Skeleton via an Aldehyde Group Insertion/Aromatization Strategy

被引：13

作者：

Liu, Jianming ^{[1
]}

Liu, Na ^{[1
]}

Yue, Yuanyuan ^{[1
]}

Wang, Yanyan ^{[1
]}

Chen, Kaige ^{[1
]}

Zhang, Jia ^{[1
]}

Zhao, Shufang ^{[1
]}

Zhuo, Kelei ^{[1
]}

机构：

[1] Henan Normal Univ, Collaborat Innovat Ctr Henan Prov Green Mfg Fine, Henan Key Lab Boron Chem & Adv Energy Mat,Minist, Key Lab Green Chem Media & React,Sch Chem & Chem, Xinxiang 453007, Henan, Peoples R China

来源：

CHEMISTRY-AN ASIAN JOURNAL | 2017年 / 12卷 / 04期

基金：

中国博士后科学基金; 中国国家自然科学基金;

关键词：

aldehydes; cyclization; heterocycles; indoles; palladium; C-O BOND; ULLMANN-TYPE SYNTHESIS; ARYL HALIDES; DIARYL ETHERS; ONE-POT; CROSS-COUPLINGS; CATALYZED ARYLATION; PHENOLS; EFFICIENT; SALICYLALDEHYDES;

D O I：

10.1002/asia.201601681

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The synthesis of chromeno[2,3-b] indole from simple starting materials remains a demanding process. Herein, 2-bromoindole undergoes nucleophilic attack from salicylaldehyde, followed by intramolecular insertion of an aldehyde group and aromatization to generate the desired chromeno[2,3-b] indoles. Moreover, various functional groups were tolerated and a gram-scale synthesis of the product could be achieved under the optimized condition.

引用

页码：401 / 404

页数：4

共 50 条

[31] Synthesis and cytotoxic activity of novel hexahydropyrrolo[2,3-b]indole imidazolium salts
Zhou, Yunjing
Duan, Kunyun
Zhu, Liang
Liu, Zhengfeng
Zhang, Chaobo
Yang, Lijuan
Li, Minyan
Zhang, Hongbin
Yang, Xiaodong
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2016, 26 (02) : 460 - 465
[32] A New and Facile Synthesis of Thieno[2,3-b]indole Derivatives via Condensation of Isocyanide and Indolin-2-thiones
Moghaddam, Firouz Matloubi
Saeidian, Hamdollah
Mirjafary, Zohreh
Taheri, Salman
Kheirjou, Somayyeh
SYNLETT, 2009, (07) : 1047 - 1050
[33] Preparation of Pyrido[2,3-b]indole Derivatives Using Silicates of Group 1 and 2 Metals
Sheikh, Setareh
Fazlinia, Abbas
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2018, 55 (10) : 2291 - 2296
[34] Synthesis of thieno[2,3-b]indole-2,3-diones and their ring expansions induced by diazomethane
Berg, Robert
Bergman, Jan
TETRAHEDRON, 2017, 73 (38) : 5654 - 5658
[35] Construction of Azepino[2,3-b]indole Core via Sulfur Ylide Mediated Annulations
Li, Jun-Long
Dai, Qng-Song
Yang, Kai-Chuan
Liu, Yue
Zhang, Xiang
Leng, Hai-Jun
Peng, Cheng
Huang, Wei
Li, Qing-Zhu
ORGANIC LETTERS, 2018, 20 (23) : 7628 - 7632
[36] Engaging thieno[2,3-b]indole-2,3-dione for the efficient synthesis of spiro[indoline-3,4′-thiopyrano[2,3-b]indole] by reaction withN-substituted isatilidenes
Thomas, Noble V.
Sathi, Vidya
Deepthi, Ani
Sudheendran Leena, Sruthi
Chopra, Sidharth
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2021, 58 (01) : 48 - 55
[37] Dipolar Dyes with a Pyrrolo[2,3-b]quinoxaline Skeleton Containing a Cyano Group and a Bridged Tertiary Amino Group: Synthesis, Solvatofluorochromism, and Bioimaging
Lukasiewicz, Lukasz G.
Deperasinska, Irena
Poronik, Yevgen M.
Jun, Yong Woong
Banasiewicz, Marzena
Kozankiewicz, Boleslaw
Ahn, Kyo Han
Gryko, Daniel T.
CHEMISTRY-AN ASIAN JOURNAL, 2016, 11 (11) : 1718 - 1724
[38] Synthesis and in vitro antiproliferative activity of new 11-aminoalkylamino-substituted chromeno[2,3-b]indoles
Peng, Wei
Switalska, Marta
Wang, Li
Mei, Zhen-Wu
Edazawa, Yoshiki
Pang, Cui-Qing
El-Sayed, Ibrahim El-Tantawy
Wietrzyk, Joanna
Inokuchi, Tsutomu
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2012, 58 : 441 - 451
[39] SYNTHESIS AND PROPERTIES OF 10-ARYL-10-HYDROXY-10H-CHROMENO[2,3-B]PYRIDINES
MIKHALEV, AI
KONSHIN, ME
ZHURNAL ORGANICHESKOI KHIMII, 1977, 13 (05): : 1111 - 1115
[40] Chemoselective asymmetric synthesis of C-3a-(3-hydroxypropyl)tetrahydropyrrolo[2,3-b]indole and C-4a-(2-aminoethyl)tetrahydropyrano[2,3-b]indole derivatives
Pellegrino, Sara
Clerici, Francesca
Contini, Alessandro
Leone, Samantha
Pilati, Tullio
Gelmi, Maria Luisa
TETRAHEDRON, 2009, 65 (10) : 1995 - 2004

← 1 2 3 4 5 →