Metal- and Solvent-Free Synthesis ofTetrahydrobenzo[c]carbazolones through NaI-Catalyzed Formal [4+2] Annulation

被引:5
作者
Fang, Fang [1 ,2 ]
Zheng, Haolin [1 ]
Mao, Guojiang [3 ]
Chen, Shanping [1 ]
Deng, Guo-Jun [1 ]
机构
[1] Xiangtan Univ, Coll Chem,Minist Educ, Key Lab Environmentally Friendly Chem & Applicat, Key Lab Green Organ Synth & Applicat Hunan Prov, Xiangtan 411105, Peoples R China
[2] Hunan City Univ, Coll Mat & Chem Engn, Yiyang 413000, Peoples R China
[3] Henan Normal Univ, Sch Chem & Chem Engn, Xinxiang 453007, Henan, Peoples R China
基金
中国国家自然科学基金;
关键词
C-H ACTIVATION; ONE-POT SYNTHESIS; FUNCTIONALIZED CARBAZOLES; SUBSTITUTED CARBAZOLES; FACILE ACCESS; INDOLES; ACID; EFFICIENT; ALKYNES; CYCLIZATION;
D O I
10.1021/acs.joc.2c00315
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel strategy for the preparation of functionalcarbazoles through NaI-catalyzed formal [4 + 2] annulation of 2-(indol-3-yl)cyclohexanones and alkynes/alkenes has been devel-oped. The present approach started from easily available rawmaterials and provided a variety of tetrahydrobenzo[c]carbazolonesin satisfactory yields under metal- and solvent-free conditions.Furthermore, the products could be further transformed intostructurally valuable carbazole-based conjugated derivatives
引用
收藏
页码:6052 / 6063
页数:12
相关论文
共 74 条
[1]   Instant Low-Temperature Cross-Linking of Poly(N-vinylcarbazole) for Solution-Processed Multilayer Blue Phosphorescent Organic Light-Emitting Devices [J].
Aizawa, Naoya ;
Pu, Yong-Jin ;
Chiba, Takayuki ;
Kawata, So ;
Sasabe, Hisahiro ;
Kido, Junji .
ADVANCED MATERIALS, 2014, 26 (45) :7543-7546
[2]  
[Anonymous], 1908, J PRAKT CHEM, V77, P403
[3]   Preparation of vinylogous 2-sulfonylindolines by the palladium-catalyzed heteroannulation of o-iodoanilines with dienyl sulfones and their further transformation to indoles and carbazoles [J].
Back, TG ;
Bethell, RJ ;
Parvez, M ;
Taylor, JA .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (25) :8599-8605
[4]   Anti-tuberculosis activity and structure-activity relationships of oxygenated tricyclic carbazole alkaloids and synthetic derivatives [J].
Boerger, Carsten ;
Bruetting, Christian ;
Julich-Gruner, Konstanze K. ;
Hesse, Ronny ;
Kumar, V. Pavan ;
Kutz, Sebastian K. ;
Roennefahrt, Marika ;
Thomas, Claudia ;
Wan, Baojie ;
Franzblau, Scott G. ;
Knoelker, Hans-Joachim .
BIOORGANIC & MEDICINAL CHEMISTRY, 2017, 25 (22) :6167-6174
[5]   Novel approach to biscarbazole alkaloids via Ullmann coupling - synthesis of murrastifoline-A and bismurrayafoline-A [J].
Boerger, Carsten ;
Kataeva, Olga ;
Knoelker, Hans-Joachim .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (36) :7269-7273
[6]   REACTIVITY OF ORGANOPHOSPHORUS COMPOUNDS .19. REDUCTION OF NITRO-COMPOUNDS BY TRIETHYL PHOSPHITE - A CONVENIENT NEW ROUTE TO CARBAZOLES INDOLES INDAZOLES TRIAZOLES AND RELATED COMPOUNDS [J].
CADOGAN, JIG ;
CAMERONW.M ;
MACKIE, RK ;
SEARLE, RJG .
JOURNAL OF THE CHEMICAL SOCIETY, 1965, (SEP) :4831-&
[7]   Transition-metal free 2-arylbenzoxazole formation from aryl amides and cyclohexanones [J].
Cao, Xiangxiang ;
Cheng, Xiufang ;
Bai, Yang ;
Liu, Saiwen ;
Deng, Guo-Jun .
GREEN CHEMISTRY, 2014, 16 (11) :4644-4648
[8]   Development of a Unique Class of Spiro-Type Two-Photon Functional Fluorescent Dyes and Their Applications for Sensing and Bioimaging [J].
Chen, Hua ;
Shang, Huiming ;
Liu, Yong ;
Guo, Rui ;
Lin, Weiying .
ADVANCED FUNCTIONAL MATERIALS, 2016, 26 (44) :8128-8136
[9]   Four-Component Approach to N-Substituted Phenothiazines under Transition-Metal-Free Conditions [J].
Chen, Jinjin ;
Li, Guozheng ;
Xie, Yanjun ;
Liao, Yunfeng ;
Xiao, Fuhong ;
Deng, Guo-Jun .
ORGANIC LETTERS, 2015, 17 (23) :5870-5873
[10]  
Chen P. Y., GREEN SYNTH CATAL, V2021, P78