A facile access to thieno[2,3-b]indoles via sulfur-mediated decarboxylative cyclization of α, β-unsaturated carboxylic acids with indoles

被引：11
|
作者：
Zhang, Hao-Lin [1 ]
Wen, Fei [1 ]
Sheng, Wen-Bing [1 ]
Yin, Peng [4 ]
Zhang, Chun-Tao [1 ]
Peng, Cai-Yun [1 ]
Peng, Dong-Ming [1 ]
Liao, Duan-Fang [1 ,2 ]
Fu, Rong-Geng [1 ,2 ,3 ]
机构：
[1] Hunan Univ Chinese Med, Sch Pharm, Changsha 410208, Hunan, Peoples R China
[2] Hunan Univ Chinese Med, Key Lab Qual Evaluat Bulk Herbs Hunan Prov, Changsha 410208, Hunan, Peoples R China
[3] Hunan Key Lab Druggabil & Preparat Modificat Trad, Changsha 410208, Hunan, Peoples R China
[4] Hunan Normal Univ, Coll Chem & Chem Engn, Minist Educ, Key Lab Chem Biol & Tradit Chinese Med Res, Changsha 410081, Hunan, Peoples R China
来源：
TETRAHEDRON LETTERS | 2019年 / 60卷 / 01期
关键词：
Thieno[2,3-b]indoles; Sulfur-mediated; Decarboxylation; Cyclization; Three-component reaction; FUNCTIONALIZATION; THIOAMIDATION; AMINATION;
D O I：
10.1016/j.tetlet.2018.11.062
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient synthesis of thieno[2,3-b]indoles via a one-pot three-component reaction was well established. By using inexpensive and commercial available indoles and a, a-unsaturated carboxylic acids in the presence of elemental sulfur, various functional groups were achieved in moderate to good yields. (C) 2018 Elsevier Ltd. All rights reserved.
引用
收藏
页码：80 / 83
页数：4
相关论文
共 50 条
  • [31] THE UTILIZATION OF ALPHA,BETA-UNSATURATED ACIDS AS MICHAEL ACCEPTORS FOR THE SYNTHESIS OF THIENO[2,3-B]THIOPYRANS
    PONTICELLO, GS
    FREEDMAN, MB
    HOLLOWAY, MK
    AMATO, JS
    CONN, RS
    BALDWIN, JJ
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1987, 194 : 281 - ORGN
  • [32] Synthesis of Dihydrochromeno[2,3-b]indoles via an Fe(OTf)3-Catalyzed Cascade Reaction
    Xiao, Xi
    Lu, Xiaobiao
    Zhang, Ming
    Hou, Haoqing
    Wan, Changfeng
    Liu, Jinbiao
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (23): : 16795 - 16805
  • [33] Sequential Electrophilic Trifluoromethanesulfanylation-Cyclization of Tryptamine Derivatives: Synthesis of C(3)-Trifluoromethanesulfanylated Hexahydropyrrolo[2,3-b]indoles
    Yang, Yi
    Jiang, Xueliang
    Qing, Feng-Ling
    JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (17): : 7538 - 7547
  • [34] A cascade deprotonation/intramolecular aldol reaction of α-carbonyl sulfonium ylides with 2-mercaptoindole-3-carbaldehydes and 2-mercaptobenzaldehydes to access thieno[2,3-b]indoles and benzothiophenes
    Yang, Lei
    Zhou, Shun
    Zhao, Jian-Qiang
    You, Yong
    Wang, Zhen-Hua
    Zhou, Ming-Qiang
    Yuan, Wei-Cheng
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (16) : 3678 - 3686
  • [35] Facile preparation of benzo[4,5]thieno[2,3-b]pyridines and naphtho[b-4,5]thieno[2,3-b]pyridines via the reaction of Barton esters and benzynes
    Rao, UN
    Biehl, E
    JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (10): : 3409 - 3411
  • [36] Bronsted-Acid-Mediated Divergent Reactions of Betti Bases with Indoles: An Approach to Chromeno[2,3-b]indoles through Intramolecular Dehydrogenative C2-Alkoxylation of Indole
    Deb, Mohit L.
    Pegu, Choitanya Dev
    Deka, Bhaskar
    Dutta, Prantu
    Kotmale, Amol S.
    Baruah, Pranjal K.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (20) : 3441 - 3448
  • [37] Cobalt(II)/silver relay catalytic isocyanide insertion/cycloaddition cascades: a new access to pyrrolo[2,3-b]indoles
    Gao, Qian
    Zhou, Peng
    Liu, Feng
    Hao, Wen-Juan
    Yao, Changsheng
    Jiang, Bo
    Tu, Shu-Jiang
    CHEMICAL COMMUNICATIONS, 2015, 51 (46) : 9519 - 9522
  • [38] Facile synthesis of some novel pyrido[3′,2′:4,5]thieno[2,3-b][1,4]thiazine-8-carboxylic acids
    Al-Huniti, Mohammed H.
    EI-Abadelah, Mustafa M.
    Zahra, Jalal A.
    Sabri, Salim S.
    Ingendoh, Arnd
    MOLECULES, 2007, 12 (03): : 497 - 503
  • [39] 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
  • [40] Synthesis of diversely functionalized hexahydropyrrolo[2,3-b]indoles using domino reactions, olefination, isomerization and Claisen rearrangement followed by reductive cyclization
    Kawasaki, T
    Ogawa, A
    Terashima, R
    Saheki, T
    Ban, N
    Sekiguchi, H
    Sakaguchi, K
    Sakamoto, M
    JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (08): : 2957 - 2966
12345