Metal-Free [2+2+2] Cycloaddition of Ynamide-Nitriles with Ynamides: A Highly Regio- and Chemoselective Synthesis of δ-Carboline Derivatives

被引:25
作者
Wen, Hao [1 ]
Cao, Wei [1 ]
Liu, Yu [1 ]
Wang, Liang [3 ]
Chen, Ping [1 ]
Tang, Yu [1 ,2 ]
机构
[1] Ocean Univ China, Chinese Minist Educ, Key Lab Marine Drugs, Sch Med & Pharm, Yushan Rd, Qingdao 266003, Peoples R China
[2] Qingdao Natl Lab Marine Sci & Technol, Lab Marine Drugs & Bioprod, Qingdao 266237, Peoples R China
[3] Qingdao Agr Univ, Coll Chem & Pharmaceut Sci, Qingdao 266109, Peoples R China
基金
中国国家自然科学基金;
关键词
FORMAL 3+2 CYCLOADDITION; SUBSTITUTED PYRIDINES; EFFICIENT SYNTHESIS; DRUG DISCOVERY; HOST MATERIALS; ALPHA; INHIBITORS; BETA; NITROGEN; ACCESS;
D O I
10.1021/acs.joc.8b02112
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A metal-free formal [2 + 2 + 2] cycloaddition of functionalized ynamide-nitriles with ynamides is disclosed which offers highly efficient access to polysubstituted delta-carboline derivatives under the mediation of TfOH. This strategy is highly regioselective and chemoselective and displays mild conditions, high yields, and efficiency (within 1 min) in addition to substrates scopes (56 examples).
引用
收藏
页码:13308 / 13324
页数:17
相关论文
共 59 条
[1]   New synthesis of benzo-δ-carbolines, cryptolepines, and their salts:: In vitro cytotoxic, antiplasmodial, and antitrypanosomal activities of δ-caribolines, benzo-δ-carbolines, and cryptolepines [J].
Arzel, E ;
Rocca, P ;
Grellier, P ;
Labaeïd, M ;
Frappier, F ;
Guéritte, F ;
Gaspard, C ;
Marsais, F ;
Godard, A ;
Quéguiner, G .
JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (06) :949-960
[2]   Preparation of azaindolines and benzoyl substituted azaindolines: precursors of triazabenzo[cd]azulen-9-one PDE4 inhibitors [J].
Badland, Matthew ;
Devillers, Ingrid ;
Durand, Corinne ;
Fasquelle, Veronique ;
Gaudilliere, Bernard ;
Jacobelli, Henry ;
Manage, Ajith C. ;
Pevet, Isabelle ;
Puaud, Jocelyne ;
Shorter, Anthony J. ;
Wrigglesworth, Roger .
TETRAHEDRON LETTERS, 2011, 52 (41) :5292-5296
[3]   The use of isolated natural products as scaffolds for the generation of chemically diverse screening libraries for drug discovery [J].
Barnes, Emma C. ;
Kumar, Rohitesh ;
Davis, Rohan A. .
NATURAL PRODUCT REPORTS, 2016, 33 (03) :372-381
[4]   Neocryptolepine (Cryprotackieine), A Unique Bioactive Natural Product: Isolation, Synthesis, and Profile of Its Biological Activity [J].
Bracca, Andrea B. J. ;
Heredia, Daniel A. ;
Larghi, Enrique L. ;
Kaufman, Teodoro S. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (36) :7979-8003
[5]   Synthesis, structure-activity relationships, and pharmacological profile of 9-amino-4-oxo-1-phenyl-3,4,6,7-tetrahydro[1,4]diazepino[6,7,1-hi]indoles:: Discovery of potent, selective phosphodiesterase type 4 inhibitors [J].
Burnouf, C ;
Auclair, E ;
Avenel, N ;
Bertin, B ;
Bigot, C ;
Calvet, A ;
Chan, K ;
Durand, C ;
Fasquelle, V ;
Féru, F ;
Gilbertsen, R ;
Jacobelli, H ;
Kebsi, A ;
Lallier, E ;
Maignel, J ;
Martin, B ;
Milano, S ;
Ouagued, M ;
Pascal, Y ;
Pruniaux, MP ;
Puaud, J ;
Rocher, MN ;
Terrasse, C ;
Wrigglesworth, R ;
Doherty, AM .
JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (25) :4850-4867
[6]   Synthesis of δ-Carbolines via a Pd-Catalyzed Sequential Reaction from 2-Iodoanilines and N-Tosyl-enynamines [J].
Cao, Jian ;
Xu, Yongping ;
Kong, Long ;
Cui, Yuming ;
Hu, Ziqiang ;
Wang, Guanhai ;
Deng, Yuan ;
Lai, Guoqiao .
ORGANIC LETTERS, 2012, 14 (01) :38-41
[7]   A Highly Regio- and Stereoselective Syntheses of α-Halo Enamides, Vinyl Thioethers, and Vinyl Ethers with Aqueous Hydrogen Halide in Two-Phase Systems [J].
Cao, Wei ;
Chen, Ping ;
Wang, Liang ;
Wen, Hao ;
Liu, Yu ;
Wang, Wanshu ;
Tang, Yu .
ORGANIC LETTERS, 2018, 20 (15) :4507-4511
[8]   Visible-Light-Induced Synthesis of Carbazoles by in Situ Formation of Photosensitizing Intermediate [J].
Chatterjee, Tanmay ;
Roh, Geum-bee ;
Shoaib, Mahbubul Alam ;
Suh, Chang-Heon ;
Kim, Jun Soo ;
Cho, Cheon-Gyu ;
Cho, Eun Jin .
ORGANIC LETTERS, 2017, 19 (07) :1906-1909
[9]   1,4-Azaindole, a Potential Drug Candidate for Treatment of Tuberculosis [J].
Chatterji, Monalisa ;
Shandil, Radha ;
Manjunatha, M. R. ;
Solapure, Suresh ;
Ramachandran, Vasanthi ;
Kumar, Naveen ;
Saralaya, Ramanatha ;
Panduga, Vijender ;
Reddy, Jitendar ;
Prabhakar, K. R. ;
Sharma, Sreevalli ;
Sadler, Claire ;
Cooper, Christopher B. ;
Mdluli, Khisi ;
Iyer, Pravin S. ;
Narayanan, Shridhar ;
Shirude, Pravin S. .
ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 2014, 58 (09) :5325-5331
[10]   TfOH-mediated [2+2+2] cycloadditions of ynamides with two discrete nitriles: synthesis of 4-aminopyrimidine derivatives [J].
Chen, Ping ;
Song, Cai-xia ;
Wang, Wan-shu ;
Yu, Xue-liang ;
Tang, Yu .
RSC ADVANCES, 2016, 6 (83) :80055-80058