A facile synthesis of 2H-indazoles under neat conditions and further transformation into aza-γ-carboline alkaloid analogues in a tandem one-pot fashion

被引:38
作者
Vidyacharan, Shinde [1 ]
Sagar, A. [1 ]
Chaitra, N. C. [1 ]
Sharada, Duddu S. [1 ]
机构
[1] Indian Inst Technol, Dept Chem, Yeddumailaram 502205, Telangana, India
关键词
SOLID-PHASE SYNTHESIS; N BOND FORMATION; C-N; HETEROCYCLIC-COMPOUNDS; DOMINO REACTION; SOLVENT-FREE; INDAZOLES; DERIVATIVES; ACID; ISOCRYPTOLEPINE;
D O I
10.1039/c4ra06838f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We have described a facile, microwave-assisted, catalyst-free and solvent-free approach to 2H-indazoles and further developed a robust tandem one-pot metal-free strategy for C-C bond formation at the C-3 position of 2H-indazoles leading to a unique class of aza-gamma-carboline alkaloid analogues. This straightforward expedient synthesis constitutes an interesting alternative to the existing conventional transition metal catalyzed reactions.
引用
收藏
页码:34232 / 34236
页数:5
相关论文
共 75 条
[21]   Synthesis of 2H-Indazoles by the [3+2] Dipolar Cycloaddition of Sydnones with Arynes [J].
Fang, Yuesi ;
Wu, Chunrui ;
Larock, Richard C. ;
Shi, Feng .
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (21) :8840-8851
[22]   N-phenylation of azole derivatives by triphenylbismuth derivatives cupric acetate [J].
Fedorov, AY ;
Finet, JP .
TETRAHEDRON LETTERS, 1999, 40 (14) :2747-2748
[23]  
Frank W., 2014, PCT Int. Appl, Patent No. [WO 2014040373 A1 20140320, 2014040373, WO 2014040373 A1]
[24]   2-substituted indazoles from electrogenerated ortho-nitrosobenzylamines. [J].
Frontana-Uribe, BA ;
Moinet, C .
TETRAHEDRON, 1998, 54 (13) :3197-3206
[25]   Solvent-Free and Catalysts-Free Chemistry: A Benign Pathway to Sustainability [J].
Gawande, Manoj B. ;
Bonifacio, Vasco D. B. ;
Luque, Rafael ;
Branco, Paula S. ;
Varma, Rajender S. .
CHEMSUSCHEM, 2014, 7 (01) :24-44
[26]   Benign by design: catalyst-free in-water, on-water green chemical methodologies in organic synthesis [J].
Gawande, Manoj B. ;
Bonifacio, Vasco D. B. ;
Luque, Rafael ;
Branco, Paula S. ;
Varma, Rajender S. .
CHEMICAL SOCIETY REVIEWS, 2013, 42 (12) :5522-5551
[27]   Regioselective Synthesis of 2H-Indazoles Using a Mild, One-Pot Condensation-Cadogan Reductive Cyclization [J].
Genung, Nathan E. ;
Wei, Liuqing ;
Aspnes, Gary E. .
ORGANIC LETTERS, 2014, 16 (11) :3114-3117
[28]   Solid-Phase Synthesis of Biologically Active Benzoannelated Nitrogen Heterocycles: An Update [J].
Gil, Carmen ;
Braese, Stefan .
JOURNAL OF COMBINATORIAL CHEMISTRY, 2009, 11 (02) :175-197
[29]   Preparation of Polyfunctional Indazoles and Heteroarylazo Compounds Using Highly Functionalized Zinc Reagents [J].
Haag, Benjamin ;
Peng, Zhihua ;
Knochel, Paul .
ORGANIC LETTERS, 2009, 11 (19) :4270-4273
[30]   A General and Mild Palladium-Catalyzed Domino Reaction for the Synthesis of 2H-Indazoles [J].
Halland, Nis ;
Nazare, Marc ;
R'kyek, Omar ;
Alonso, Jorge ;
Urmann, Matthias ;
Lindenschmidt, Andreas .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (37) :6879-6882