Direct Access to Dihydrobenzoimidazo[2,1-a]isoquinolines through Ruthenium-catalyzed Formal [4+2] Annulation

被引:22
作者
Dhole, Sandip [1 ,3 ]
Sun, Chung-Ming [1 ,2 ]
机构
[1] Natl Chiao Tung Univ, Dept Appl Chem, 1001 Ta Hseuh Rd, Hsinchu 30010, Taiwan
[2] Kaohsiung Med Univ, Dept Med & Appl Chem, 100,Shih Chuan 1st Rd, Kaohsiung 80708, Taiwan
[3] Univ Pune, Chandmal Tarachand Bora Coll, Dept Chem, Shirur 412210, Maharashtra, India
关键词
Benzoimidazo[2,1-a]isoquinolines Ruthenium; 4+2] annulation; 2-aryl benzimidazole; Styrene; H BOND ACTIVATION; REGIOSELECTIVE SYNTHESIS; BENZIMIDAZOLES; HETEROCYCLES; 2-ARYLBENZIMIDAZOLES; CYCLIZATION; INDOLES; ALKYNES;
D O I
10.1002/adsc.201801241
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A facile and straightforward synthesis of benzoimidazo[2,1-a]isoquinolines through Ru(II)-catalyzed [4+2] annulation reaction of 2-aryl benzimidazole and styrene has been explored. Tentative mechanistic studies imply the current reaction involves sequential C-C/C-N bond formation through the ortho C-H activation of 2-aryl benzimidazole followed by C-N reductive elimination. This newly developed strategy is widely applicable and tolerates various 2-arylbenzimidazole and vinyl derivatives, and allows the attractive vehicle for direct construction of diverse C6-substituated benzoimidazoisoquinoline scaffold in good yields.
引用
收藏
页码:535 / 541
页数:7
相关论文
共 51 条
[1]   Carboxylate-Assisted Ruthenium-Catalyzed Alkyne Annulations by C-H/Het-H Bond Functionalizations [J].
Ackermann, Lutz .
ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (02) :281-295
[2]   Cationic Ruthenium(II) Catalysts for Oxidative C-H/N-H Bond Functionalizations of Anilines with Removable Directing Group: Synthesis of Indoles in Water [J].
Ackermann, Lutz ;
Lygin, Alexander V. .
ORGANIC LETTERS, 2012, 14 (03) :764-767
[3]   Ruthenium-catalyzed aerobic oxidative coupling of alkynes with 2-aryl-substituted pyrroles [J].
Ackermann, Lutz ;
Wang, Lianhui ;
Lygin, Alexander V. .
CHEMICAL SCIENCE, 2012, 3 (01) :177-180
[4]   Ruthenium-Catalyzed Oxidative Annulation of 6-Anilinopurines with Alkynes via C-H Activation: Synthesis of Indole-Substituted Purines/Purine Nucleosides [J].
Allu, Srinivasarao ;
Swamy, K. C. Kumara .
ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (12) :2665-2680
[5]  
Arockiam PB, 2012, CHEM REV, V112, P5879, DOI [10.1021/cr300153j, 10.1021/cr300153J]
[6]   Natural Products Containing a Nitrogen-Nitrogen Bond [J].
Blair, Lachlan M. ;
Sperry, Jonathan .
JOURNAL OF NATURAL PRODUCTS, 2013, 76 (04) :794-812
[7]   The Larger Linear N-Heteroacenes [J].
Bunz, Uwe H. F. .
ACCOUNTS OF CHEMICAL RESEARCH, 2015, 48 (06) :1676-1686
[8]   Synthesis of dihydrobenzoimidazo[2,1-a]isoquinolines [J].
Chang, Meng-Yang ;
Wu, Ming-Hao ;
Chen, Yeh-Long .
TETRAHEDRON LETTERS, 2012, 53 (32) :4156-4160
[9]   Rhodium-Catalyzed Regioselective Synthesis of Isocoumarins through Benzothiadiazine-Fused Frameworks [J].
Dalvi, Prashant B. ;
Lin, Kuang-Ling ;
Kulkarni, Manohar V. ;
Sun, Chung-Ming .
ORGANIC LETTERS, 2016, 18 (15) :3706-3709
[10]   Reduced benzimidazo[2,1-a] isoquinolines. Synthesis and cytotoxicity studies [J].
Deady, LW ;
Rodemann, T .
AUSTRALIAN JOURNAL OF CHEMISTRY, 2001, 54 (08) :529-534