Synthesis of α-Ketone-isoquinoline Derivatives via Tandem Ruthenium(II)-Catalyzed C-H Activation and Annulation

被引:34
作者
Wu, Xiao-Lin [1 ]
Dong, Lin [1 ]
机构
[1] Sichuan Univ, West China Sch Pharm, Educ Minist, Key Lab Drug Targeting & Drug Delivery Syst, Chengdu 610041, Sichuan, Peoples R China
关键词
PALLADIUM-CATALYZED IMINOANNULATION; AROMATIC KETIMINES; CARDIOTONIC AGENTS; ALKYNES; PYRIDINES; 4-AROYL-1,3-DIHYDRO-2H-IMIDAZOL-2-ONES; BENZYLAMINES; CYCLIZATION; QUINOLINES; ACYLATION;
D O I
10.1021/acs.orglett.8b02759
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new ruthenium(II)-catalyzed tandem C-H activation/cyclization/hydrolysis cascade process of 2H-imidazoles and alkynes for facile and regioselective access to alpha-ketone-isoquinolines has been successfully developed. 2H-Imidazole as the novel traceless directing group has been well applied in this paper. The protocol features mild reaction conditions and easily accessible starting materials, and alpha-ketone-isoquinolines could be applied to further construct more complex heterocyclic compounds.
引用
收藏
页码:6990 / 6993
页数:4
相关论文
共 51 条
[1]   β-phenylethylamines and the isoquinoline alkaloids [J].
Bentley, KW .
NATURAL PRODUCT REPORTS, 2004, 21 (03) :395-424
[2]   Metal-free decarboxylative acylation of isoquinolines using α-keto acids in water [J].
Chaubey, Narendra R. ;
Singh, Krishna Nand .
TETRAHEDRON LETTERS, 2017, 58 (24) :2347-2350
[3]   Discovery of a series of nonpeptide small molecules that inhibit the binding of insulin-like growth factor (IGF) to IGF-binding proteins [J].
Chen, C ;
Zhu, YF ;
Liu, XJ ;
Lu, ZX ;
Xie, Q ;
Ling, N .
JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (23) :4001-4010
[4]   ELECTROLYTIC OXIDATION OF KETONES IN AMMONIACAL METHANOL IN THE PRESENCE OF CATALYTIC AMOUNTS OF KI [J].
CHIBA, T ;
SAKAGAMI, H ;
MURATA, M ;
OKIMOTO, M .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (21) :6764-6770
[5]   A regioselective synthesis of 1-haloisoquinolines via ruthenium-catalyzed cyclization of O-methylbenzohydroximoyl halides with alkynes [J].
Chinnagolla, Ravi Kiran ;
Pimparkar, Sandeep ;
Jeganmohan, Masilamani .
CHEMICAL COMMUNICATIONS, 2013, 49 (35) :3703-3705
[6]   Ruthenium-Catalyzed Highly Regioselective Cyclization of Ketoximes with Alkynes by C-H Bond Activation: A Practical Route to Synthesize Substituted Isoquinolines [J].
Chinnagolla, Ravi Kiran ;
Pimparkar, Sandeep ;
Jeganmohan, Masilamani .
ORGANIC LETTERS, 2012, 14 (12) :3032-3035
[7]   Diphenyl quinolines and isoquinolines: Synthesis and primary biological evaluation [J].
Croisy-Delcey, M ;
Croisy, A ;
Carrez, D ;
Huel, C ;
Chiaroni, A ;
Ducrot, P ;
Bisagni, E ;
Jin, L ;
Leclercq, G .
BIOORGANIC & MEDICINAL CHEMISTRY, 2000, 8 (11) :2629-2641
[8]   Rhodium-catalyzed oxidative coupling of aromatic imines with internal alkynes via regioselective C-H bond cleavage [J].
Fukutani, Tatsuya ;
Umeda, Nobuyoshi ;
Hirano, Koji ;
Satoh, Tetsuya ;
Miura, Masahiro .
CHEMICAL COMMUNICATIONS, 2009, (34) :5141-5143
[9]   Palladium-Catalyzed Annulation of Acyloximes with Arynes (or Alkynes) Synthesis of Phenanthridines and Isoquinolines [J].
Gerfaud, Thibaud ;
Neuville, Luc ;
Zhu, Jieping .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (03) :572-577
[10]  
Gu Y, 2013, J COMB OPTIM, P1