Cobalt-catalyzed tandem one-pot synthesis of polysubstituted imidazo[1,5-a]pyridines and imidazo[1,5-a]isoquinolines

被引:6
作者
Meena, Neha [1 ]
Dhiman, Shiv [1 ]
Rangan, Krishnan [2 ]
Kumar, Anil [1 ]
机构
[1] Birla Inst Technol & Sci, Dept Chem, Pilani 333031, Rajasthan, India
[2] Birla Inst Technol & Sci Pilani, Dept Chem, Hyderabad 500078, Telangana, India
关键词
H BOND FUNCTIONALIZATION; KNOEVENAGEL CONDENSATION; OXIDATIVE AMINATION; DUAL EMISSION; TRANSANNULATION; PYRIDOTRIAZOLES; DERIVATIVES; IMIDAZOLES; ACTIVATION; ARYLATION;
D O I
10.1039/d2ob00526c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient cobalt-catalyzed tandem one-pot method has been developed for the synthesis of polysubstituted imidazo[1,5-a]-N-heteroaromatics. The method involves Knoevenagel condensation followed by cobalt-catalyzed direct alkenylation to give the desired polysubstituted imidazo[1,5-a]pyridines and imidazo[1,5-a]isoquinolines in a one-pot manner. This method exhibits a broad substrate scope, provides moderate to good (39-74%) yields and is amenable to scale-up to the gram scale.
引用
收藏
页码:4215 / 4223
页数:9
相关论文
共 53 条
[1]   Imidazo[1,5-a]pyridine:: A versatile architecture for stable N-heterocyclic carbenes [J].
Alcarazo, M ;
Roseblade, SJ ;
Cowley, AR ;
Fernández, R ;
Brown, JM ;
Lassaletta, JM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (10) :3290-3291
[2]   Synthesis of imidazo[1,2-a]pyridines: a decade update [J].
Bagdi, Avik Kumar ;
Santra, Sougata ;
Monir, Kamarul ;
Hajra, Alakananda .
CHEMICAL COMMUNICATIONS, 2015, 51 (09) :1555-1575
[3]   DIRECT SYNTHESIS OF BIS(ACETYLACETONATO)NICKEL(II) DIHYDRATE AND ISOLATION OF ALPHA,ALPHA,BETA,BETA-TETRA-ACETYLETHANE AS THE OXIDATION-PRODUCT OF ACETYLACETONE [J].
BHATTACHARJEE, MN ;
CHAUDHURI, MK ;
GHOSH, SK ;
HIESE, Z ;
ROY, N .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1983, (12) :2561-2562
[4]   Pd Metal Catalysts for Cross-Couplings and Related Reactions in the 21st Century: A Critical Review [J].
Biffis, Andrea ;
Centomo, Paolo ;
Del Zotto, Alessandro ;
Zeccal, Marco .
CHEMICAL REVIEWS, 2018, 118 (04) :2249-2295
[5]  
Bluhm ME, 2002, ANGEW CHEM INT EDIT, V41, P2962, DOI 10.1002/1521-3773(20020816)41:16<2962::AID-ANIE2962>3.0.CO
[6]  
2-6
[7]   Synthesis of Imidazo[5,1-a]isoquinoline and Its 3-Substituted Analogues Including the Fluorescent 3-(1-Isoquinolinyl)imidazo[5,1-a]isoquinoline [J].
Bori, Jugal ;
Behera, Nibedita ;
Mahata, Satyajit ;
Manivannan, Vadivelu .
CHEMISTRYSELECT, 2017, 2 (35) :11727-11731
[8]   FADROZOLE HYDROCHLORIDE - A POTENT, SELECTIVE, NONSTEROIDAL INHIBITOR OF AROMATASE FOR THE TREATMENT OF ESTROGEN-DEPENDENT DISEASE [J].
BROWNE, LJ ;
GUDE, C ;
RODRIGUEZ, H ;
STEELE, RE ;
BHATNAGER, A .
JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (02) :725-736
[9]   Imidazo[1,5-a]pyridine-3-ylidenes -: pyridine derived N-heterocyclic carbene ligands [J].
Burstein, C ;
Lehmann, CW ;
Glorius, F .
TETRAHEDRON, 2005, 61 (26) :6207-6217
[10]   Transition metal-catalyzed C-H bond functionalizations by the use of diverse directing groups [J].
Chen, Zhengkai ;
Wang, Binjie ;
Zhang, Jitan ;
Yu, Wenlong ;
Liu, Zhanxiang ;
Zhang, Yuhong .
ORGANIC CHEMISTRY FRONTIERS, 2015, 2 (09) :1107-1295