Multicomponent Cross-Dehydrogenative Coupling of Imidazo[1,2-a]pyridine: Access to Abnormal Mannich and Mannich-Type Reaction

被引:3
作者
Rahaman, Segufa [1 ]
Sahay, Suhag Singh [1 ]
Kumari, Annu [1 ]
Dey, Swapan [1 ]
机构
[1] Indian Inst Technol, Indian Sch Mines, Dept Chem & Chem Biol, Dhanbad 826004, Jharkhand, India
关键词
C-H ACTIVATION; BIOLOGICAL EVALUATION; DERIVATIVES; CHEMISTRY; BONDS; IMIDAZOPYRIDINE; RECEPTORS; DESIGN;
D O I
10.1021/acs.joc.4c01001
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
This study showcases successfully switchable approaches to accomplish the C3-aryl methylation and C3-amino methylation of privileged nitrogen-containing pharmaceutical compounds "imidazopyridines" with distinct amines, which surmounts the long-standing requirement for a superfluous directing group. These two transformations manifest pronounced regio- and chemo-divergent behavior, successfully demonstrating unprecedented multicomponent "abnormal Mannich and Mannich-type" reactions. The remarkable environmentally benign protocol has been efficiently extended to concise the synthesis and late-stage derivatization.
引用
收藏
页码:10773 / 10784
页数:12
相关论文
共 62 条
[1]   Synthesis and Antibacterial Activity of New Imidazo[1,2-a]pyridines Festooned with Pyridine, Thiazole or Pyrazole Moiety [J].
Althagafi, Ismail ;
Abdel-Latif, Ehab .
POLYCYCLIC AROMATIC COMPOUNDS, 2022, 42 (07) :4487-4500
[2]   Green Chemistry: Principles and Practice [J].
Anastas, Paul ;
Eghbali, Nicolas .
CHEMICAL SOCIETY REVIEWS, 2010, 39 (01) :301-312
[3]   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
[4]   The 100 facets of the Passerini reaction [J].
Banfi, Luca ;
Basso, Andrea ;
Lambruschini, Chiara ;
Moni, Lisa ;
Riva, Renata .
CHEMICAL SCIENCE, 2021, 12 (47) :15445-15472
[5]  
Bergman RG, 2007, NATURE, V446, P391, DOI 10.1038/446391a
[6]   Imidazo[1,2-a]pyridin-3-amines as potential HIV-1 non-nucleoside reverse transcriptase inhibitors [J].
Bode, Moira L. ;
Gravestock, David ;
Moleele, Simon S. ;
van der Westhuyzen, Christiaan W. ;
Pelly, Stephen C. ;
Steenkamp, Paul A. ;
Hoppe, Heinrich C. ;
Khan, Tasmiyah ;
Nkabinde, Lindiwe A. .
BIOORGANIC & MEDICINAL CHEMISTRY, 2011, 19 (14) :4227-4237
[7]  
Boerner RJ, 1997, PSYCHOPHARMAKOTHERAP, V4, P145
[8]   Kilogram-Scale Synthesis of the CXCR4 Antagonist GSK812397 [J].
Boggs, Sharon ;
Elitzin, Vassil I. ;
Gudmundsson, Kristjan ;
Martin, Michael T. ;
Sharp, Matthew J. .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2009, 13 (04) :781-785
[9]   Green chemistry approaches to the synthesis of 5-alkoxycarbonyl-4-aryl-3,4-dihydropyrimidin-2(1H)-ones by a three-component coupling of one-pot condensation reaction:: Comparison of ethanol, water, and solvent-free conditions [J].
Bose, DS ;
Fatima, L ;
Mereyala, HB .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (02) :587-590
[10]   Boronic Acids and Esters in the Petasis-Borono Mannich Multicomponent Reaction [J].
Candeias, Nuno R. ;
Montalbano, Francesco ;
Cal, Pedro M. S. D. ;
Gois, Pedro M. P. .
CHEMICAL REVIEWS, 2010, 110 (10) :6169-6193