Abstract
This review described the preparation of 2-chloroquinoline-3-carbaldehyde derivatives through Vilsmeier-Haack formylation of N-arylacetamides and their use as a key intermediate for the preparation of 2-aminoquinoline-3-carbaldehydes. The synthesis of the 2-aminoquinolines can be done through the following chemical reactions: Claisen-Schmidt condensation, 1, 3-dipolar cycloaddition, one-pot multicomponent reactions (MCRs), and reductive amination.
Keywords: 2- chloroquinoline-3-carbaldehyde, 2-aminoquinoline-3-carbaldehydes, Vilsmeier-Haack, synthesis, reactivity.
Graphical Abstract
[http://dx.doi.org/10.1039/C4RA01814A]
[http://dx.doi.org/10.1007/s10870-015-0595-x]
[http://dx.doi.org/10.1016/j.tetlet.2015.07.031]
[http://dx.doi.org/10.1016/j.bmc.2014.09.040] [PMID: 25311562]
[http://dx.doi.org/10.1016/j.bmcl.2013.12.067] [PMID: 24468411]
[http://dx.doi.org/10.1016/j.molstruc.2014.08.033]
[http://dx.doi.org/10.1016/j.bmc.2012.12.011] [PMID: 23294829]
[http://dx.doi.org/10.1016/j.ejmech.2012.08.039] [PMID: 23043766]
[http://dx.doi.org/10.1016/S0960-894X(00)00378-4]
[http://dx.doi.org/10.1128/AAC.37.4.859] [PMID: 8494383]
[http://dx.doi.org/10.2174/157340611797928334] [PMID: 22313306]
[http://dx.doi.org/10.1007/s11164-016-2794-2]
[http://dx.doi.org/10.2174/1570193X1966622032816345]
[http://dx.doi.org/10.2174/1570193X18666210218212719]
[http://dx.doi.org/10.1080/10426500701792933]
[http://dx.doi.org/10.1016/S0040-4039(01)94745-8]
[http://dx.doi.org/10.1039/p19810001520]
[http://dx.doi.org/10.1016/j.tetlet.2006.08.086]
[http://dx.doi.org/10.1080/00397911.2020.1769673]
[http://dx.doi.org/10.1007/s11030-012-9358-1]
[http://dx.doi.org/10.1016/j.tet.2009.06.036]
[http://dx.doi.org/10.1016/j.tetlet.2011.12.125]
[http://dx.doi.org/10.1080/00397911.2010.505701]
[http://dx.doi.org/10.1007/s10593-011-0725-0]
[http://dx.doi.org/10.1080/00397910802401142]
[http://dx.doi.org/10.1002/jhet.2245]
[http://dx.doi.org/10.1002/jhet.2126]
[http://dx.doi.org/10.3390/molecules]
[http://dx.doi.org/10.3987/COM-07-11260]
[http://dx.doi.org/10.1134/S1070363214060309]
[http://dx.doi.org/10.1134/S1070363219020233]
[http://dx.doi.org/10.1039/C8DT02947D] [PMID: 30507985]