Abstract
A rapid and facile one-pot three-component synthesis of biologically active 6-amino-5- cyano-4-aryl-1,4-dihydro pyrano[2,3-c] pyrazoles was developed using chitosan-p-toluene sulfonate (CS-p-TSA) as a biodegradable catalyst in an aqueous medium. The products synthesized were characterized by FT-IR, 1H-NMR, and 13C NMR. The catalyst was stable and could be used for five cycles without much change in the catalytic activity. The products synthesized were in good yields (90-96%). This method provides several advantages, including the use of a biodegradable catalyst, a simple workup procedure, mild reaction conditions, and lower reaction times.
Graphical Abstract
[http://dx.doi.org/10.1016/j.indcrop.2013.11.017]
[http://dx.doi.org/10.1073/pnas.97.13.7124]
[http://dx.doi.org/10.1021/jm00370a020] [PMID: 6708056]
[http://dx.doi.org/10.1515/znc-2006-1-201] [PMID: 16610208]
[http://dx.doi.org/10.1016/j.poly.2019.04.063]
[http://dx.doi.org/10.1002/ardp.200600057] [PMID: 16795107]
[http://dx.doi.org/10.1039/c2gc35135h]
[http://dx.doi.org/10.5012/jkcs.2018.62.2.87]
[http://dx.doi.org/10.1080/00397911.2018.1506034]
[http://dx.doi.org/10.1007/s12039-012-0310-9]
[http://dx.doi.org/10.1007/s11030-016-9708-5] [PMID: 27853977]
[http://dx.doi.org/10.1016/j.tetlet.2017.09.060]
[http://dx.doi.org/10.1007/s11164-018-3597-4]
[http://dx.doi.org/10.1002/aoc.4807]
[http://dx.doi.org/10.1016/j.molstruc.2021.131555]
[http://dx.doi.org/10.1016/j.bmcl.2012.06.055] [PMID: 22818081]
[http://dx.doi.org/10.1080/00397911.2016.1171360]
[http://dx.doi.org/10.1021/acsomega.2c01814] [PMID: 35647469]
[http://dx.doi.org/10.1016/j.ijbiomac.2019.01.027] [PMID: 30658146]
[http://dx.doi.org/10.1080/10406638.2020.1852274]
[http://dx.doi.org/10.3998/ark.5550190.0007.b18]
[http://dx.doi.org/10.1016/j.tetlet.2010.04.087]
[http://dx.doi.org/10.1039/C4GC02420F]
[http://dx.doi.org/10.1080/23312009.2015.1063830]
[http://dx.doi.org/10.1080/00397911.2015.1129668]
[http://dx.doi.org/10.1002/aoc.6656]
[http://dx.doi.org/10.1007/s13738-018-1368-1]
[http://dx.doi.org/10.1081/SCC-200043224]
[http://dx.doi.org/10.1080/00397911.2012.666315]
[http://dx.doi.org/10.4236/gsc.2013.32A001]
[http://dx.doi.org/10.1080/00397911.2020.1858109]
[http://dx.doi.org/10.2174/1570178617999200922152142]