Abstract
This review deals with the synthetic methods of pyrazolo[1,2-b]phthalazine derivatives using one-pot multi-component reactions via modern and traditional methods. The synthetic methods are subdivided into groups according to the type of reactants e.g. (1) one-pot three-component reaction of 2,3-dihydrophthalazine-1,4-dione, aldehydes and acetonitriles; (2) one-pot three-component reaction of 2,3-dihydrophthalazine-1,4-dione, aldehydes and aroyl acetonitriles; (3) one-pot three-component reaction of 2,3-dihydrophthalazine-1,4-dione, aldehydes and acetylacetone or 4-hydroxy-2H-chromen-2-one or acetylene derivatives; (4) one-pot four-component condensation reaction of phthalimide, hydrazine hydrate, aldehydes and acetonitriles; (5) one-pot four-component reaction of phthalic acid, hydrazine hydrate, indole-3- carbaldehyde and acetonitriles; and (6) one-pot three-component condensation reaction of 2,3- dihydrophthalazine-1,4-dione, aldehyde, and dimedone derivatives. Moreover, the various methods were reported.
Graphical Abstract
[http://dx.doi.org/10.1021/cr60055a001]
[http://dx.doi.org/10.1021/cr60111a001]
[http://dx.doi.org/10.1021/ar010071i] [PMID: 12234202]
[http://dx.doi.org/10.1016/j.ultsonch.2009.06.012] [PMID: 19589715]
[http://dx.doi.org/10.1016/0960-894X(96)00323-X]
[http://dx.doi.org/10.1016/j.bmcl.2003.10.027] [PMID: 14698190]
[http://dx.doi.org/10.1021/jm990383f] [PMID: 10715167]
[http://dx.doi.org/10.1016/j.jfluchem.2010.03.003]
[http://dx.doi.org/10.1111/j.1747-0285.2009.00776.x] [PMID: 19207467]
[http://dx.doi.org/10.1016/j.bmcl.2007.02.003] [PMID: 17320386]
[http://dx.doi.org/10.3390/11070574] [PMID: 17971729]
[http://dx.doi.org/10.1016/j.bmcl.2016.02.008] [PMID: 26876930]
[http://dx.doi.org/10.1039/c2gc35635j]
[http://dx.doi.org/10.1007/s11030-020-10153-8] [PMID: 33150953]
[http://dx.doi.org/10.1002/1099-0690(200207)2002:13<2046:AID-EJOC2046>3.0.CO;2-C]
[http://dx.doi.org/10.1016/j.bmcl.2004.05.021] [PMID: 15203137]
[http://dx.doi.org/10.1039/C1GC16297G]
[http://dx.doi.org/10.2174/1385272825666210202122645]
[http://dx.doi.org/10.2174/1385272824666200217095341]
[http://dx.doi.org/10.2174/1570193X15666180419142511]
[http://dx.doi.org/10.1080/10406638.2020.1830129]
[http://dx.doi.org/10.1016/j.jphotochem.2020.113041]
[http://dx.doi.org/10.1016/j.dyepig.2021.109628]
[http://dx.doi.org/10.1002/jhet.1809]
[http://dx.doi.org/10.1134/S1070363217100267]
[http://dx.doi.org/10.1007/s11164-018-3435-8]
[http://dx.doi.org/10.1007/s13738-016-0989-5]
[http://dx.doi.org/10.3184/174751916X14627996968714];
(b) Raghuvanshi, D.S.; Singh, K.N. A highly efficient green synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives and their photophysical studies. Tetrahedron Lett., 2011, 52(43), 5702-5705.
[http://dx.doi.org/10.1016/j.tetlet.2011.08.111]
[http://dx.doi.org/10.1002/jccs.201300538]
[http://dx.doi.org/10.1016/j.crci.2014.01.026]
[http://dx.doi.org/10.1515/hc-2017-0142]
[http://dx.doi.org/10.1515/znb-2016-0262]
[http://dx.doi.org/10.1007/s10562-017-2032-6]
[http://dx.doi.org/10.1007/s13738-017-1068-2]
[http://dx.doi.org/10.1134/S107036321607032X]
[http://dx.doi.org/10.1039/C5RA10730J]
[http://dx.doi.org/10.1007/s11164-020-04293-7]
[http://dx.doi.org/10.1002/slct.202002099]
[http://dx.doi.org/10.1039/C4RA17067A]
[http://dx.doi.org/10.1039/D0NJ03478A]
[http://dx.doi.org/10.1002/aoc.5872]
[http://dx.doi.org/10.1002/aoc.3288]
[http://dx.doi.org/10.1080/00304948.2019.1693241]
[http://dx.doi.org/10.1080/00304948.2020.1765655]
[http://dx.doi.org/10.1080/10406638.2020.1747094]
[http://dx.doi.org/10.1007/s40097-017-0241-6]
[http://dx.doi.org/10.1002/aoc.5386]
[http://dx.doi.org/10.1007/s11164-015-2138-7]
[http://dx.doi.org/10.3390/molecules17078674] [PMID: 22825620]
[http://dx.doi.org/10.1016/j.tet.2011.07.002]
[http://dx.doi.org/10.1016/j.tetlet.2019.01.028]
[http://dx.doi.org/10.1002/jhet.3061]
[http://dx.doi.org/10.1002/hlca.200900378]
[http://dx.doi.org/10.1016/j.molcata.2013.03.003]
[http://dx.doi.org/10.1016/j.jscs.2015.08.001]
[http://dx.doi.org/10.1080/00397911.2014.888080]
[http://dx.doi.org/10.1016/j.tet.2006.09.006];
(b) Ansari, M.D.; Sagir, H.; Yadav, V.B. Magnetically recoverable Fe3O4 nanocatalyst for the synthesis of biodynamically significant 1H-pyrazolo[1,2-b]phthalazine-5,10-diones derivatives and its DFT study. Mol. Divers., 2022.
[http://dx.doi.org/10.1007/s11030-022-10532-3]
[http://dx.doi.org/10.17628/ecb.2020.9.154-159]
[http://dx.doi.org/10.17628/ecb.2018.7.324-328]
[http://dx.doi.org/10.14233/ajchem.2020.22707]
[http://dx.doi.org/10.1080/00397911.2016.1192650]
[http://dx.doi.org/10.1007/s11164-016-2565-0]
[http://dx.doi.org/10.1007/s11164-020-04135-6]
[http://dx.doi.org/10.1080/10406638.2020.1768412]
[http://dx.doi.org/10.1007/s11164-012-0969-z]
[http://dx.doi.org/10.1016/j.molliq.2012.06.007]
[http://dx.doi.org/10.1134/S1070363218090219]
[http://dx.doi.org/10.1016/j.cclet.2013.11.046]
[http://dx.doi.org/10.1002/jhet.3659]
[http://dx.doi.org/10.1007/s10593-018-2391-y]
[http://dx.doi.org/10.1016/j.mex.2020.100823] [PMID: 32195140]
[http://dx.doi.org/10.1080/00304948.2019.1697611]
[http://dx.doi.org/10.1007/s13738-016-0871-5]
[http://dx.doi.org/10.1016/j.tetlet.2012.10.063]
[http://dx.doi.org/10.1007/s00706-014-1194-9]
[http://dx.doi.org/10.5012/jkcs.2013.57.4.472]
[http://dx.doi.org/10.1155/2013/634510]
[http://dx.doi.org/10.5155/eurjchem.4.2.132-137.746]
[http://dx.doi.org/10.1007/s11164-013-1087-2]
[http://dx.doi.org/10.1016/j.molstruc.2012.11.014]
[http://dx.doi.org/10.1016/j.molliq.2012.12.006]
[http://dx.doi.org/10.1016/j.dyepig.2015.07.036]
[http://dx.doi.org/10.1166/jnn.2018.13922] [PMID: 29768885]
[http://dx.doi.org/10.1007/s11164-019-03875-4]
[http://dx.doi.org/10.1007/s11237-017-9489-7]
[http://dx.doi.org/10.1080/10426507.2016.1149853]
[http://dx.doi.org/10.1016/j.molliq.2015.02.021]
[http://dx.doi.org/10.4028/www.scientific.net/AMR.332-334.1884]
[http://dx.doi.org/10.3987/COM-12-12626]
[http://dx.doi.org/10.1080/10406638.2019.1593863]
[http://dx.doi.org/10.1016/j.tet.2012.06.045]
[http://dx.doi.org/10.1007/s11434-012-5081-7]
[http://dx.doi.org/10.3184/174751912X13251821462738]
[http://dx.doi.org/10.1016/j.tetlet.2012.01.095]
[http://dx.doi.org/10.1002/jccs.201000198]
[http://dx.doi.org/10.2298/JSC120508088K]
[http://dx.doi.org/10.1134/S1070428019020180]
[http://dx.doi.org/10.1080/00304948.2017.1384260]
[http://dx.doi.org/10.5012/jkcs.2015.59.4.280]
[http://dx.doi.org/10.1007/s11030-011-9348-8] [PMID: 22161122]
[http://dx.doi.org/10.1080/10406638.2020.1732430]
[http://dx.doi.org/10.1021/ol017256+] [PMID: 11869124]
[http://dx.doi.org/10.1021/jo00936a001]