Abstract
Microwave-accelerated methods have emerged as powerful tools in organic synthesis to enhance the reaction rates and provide products with high yields, improved selectivity, lower energy consumption, mild reaction conditions and negligible waste generation. Xanthenes are an important class of biologically important oxygen-containing heterocyclic molecules that possess a multitude of pharmaceutical properties. By considering the medicinal and material significance of these molecules, a large number of synthetic methodologies and catalytic systems have been reported for the synthesis of a wide range of xanthenes in the past. However, the focus of the present review is to summarize various microwave-assisted protocols for the synthesis of diversely substituted xanthene analogues.
Keywords: Dibenzo[a, j]xanthenes, 1, 8-dioxoxanthenes, microwave irradiation, synthesis, tetrahydrobenzo[a]xanthenes, xanthones.
Graphical Abstract
[http://dx.doi.org/10.1021/cr0509410] [PMID: 17451275]
[http://dx.doi.org/10.1002/anie.200400655] [PMID: 15558676]
[http://dx.doi.org/10.1021/ar700238s] [PMID: 18419142]
[http://dx.doi.org/10.1021/ar040278m] [PMID: 16104688]
[http://dx.doi.org/10.1016/j.tet.2008.06.052]
[http://dx.doi.org/10.1039/B411438H] [PMID: 15672180]
[http://dx.doi.org/10.1016/j.jphotochemrev.2005.07.001]
[http://dx.doi.org/10.1002/open.201402123] [PMID: 26246993]
[http://dx.doi.org/10.1016/S0040-4020(01)00906-1]
[http://dx.doi.org/10.1039/c0gc00024h]
[http://dx.doi.org/10.1039/b716534j] [PMID: 18648680]
[http://dx.doi.org/10.1021/ar010074v] [PMID: 12234201]
[http://dx.doi.org/10.1039/b003752o]
[http://dx.doi.org/10.3390/molecules17067543] [PMID: 22710828]
[http://dx.doi.org/10.1007/s00284-005-0040-z] [PMID: 16392007]
[http://dx.doi.org/10.1016/j.phymed.2009.01.010] [PMID: 19303274]
[http://dx.doi.org/10.1016/j.bmcl.2009.08.033] [PMID: 19717302]
[http://dx.doi.org/10.1016/j.bmcl.2012.01.126] [PMID: 22365759]
[http://dx.doi.org/10.1016/j.bmcl.2008.07.042] [PMID: 18667305]
[http://dx.doi.org/10.1016/j.bmcl.2011.09.088] [PMID: 22014830]
[http://dx.doi.org/10.1021/np8005953] [PMID: 19296616]
[http://dx.doi.org/10.1016/j.tetlet.2015.01.162]
[http://dx.doi.org/10.1016/S0040-4020(03)00240-0]
[http://dx.doi.org/10.1021/cc900143h] [PMID: 19954208]
[http://dx.doi.org/10.1007/BF01166986] [PMID: 1214868]
[http://dx.doi.org/10.3109/14756366.2012.692087] [PMID: 22803669]
[http://dx.doi.org/10.1016/j.tetlet.2014.07.003]
[http://dx.doi.org/10.1016/j.saa.2004.07.031] [PMID: 15911383]
[http://dx.doi.org/10.1021/ja00455a017]
[http://dx.doi.org/10.1002/9780470187012]
[http://dx.doi.org/10.1016/j.tet.2005.05.043]
[http://dx.doi.org/10.1016/S0960-894X(01)00595-9] [PMID: 11677123]
[http://dx.doi.org/10.1016/j.farmac.2004.07.001] [PMID: 15474058]
[http://dx.doi.org/10.1088/0022-3727/35/13/303]
[http://dx.doi.org/10.1021/j100203a044]
[http://dx.doi.org/10.1039/b103834f]
[http://dx.doi.org/10.1016/j.tetlet.2004.10.046]
[http://dx.doi.org/10.1016/S0040-4039(00)72432-4]
[http://dx.doi.org/10.1016/j.tetlet.2003.10.065]
[http://dx.doi.org/10.1081/SCC-100103323]
[http://dx.doi.org/10.1021/ja01681a023]
[http://dx.doi.org/10.1139/v04-155]
[http://dx.doi.org/10.1016/j.catcom.2005.12.018]
[http://dx.doi.org/10.1016/j.molcata.2005.11.048]
[http://dx.doi.org/10.1016/j.molcata.2009.06.020]
[http://dx.doi.org/10.1016/j.catcom.2006.02.023]
[http://dx.doi.org/10.1016/j.catcom.2008.01.031]
[http://dx.doi.org/10.1016/j.tetlet.2012.11.058]
[http://dx.doi.org/10.1016/j.catcom.2007.01.007]
[http://dx.doi.org/10.1016/j.molcata.2007.05.007]
[http://dx.doi.org/10.1016/j.molcata.2006.04.007]
[http://dx.doi.org/10.1016/j.apcata.2007.03.008]
[http://dx.doi.org/10.1080/00397911.2010.486507]
[http://dx.doi.org/10.1016/j.tetlet.2008.03.124]
[http://dx.doi.org/10.1016/j.bmcl.2007.07.008] [PMID: 18055199]
[http://dx.doi.org/10.1016/j.dyepig.2007.02.001]
[http://dx.doi.org/10.1016/j.tet.2009.06.024]
[http://dx.doi.org/10.3762/bjoc.7.9] [PMID: 21286395]
[http://dx.doi.org/10.1080/00397910802638511]
[http://dx.doi.org/10.1016/j.tetlet.2009.06.029]
[http://dx.doi.org/10.1016/j.tetlet.2010.02.149]
[http://dx.doi.org/10.1007/s00706-009-0204-9]
[http://dx.doi.org/10.1002/(SICI)1099-0690(199809)1998:9<2031:AID-EJOC2031>3.0.CO;2-#]
[http://dx.doi.org/10.1021/ol203381q] [PMID: 22272652]
[http://dx.doi.org/10.1039/b900931k]
[http://dx.doi.org/10.1021/ol0517731] [PMID: 16146405]
[http://dx.doi.org/10.1080/00397911.2012.736584]
[http://dx.doi.org/10.1007/s11144-012-0499-0]
[http://dx.doi.org/10.1016/j.jscs.2013.12.003]
[http://dx.doi.org/10.1016/j.cdc.2019.100201]
[http://dx.doi.org/10.1016/j.tetlet.2005.10.057]
[http://dx.doi.org/10.1016/j.mencom.2007.06.023]
[http://dx.doi.org/10.1002/cjoc.200790120]
[http://dx.doi.org/10.1016/j.catcom.2006.11.003]
[http://dx.doi.org/10.1002/cjoc.200890065]
[http://dx.doi.org/10.1016/j.crci.2012.05.018]
[http://dx.doi.org/10.5267/j.ccl.2012.12.002]
[http://dx.doi.org/10.2298/JSC130805021K]
[http://dx.doi.org/10.1039/C5RA19645K]
[http://dx.doi.org/10.25135/acg.oc.53.18.11.1051]
[http://dx.doi.org/10.1038/srep42975] [PMID: 28233832]
[http://dx.doi.org/10.1002/jhet.3162]
[http://dx.doi.org/10.31788/RJC.2019.1215043]
[http://dx.doi.org/10.1080/17518253.2010.544260]
[http://dx.doi.org/10.1002/jhet.742]
[http://dx.doi.org/10.1080/00397911.2010.544832]
[http://dx.doi.org/10.1039/c2cy20041d]
[http://dx.doi.org/10.1007/s11164-014-1821-4]
[http://dx.doi.org/10.1007/s00706-011-0577-4]
[http://dx.doi.org/10.2174/221333560201150212102647]
[http://dx.doi.org/10.1021/ol101100d] [PMID: 20533853]
[http://dx.doi.org/10.1021/ol101496w] [PMID: 20704333]
[http://dx.doi.org/10.1021/jo1013614] [PMID: 20738144]
[http://dx.doi.org/10.1039/C8OB01684D] [PMID: 30124720]