Abstract
We have explored the reactions of tetrahydro-4H-selenochromenes in the presence of phosphoric pentachloride, and synthesized new condensate aroylbenzoselenophenes. During the reactions, tetrahydro-4H-selenochromenes with phosphoric pentachloride underwent oxidative aromatization and nucleophilic substitution for a chlorine atom of one of the protons in the alicyclic fragment. Also, the narrowing of the heterocyclic fragment occurred as in synthesized selenium-containing compounds earlier transformed into the corresponding condensate aroylbenzoselenophenes.
Keywords: Synthesis, heterocycles, 2, 4-diaryltetrahydro-4H-selenochromenes, aroylbenzoselenophenes, 1, 5-diketones, pummerer rearrangement.
Graphical Abstract
[http://dx.doi.org/10.1515/hc-2014-0195]
[http://dx.doi.org/10.1016/j.bioorg.2019.01.069] [PMID: 30743174]
[http://dx.doi.org/10.3390/molecules24020336] [PMID: 30669343]
[http://dx.doi.org/10.1016/j.ejmech.2014.09.046] [PMID: 25233100]
[http://dx.doi.org/10.1097/CAD.0b013e32834618bc] [PMID: 21562407]
[http://dx.doi.org/10.1021/ol102027j] [PMID: 21053969]
[http://dx.doi.org/10.1016/j.ejmech.2007.12.006] [PMID: 18242782]
[http://dx.doi.org/10.1134/S1070428016030088]
[http://dx.doi.org/10.2174/138527210793358231]
[http://dx.doi.org/10.7868/S0026898418030151] [PMID: 29989584]
[http://dx.doi.org/10.1007/978-1-4939-8796-2_15] [PMID: 30725417]
[http://dx.doi.org/10.2174/1385272819666150810222632]
[http://dx.doi.org/10.1016/j.biopha.2018.12.146] [PMID: 30616079]
[http://dx.doi.org/10.1007/s12011-019-01771-x] [PMID: 31222623]
[http://dx.doi.org/10.1007/s12011-019-01781-9] [PMID: 31236815]
[http://dx.doi.org/10.1515/HC.2000.6.3.271]
[http://dx.doi.org/10.1515/hc-2017-0187]
[http://dx.doi.org/10.1515/hc-2018-0039]
[http://dx.doi.org/10.2174/1385272820666161020162113]
[http://dx.doi.org/10.1515/hc-2019-0001]
[http://dx.doi.org/10.1515/hc-2019-0003]
[http://dx.doi.org/10.1515/hc-2019-0004]
[http://dx.doi.org/10.2174/1385272823666191209111934]
[http://dx.doi.org/10.1021/acs.joc.8b03179] [PMID: 30740976]
[http://dx.doi.org/10.1002/jccs.201500406]
[http://dx.doi.org/10.1007/BF01169954]
[http://dx.doi.org/10.1007/BF00505956]
[http://dx.doi.org/10.1007/s11172-009-0207-z]
[http://dx.doi.org/10.1515/hc-2016-0076]
[http://dx.doi.org/10.1021/cr60297a005]