Synthesis and nitration of calix[4] (aza)crowns |
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Authors: | ZHENG Qi-Yu CHEN Chuan-Feng HUANG Zhi-TangInstitute of Chemistry Chinese Academy of Sciences Beijing China |
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Affiliation: | ZHENG,Qi-Yu CHEN,Chuan-Feng HUANG,Zhi-TangInstitute of Chemistry,Chinese Academy of Sciences,Beijing 100080,China |
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Abstract: | Calix[4] (aza) crowns containing amide groups 3a-d were synthesized by the reactions of calix[4]arene (1a) or p-tert-butylcalix[4]arene (1b) with N, N'-ethylenebis(2-chloroac-etamide) (2a) or N, N'-1,2-phenylenebis(2-chloroacetamide) (2b) by one step procedure in yields of 85-90% . Calix[4]-(aza) crowns 4a-b could be obtained by the reduction of 3a-b with LiAlH4 in yields of 51 and 67% , respectively. The nitration of 3a or 3c afforded new chromogenic calix[4]arenes 5a bearing two nitrophenol moieties and 5c bearing one nitro-phenol and one quinone moiety, respectively. The ipso-nitrations of 3b and 3d were also studied. Both gave the products containing one nitrophenol and one quinone moiety. Moreover, a very interesting calix[4]arene derivative 5d containing one cyclohexadienone moiety was also separated as the main product when 3d was ipso -nitrated. |
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Keywords: | Calix[4] (aza) crown calixarene nitration reduction |
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