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Synthesis and nitration of calix[4] (aza)crowns
  • ISSN号:1001-604X
  • 期刊名称:《中国化学:英文版》
  • 时间:0
  • 分类:O624[理学—有机化学;理学—化学]
  • 作者机构:Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080, China, China
  • 相关基金:Project (Nos. 29602010, 29772037) supported by the National Natural Science Foundation of China.
中文摘要:

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.

英文摘要:

Calix[4] (aza) crowns containing amide groups 3a—d were synthesized by the reactions of calix[4]arene (la) or p-tert-butylcalix[4]arene (1b) with N, N′-ethylenebis(2-chloroacetamide) (2a) or N, N′- 1,2-ethylenebis (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-nitration's of 3b and 3d were also studied. Both gave the products containing one nitro phenol and one quinine 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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期刊信息
  • 《中国化学:英文版》
  • 主管单位:
  • 主办单位:中国化学会
  • 主编:
  • 地址:上海市枫林路354号中科院上海有机化学研究所
  • 邮编:200032
  • 邮箱:
  • 电话:021-54925243
  • 国际标准刊号:ISSN:1001-604X
  • 国内统一刊号:ISSN:31-1547/O6
  • 邮发代号:4-646
  • 获奖情况:
  • 中国期刊方阵“双高”期刊
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  • 美国化学文摘(网络版),荷兰文摘与引文数据库,美国科学引文索引(扩展库),日本日本科学技术振兴机构数据库,英国英国皇家化学学会文摘
  • 被引量:175