CAS: 79603-03-5; 4-Bromo-2-Nitrobenzonitrile

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N-(3-Bromophenyl)-2-Hydroxyiminacetamide置于2,6-二甲基吡啶,三氟甲磺酸酐,硫酸,盐酸羟胺,三氟乙酸体系中,用 乙醇,二氯甲烷,水 作为反应溶剂,化学反应 19.17H,反应生成 2-硝基-4-溴苯腈
参考文献:Synthesis And Dual D₂ And 5-Ht_1A Receptor Binding Affinities Of 7-Piperazinyl And 7-Piperidinyl-3,4-Dihydroquinazolin-2(1H)-Ones
标题:Synthesis And Dual D₂ And 5-Ht_1A Receptor Binding Affinities Of 7-Piperazinyl And 7-Piperidinyl-3,4-Dihydroquinazolin-2(1H)-Ones
摘要:一系列新的7-哌嗪基和7-哌啶基-3,4-二氢喹唑啉-2(1H)-酮已被合成.所述化合物在结构上与阿多拉嗪相关,后者是一种潜在的不典型抗精神病药物,具有强效的d2受体拮抗剂和5-Ht1A受体激动剂特性.制备了适当修饰的芳基溴化物,并与叔丁基哌嗪-1-羧酸酯缩合,得到高级中间体哌嗪基-3,4-二氢喹唑啉-2(1H)-酮.同样,Suzuki-Miyaura交叉偶联反应中,环状乙烯基硼酸盐与适当的芳基溴化物反应,得到哌啶基-3,4-二氢喹唑啉-2(1H)-酮.通过哌嗪基和哌啶基-3,4-二氢喹唑啉-2(1H)-酮与适当设计的联芳基醛的还原胺化反应,完成了这些目标化合物的合成.所述化合物被筛选为d2和5-Ht1A受体结合亲和力.结构-活性关系研究表明,环戊烯基吡啶和环戊烯基苄基对这些化合物的双重d2和5-Ht1A受体结合亲和力有显著贡献.
DOI:10.2174/15734064113096660046

专利信息

专利号:US-9073900-B2
优先权日:2013-10-02
标题:Dihydroquinone derivatives of piperidine and piperazine
发明人：ULLAH NISAR
权利人:UNIV KING FAHD PET & MINERALS; KING ABDULAZIZ CITY SCI & TECH
摘要:The dihydroquinone derivatives of piperidine and piperazine are 7-piperazinyl and 7-piperadinyl-3,4-dihydroquinazolin-2(1H)-ones that exhibit D 2 and 5-HT 1A receptor binding affinities, making them suitable for use as the active ingredient of pharmaceuticals for the treatment of schizophrenia. The derivatives have the general formula: n nwhere X is carbon or nitrogen and R is a group selected from a through f having the formula:n n nor a pharmaceutically acceptable salt thereof. The piperazine compounds are prepared by condensing 4-bromo-2-nitro-benzonitrile with 1-Boc-piperazine (1-tert-butoxycarbonyl-piperazine) to form an intermediate that is converted to a piperazinyl-3,4-dihydroquinazolin-2(1H)-one. Subsequent reductive amination with the biarylaldehydes a through f completes the synthesis of the 7-piperadinyl-3,4-dihydroquinazolin-2(1H)-ones. The piperadinyl compounds are prepared from tert-butyl-4-(2-oxo-1,2,3,4-tetradihydroquinazolin-7-yl)piperidine-1-carboxylate, which is converted to 7-(piperidin-4-yl)-3,4-dihyroquinazolin-2(1H)-one. Subsequent reductive amination with the biarylaldehydes a through f completes the synthesis of the 7-piperidinyl-3,4-dihydroquinazolin-2(1H)-ones.