【摘 要】
:
1,5-Benzodiazepine is a kind of extremely significant compounds,which have high biologicaland pharmacological activity in the last decades.1 Previous studies on 1,5-benzodiazepines have indicated that
【机 构】
:
The College of Chemistry and Material Science Hebei Normal University Shijiazhuang 050024
【出 处】
:
中国化学会第十六届全国有机合成化学学术研讨会
论文部分内容阅读
1,5-Benzodiazepine is a kind of extremely significant compounds,which have high biologicaland pharmacological activity in the last decades.1 Previous studies on 1,5-benzodiazepines have indicated that free ester and acyl groups at different positions in the nuclei of the molecules can enhance the pharmacological properties of the compounds.2 Consequently,in view of our continuous interest in the synthesis of 1,5-benzodiazepine derivatives,we wished to synthesize 1,5-benzodiazepines with C2-position ester group and C3-position acyl group on the seven-membered ring structure.A multicomponent or domino reaction is one of the most desirable methods due to its efficient atom economy and green characteristics.3 Thus we have designed and one-pot synthesized a series of novel substituted 2-esteryl-3-acyl-1,5-benzodiazepines compounds via domino reactions(Scheme1).The compound(1)was obtained by two nucleophilic substitution reactions of acetophenone and N,N-dimethylformamide dimethyl acetal with the removal of the methanol molecules.And then,the compounds(2)were synthesized via nucleophilic substitution reaction.Finally,the compounds(3)were obtained via nucleophilic addition,dehydration,cyclization and hydrogen transfer of compound(2)with ethyl pyruvate.Six target compounds(3)were finally obtained via above domino reactions with excellent yields(80%-92%).These compounds are determined by 1H NMR,13C NMR,MS,and IR.Simple operation,short reaction time,high yields are the advantages of this synthesis method.
其他文献
氮氧螺杂环骨架广泛存在于天然产物的核心结构中,具有独特的生物活性,如钙通道抑制活性(LycoplanineA),以及对多种肿瘤的抗增殖活性(青霉素A).Diels-Alder(DA)反应是构建六元环体系最重要和最基础的方式之一.目前为止,只有少数报道了对映体选择性反电子需求氧杂Diels-Alder反应,它们主要利用,α,β-不饱和羰基化合物作为双烯化合物与富电子烯烃进行环加成反应.1因此,研究其
A series of new potentially multi-targeting antimicrobial naphthalimide-derived fluconazole analogs were designed and conveniently synthesized from 4-bromonaphthalic anhydride.Their structures were ch
As an important class of N-heterocycles,quinazoline derivatives are prevalent in many nature products and synthetic drugs with wide therapeutic and pharmacological applications.1 Due to the importance
As a privileged N-heterocycle,imidazo[1,2-α]pyridines have exhibited various biological activities.1 With properly installation of amidomethyl,hydroxylmethyl,or other groups at C3 position followed by
Transition-metal-catalyzed C-H functionalization has been extensively investigated with great application in the syntheses of bioactive molecule and functional materials.1Meanwhile,catalytic C-C bond-
Copper plays an important role in many physiological activities,and its concentration above or below the normal levels will cause an adverse effect on the organism.1 Therefore,the design and synthesis
Alkylation reaction utilizing alcohols as alkylating reagents through a borrow-hydrogen(BH)or hydrogen autotransfer(HA)strategy has emerged as a powerful tool to construct C-C bonds.1,2 During these t
众所周知,偶氮官能团是一类重要的结构单元,广泛分布于染料分子、颜料分子、药物分子、食品添加剂、有机试剂和材料分子中.例如,甲基红和甲基橙均是芳香类偶氮衍生物,可用作染料和指示剂;百浪多息是一种芳香族偶氮化合物.它不仅是一种简单的染料,更为重要的是它是第一个合成的磺胺抗菌药物;偶氮二甲酸二乙酯(DEAD)、偶氮二甲酸二异丙酯(DIAD)均是Mitsunobu反应中的必需试剂.由于偶氮化合物的重要性和
Spirocyclohexadienones and pyrazolines are prevalent core structures in bioactive molecules1 and natural products.2 On the other hand,spiro compounds have continued to gain attentions in recent years
叔膦等路易斯碱催化联烯酸酯的反应发展多年来,多种反应类型及其手性合成被发现报道,如Umpolung加成、[m+n]环加成、Rauhut-Currier反应等,在一些药物分子合成及全合成中该方法学也被广泛应用.1值得注意的是,1992年Trost课题组首次发现联烯酸酯可以在叔膦催化作用下异构成共轭二烯的反应(图1),2该方法迅速被研究并成为构建分子内共轭二烯类的一种重要方法.3在过去的几十年里,还没