蒙脱土负载路易斯酸催化1,5-苯二氮杂卓衍生物的合成
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摘要
以蒙脱土负载路易斯酸为催化剂,催化邻苯二胺和酮经缩合反应合成5个1,5-苯二氮杂卓衍生物,其结构经~1H NMR和IR确证。并对反应条件进行优化了优化。最优反应条件为:n(邻苯二胺)∶n(苯乙酮)=1.0∶2.5, MMT/NiCl_2 10 mol%为催化剂,正己烷为溶剂,于70℃反应10 h,收率最高为93.0%。
Five 1,5-benzodiazepine derivatives were synthesized catalyzed by montmorillonite loaded Lewis acid, using o-phenylenediamine and ketone as raw materials. The structures were confirmed by ~1H NMR and IR. The reaction conditions were optimized. The results showed that the optimal conditions were as follows: n(o-phenylenediamine) ∶n(acetophenone)=1.0 ∶2.5, 10 mol% MMT/NiCl_2 as the catalyst, n-hexane as solvent, reaction at 70 ℃ for 10 h, the yield was up to 93.0%.
Five 1,5-benzodiazepine derivatives were synthesized catalyzed by montmorillonite loaded Lewis acid, using o-phenylenediamine and ketone as raw materials. The structures were confirmed by ~1H NMR and IR. The reaction conditions were optimized. The results showed that the optimal conditions were as follows: n(o-phenylenediamine) ∶n(acetophenone)=1.0 ∶2.5, 10 mol% MMT/NiCl_2 as the catalyst, n-hexane as solvent, reaction at 70 ℃ for 10 h, the yield was up to 93.0%.
引文
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[3] 王莎莎,王兰芝.新型1,5-苯并二氮杂卓衍生物的结构与抑菌活性的理论分析[J].化学研究与应用,2014,26(3):376-383.
[4] KONDA S G,SHAIKH B M,CHAVAN S A,et al.Polyethyleneglycol(PEG-400):An efficient and recyclable reaction medium for the synthesis of novel 1,5-benzodiazepines and their antimicrobial activity[J].Chinese Chemical letters,2011,22(1):65-68.
[5] LOPEZMUNOZ F,ALAMO C,GARCIAGARCIA P.The discovery of chlordiazepoxide and the clinical introduction of benzodiazepines:Half a century of anxiolytic drugs[J].Journal of Anxiety Disorders,2011,25(4):554-62.
[6] CHEN Y B,LE V,XU X Y,et al.Discovery of novel 1,5-benzodiazepine-2,4-dione derivatives as potential anticancer agents[J].Bioorganic & Medicinal Chemistry Letters,2014,24(16):3948-3951.
[7] 王兰芝,花中霞,王莎莎.2-乙氧羰基(羧基)-4-取代苯基-2,3-二氢-1H-苯并[b][1,4]二氮杂卓的合成及抑菌活性测定[J].有机化学,2013,33(11):2376-2383.
[8] WANG L Z,LI X Q,AN Y S.1,5-Benzodiazepine derivatives as potential antimicrobial agents:Design,synthesis,biological evaluation,and structure-activity relationships[J].Organic & Biomolecular Chemistry,2015,13(19):5497-5509.
[9] MARIAPPAN B,KASI P,PENUGONDA R.Synthesis of 5-benzyl-4-aryl-octahydro-1H-benzo[b][1,5]diazepin-2-ones as potent antidepressant and antimicrobial agents[J].Medicinal Chemistry Research,2014,23(4):2070-2079.
[10] GOSWAMI S V,THORAT P B,BHUSARE S R.Phenylboronic acid catalysed synthesis of 1,5-benzodiazepines via cyclocondensation of o-phenylenediamine and ketones[J].Journal of Chemical Sciences,2013,125(4):745-749.
[11] ELEFTHERIADIS N,NEOCHORITIS C G,TSOLERIDIS C A,et al.One-pot microwave assisted synthesis of new 2-alkoxycarbonylmethylene-4-oxo-1,5-benzo-,naphtho-,and pyridodiazepines and assessment of their cytogenetic activity[J].European Journal of Medicinal Chemistry,2013,45(5):302-309.
[12] LAL M,BASHA R S,SARKAR S,et al.2,6-Pyridinedicarboxylic acid as organocatalyst for the synthesis of 1,5-benzodiazepines through one-pot reaction[J].Tetrahedron Letters,2013,54(32):4264-4272.
[13] 王兰芝,花中霞,牛文刚.1,5-苯并二氮杂卓衍生物的合成及其生物活性的研究进展[J].有机化学,2010,30(11):1664-1671.
[14] PASQUALE G A,RUIZ D M,JIOS J L,et al.Preyssler catalyst-promoted rapid,clean,and efficient condensation reactions for 3H-1,5-benzodiazepine synthesis in solvent-free conditions[J].Tetrahedron Letters,2013,54(48):6574-6579.
[15] JADHAV A H,CHINNAPPAN A,PATIL R H,et al.Short oligo ethylene glycolic tailor-made ionic liquids as highly efficient and reusable catalyst for one-pot synthesis of 1,5-benzodiazepine derivatives under solvent free condition[J].Chemical Engineering Journal,2014,240(6):228-234.
[16] ZHOU X,ZHANG M Y,GAO S T,et al.An efficient synthesis of 1,5-benzodiazepine derivatives catalyzed by boric acid[J].Chinese Chemical Letters,2009,20(8):905-908.
[17] 王琳琳,尹晓刚,吴小云,等.一锅法合成喹喔啉衍生物[J].贵州师范大学学报(自然版),2017,35(3):98-102.
[18] 尹晓刚,吴小云,王野,等.微波辅助法合成3,4-二氢嘧啶-2(1H)-酮衍生物[J].贵州师范大学学报(自然版),2016,34(3):79-84.
[19] 吴伟,吴小云,吴江,等.负载型蒙脱土催化芦竹碱的微波合成[J].合成化学,2015,23(6):543-546.