Water Extract of Onion Catalyst: A Sustainable Approach for the Synthesis of 4-Substituted 1,5-Benzodiazepine Derivatives via an In Situ Generated Enaminones

IF 0.9 Q4 CHEMISTRY, PHYSICAL Current Organocatalysis Pub Date : 2023-11-10 DOI:10.2174/0122133372276924231106052151
Loganathan Selvaraj, Rajendran Eswaran, Vennila Kailasam Natesan, Seenivasa Perumal Muthu
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Abstract

Aim: To develop a green protocol for the one-pot synthesis of biologically active 4- substituted-1,5-benzodiazepine derivatives. Background: Benzodiazepines acquired significant attention in medicinal chemistry owing to their wide spectrum of biological and pharmacological activities such as anti-HIV (reverse transcriptase inhibitor) drugs, HIV-1 protease inhibiting, hepatitis C virus (HCNV) NS5B, anti-malarial, antibacterial, anti-inflammatory, anti-depressant, anti-coagulant, analgesic agents, anti-cancer, cholecystokinin- B receptor antagonists. It was made through three-component condensation of 1,2-diamine, 1,3-cyclic diketone and an aldehyde under various conditions such as (COOH)2/H2O, AcOH/EtOH. Method: 1. To develop simple, convenient and environmentally benign green protocol for the onepot synthesis of 4-substituted-1,5-benzodiazepines through three-component reaction of 1,2-diamine, 1,3-cyclic diketone with an aldehyde catalyzed by water extract of onion. 2. To optimize the reaction conditions. 3. To study scope and mechanism of the reaction 4. To characterize the structure by single crystal X-ray analysis. Result: Finally, EtOH and 0.5 mL of onion extract are suitable for reaction conditions. 4. To examine the electronic effect on reaction time and yields, the aromatic aldehydes having electron releasing functional group such as 4-OH, 4-N,N-dimethyl, 4-OMe, 4-Me, phenyl, and 3,4-dimethoxy gave the desired product in good yields. (90-92%; 5a-5e and 5m). The aromatic aldehydes bearing electron withdrawing group such as 4-Br, 4-Cl, 4-F, 4-CF3, 4-CN, 4-NO2, 3,4-dichloro, 3-bromo- 4-fluoro gave excellent yields (93-97%; 5f-5k, 5n and 5o). 5. Further, to expand the diamine substrates, we have employed 4-hydroxybenzaldehyde 4a, benzaldehyde 4e and 4-nitrobenzaldehyde 4k as model substrates and examined different diamines (4-methylbenzene-1,2-diamine 1b and 4- chlorobenzene-1,2-diamine 1c) with dimedone 2a and gave good yields (89-92%; 5v-5z and 5aa. 6. substituted-1,5-benzodiazepines. Further, the methodology was applied to large-scale reactions. Conclusion: In conclusion, employing aqueous onion extract as a gentle, affordable catalyst, we have developed a simple, effective, and environmentally friendly method for the synthesis of 4- substituted-1,5-benzodiazepines derivatives from 1,2-diamine, diketone, and an aldehyde. Excellent yields, simple workup, inexpensive, non-toxic, and environment-friendly reaction conditions are the prominent features of this procedure.
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洋葱催化剂的水提物:通过原位生成胺酮合成4-取代1,5-苯二氮卓类衍生物的可持续方法
目的:建立具有生物活性的4-取代-1,5-苯二氮卓类衍生物的绿色一锅合成工艺。背景:苯二氮卓类药物由于具有广泛的生物学和药理活性,如抗hiv(逆转录酶抑制剂)药物、HIV-1蛋白酶抑制剂、丙型肝炎病毒(HCNV) NS5B、抗疟疾、抗菌、抗炎、抗抑郁、抗凝血、镇痛、抗癌、胆囊收缩素- B受体拮抗剂等,在药物化学领域受到了广泛的关注。它是由1,2-二胺、1,3-环二酮和一种醛在(COOH)2/H2O、AcOH/EtOH等不同条件下三组分缩合而成。方法:1。以洋葱水提物为催化剂,1,2-二胺,1,3-环二酮与醛三组分反应,建立一锅法合成4-取代-1,5-苯二氮卓类化合物的简单、方便、环保的绿色方案。2. 优化反应条件。3.研究反应范围和反应机理。用单晶x射线分析表征其结构。结果:最终以乙酸乙酯和0.5 mL洋葱提取物为适宜的反应条件。4. 为了考察电子对反应时间和产率的影响,采用具有电子释放官能团的芳香醛,如4-OH、4-N、n -二甲基、4-OMe、4-Me、苯基和3,4-二甲氧基,得到了产率较高的期望产物。(90 - 92%;5a-5e和5m)。含吸电子基团的芳香醛,如4-溴、4-氯、4-氟、4-CF3、4-CN、4-NO2、3,4-二氯、3-溴- 4-氟,产率优异(93-97%;5f-5k, 5n和5o)。5. 此外,为了扩大二胺底物,我们以4-羟基苯甲醛4a、苯甲醛4e和4-硝基苯甲醛4k为模型底物,用二美酮2a检测了不同的二胺(4-甲基苯-1,2-二胺1b和4-氯苯-1,2-二胺1c),得到了良好的产率(89-92%;5v-5z和5aa。6. substituted-1 5-benzodiazepines。此外,该方法还应用于大规模反应。结论:本研究以水相洋葱提取物为催化剂,建立了一种简单、高效、环保的1,2-二胺、二酮和醛为原料合成4-取代-1,5-苯二氮卓类化合物的方法。收率高、处理简单、价格低廉、无毒、环境友好是该工艺的突出特点。
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来源期刊
Current Organocatalysis
Current Organocatalysis CHEMISTRY, PHYSICAL-
CiteScore
2.00
自引率
0.00%
发文量
28
期刊介绍: Current Organocatalysis is an international peer-reviewed journal that publishes significant research in all areas of organocatalysis. The journal covers organo homogeneous/heterogeneous catalysis, innovative mechanistic studies and kinetics of organocatalytic processes focusing on practical, theoretical and computational aspects. It also includes potential applications of organocatalysts in the fields of drug discovery, synthesis of novel molecules, synthetic method development, green chemistry and chemoenzymatic reactions. This journal also accepts papers on methods, reagents, and mechanism of a synthetic process and technology pertaining to chemistry. Moreover, this journal features full-length/mini review articles within organocatalysis and synthetic chemistry. It is the premier source of organocatalysis and synthetic methods related information for chemists, biologists and engineers pursuing research in industry and academia.
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