Catalyst free, one-pot, facile synthesis of novel pyrazolo-1,4-dihydropyridine derivative form pyranopyrazoles

Sohal, Harvinder Singh; Goyal, Arun; Khare, Rajshree; Singh, Kawaljeet; Sharma, Rajeev Kr.

doi:10.5155/eurjchem.5.2.227-232.967

Eur. J. Chem.

2014

DOI: 10.5155/eurjchem.5.2.227-232.967

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Catalyst free, one-pot, facile synthesis of novel pyrazolo-1,4-dihydropyridine derivative form pyranopyrazoles

Harvinder Singh Sohal

Arun Goyal

Rajshree Khare

et al.

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Cited by 2 publications

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“…1.1.2 多元醇及其聚合物多元醇及其聚合物, 包括乙二醇(EG)、甘油和低聚乙二醇(PEG-200 到 PEG-600)作为有机合成反应的溶剂, 具有低毒性、生物可降解、沸点高、低蒸汽压和对极性物质溶解能力强等特点 [24] , 可作为助溶剂、乳化剂、稳定剂、相转移催化剂和表面活性剂等. 近些年, 该类溶剂已越来越广泛地运用于各种有机反应, 如 Heck 和 Suzuki 偶联 [25] 、Michael 加成 [26] 、Fridel-Crafts 加成和环氧开环等 [27] , 也在 Hantzsch 反应中进行应用.…”

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Progress in Synthesis of 1,4-Dihydropyridines

Lingling,

Hui,

Pan

et al. 2016

Chinese Journal of Organic Chemistry

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1,4-Dihydropyridines (1,4-DHPs) are an important class of heterocyclic compounds, and possess a broad array of biological activities and applications. With the development of green organic synthetic chemistry, some important achievements have been made in the green synthesis of 1,4-DHPs and new synthetic methods, which made up some shortcomings of the traditional synthesis of Hantzch reaction, such as environment friendly, synthesis efficiency, single product structure and lack of reaction type. This review provides the first overview for the green synthesis of Hantzch reaction and new synthetic methods of 1,4-DHPs since 2010. A comprehensive and up-to-date introduction are given for Hantzch reaction under geen solvent, geen catalyst and geen synthetic technology, and the new reaction of synthesis of 1,4-DHPs based on new building blocks. A thorough analysis is provided concerning the feature of improvement of green synthesis of Hantzsch reaction and new synthetic method. Moreover, the substrates, conditions, selectivities and yields have been also described. Finally, a brief discussion relating to developments and potential areas of further research concerning new synthetic methods of 1,4-DHPs and green synthesis, and chiral synthesis, is presented. Keywords 1,4-dihydropyridines; Hantzsch reaction; clean synthesis; enaminone 1,4-二氢吡啶(1,4-DHPs)是一类重要的含氮杂环化合物, 具有广泛的生理活性和应用价值. 其中最重要的是临床上作为钙离子通道阻滞剂治疗心脑血管和高血压等疾病 [1] , 例如, 尼卡地平(Nicardipine, 1)、尼莫地平 (Nimodipine, 2)、尼非地平(Nifedipine, 3)和非洛地平 (Felodipine, 4)等. 作为药物或药物中间体它们还具有抗人类免疫缺陷病毒(HIV) [1c,2] 、抗菌 [3] 、抗惊厥 [4] 、抗肿瘤(化合物 5) [5] 、神经保护 [6] 、辐射防护 [7] 等生物活性 [8] , 可用于合成各种各样含氮杂环化合物 [9] . 在合成中, 可作为氢源应用于众多的有机还原反应(如 Hantzsch 酯, 6) [10] (图 1). 因此, 对 1,4-DHPs 的研究十分活跃, 一直以来受到科研工作者的广泛关注.1,4-DHPs 的传统合成策略是 Hantzsch 反应的"一锅法" 合成, 于 1881 年 Hantzsch [11] 最早报道的两分子 β-羰基酸酯、一分子醛和一分子氨发生缩合反应得到 (Scheme 1). 反应经一分子 β-羰基酸酯和醛反应生成 α,β-不饱和化合物, 与另一分子 β-羰基酸酯和氨反应生成的 β-胺基烯酸酯发生 Micheal 加成反应, 再脱去一分

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Progress in Synthesis of 1,4-Dihydropyridines

Lingling,

Hui,

Pan

et al. 2016

Chinese Journal of Organic Chemistry

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Synthesis and Antimicrobial Evaluation of Some Novel 2-[4-Substituted 5-(ethoxycarbonyl)-3-methyl-1,4-dihydropyrano[2,3-c]pyrazol-6-yl]acetic Acid Derivatives

et al. 2023

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Catalyst free, one-pot, facile synthesis of novel pyrazolo-1,4-dihydropyridine derivative form pyranopyrazoles

Cited by 2 publications

References 15 publications

Progress in Synthesis of 1,4-Dihydropyridines

Progress in Synthesis of 1,4-Dihydropyridines

Synthesis and Antimicrobial Evaluation of Some Novel 2-[4-Substituted 5-(ethoxycarbonyl)-3-methyl-1,4-dihydropyrano[2,3-c]pyrazol-6-yl]acetic Acid Derivatives

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