Benzyltrimethylammoniumfluoride Hydrate: An Efficient Catalyst for One-Pot Synthesis of Hantzsch 1,4-Dihydropyridines and Their Aromatization

Khaskel, Anamika; Barman, Pranjit

doi:10.1002/hc.21308

Cited by 6 publications

(2 citation statements)

References 32 publications

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“…Almost around the same time, Khaskel and Barman demonstrated the use of Benzyl trimethyl ammonium fluoride Hydrate (BTMAFH) as an effective catalyst for the construction of 1,4‐dihydropyridines 10 from the domino four‐component reaction of 1 equivalent of aldehydes 1 , 2 equivalent of 1,3‐diketones 8 , and 1 equivalent of ammonium acetate 3 in absence of any solvents (Scheme 17). [38] The reaction required only 10 mol% of BTMAFH as the efficient loading for affording the respective products in 83–93 % yield. Initially, the reaction was performed by changing the halogenated groups (fluoride, chloride, bromide) of the catalyst; among them, the fluoride substituent was found to be more efficient than their corresponding chloride, bromide, and iodide due to their smaller size and high electronegativity thereby making it more likely to abstract active hydrogen from β‐ketoesters.…”

Section: Synthesis Of 14‐dihydropyridines Via One‐pot Reactions Under...mentioning

confidence: 99%

Recent Advances and Prospects in the Transition‐Metal‐Free Synthesis of 1,4‐Dihydropyridines

et al. 2022

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The synthesis of novel nitrogen‐containing heterocycles as a result of their frequent existence in natural products, commercially available drugs, and optoelectronic materials is extremely demanding but challenging due to the involvement of toxic solvents, and sometimes transition‐metal catalyst(s) which are often associated with environmental safety concerns. 1,4‐dihydropyridine (1,4‐DHP), of synthetic and natural origin, are among one of the privileged classes of nitrogen‐containing heterocycles, representing a broad spectrum of pharmaceutical properties, and has received considerable interest in medicinal and synthetic organic chemistry. Recognizing the prominent significance of this structural motif, substantial efforts have been paid not only for their expedient synthesis but also for the discovery of novel complex molecules by using them as key active building blocks. However, developing elegant synthetic processes provides effortless access to 1,4‐dihydropyridines by exploring environmentally friendly conditions with the primary goal of lowering the expenditure of the overall process is extremely demanding but challenging. In this mini‐review article, we have demonstrated a clear presentation of the recent transition‐metal‐free catalyzed synthesis of 1,4‐dihydropyridines of potential therapeutic interests and covered the literature from 2015 to date.

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Section: Synthesis Of 14‐dihydropyridines Via One‐pot Reactions Under...mentioning

confidence: 99%

Recent Advances and Prospects in the Transition‐Metal‐Free Synthesis of 1,4‐Dihydropyridines

et al. 2022

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“…2010 年, Khan 等 [70] 以 10 mol%的 TBAB 催化芳胺作为氮源的 Hantzsch 反应, 在乙醇中 8～30 min 合成了目标化合物. 而 Khaskel 等 [71] 在 2016 年以 10 mol%的三甲基苄基氟化铵水合物(BTMAFH)为催化剂, 在无溶剂的条件下合成对称结构的 1,4-DHPs (Eq. 12), 在反应体系中加入 K 2 S 2 O 8 可以使产物大于 90%的产率芳香化.…”

Section: 其他绿色催化unclassified

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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ChemInform Abstract: Benzyltrimethylammoniumfluoride Hydrate: An Efficient Catalyst for One‐Pot Synthesis of Hantzsch 1,4‐Dihydropyridines and Their Aromatization.

Khaskel

Barman

2016

ChemInform

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Benzyltrimethylammoniumfluoride Hydrate: An Efficient Catalyst for One-Pot Synthesis of Hantzsch 1,4-Dihydropyridines and Their Aromatization

Cited by 6 publications

References 32 publications

Recent Advances and Prospects in the Transition‐Metal‐Free Synthesis of 1,4‐Dihydropyridines

Recent Advances and Prospects in the Transition‐Metal‐Free Synthesis of 1,4‐Dihydropyridines

Progress in Synthesis of 1,4-Dihydropyridines

ChemInform Abstract: Benzyltrimethylammoniumfluoride Hydrate: An Efficient Catalyst for One‐Pot Synthesis of Hantzsch 1,4‐Dihydropyridines and Their Aromatization.

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