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An Organocatalytic Cascade Synthesis of Diverse 1H-Pyrazolo[1,2-b]phthalazine-2-carboxamide,1H-Pyrazolo[1,2-b]phthalazine, 4H-Pyrano[2,3-c]pyrazole and 4H-Benzo[g]chromenes via Multicomponent Reactions
Organic Preparations and Procedures International ( IF 1.5 ) Pub Date : 2020-01-02 , DOI: 10.1080/00304948.2019.1693241
Cinnathambi Subramani Maheswari 1 , Velmurugan Tamilselvi 1 , Rathinam Ramesh 1 , Appaswami Lalitha 1
Affiliation  

We now demonstrate a one-pot syntheses of the title compounds using 2-aminopyridine (2-AP) as a reusable organocatalyst. Generally, nitrogen and oxygen containing heterocyclic compounds perform crucial roles in the pharmaceutical and agricultural industries. Phthalazine bearing compounds with bridgehead nitrogen have significant pharmacological applications. In addition, their luminescence and fluorescence properties have been productively investigated. The synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives via the three component cyclocondensation reaction of aromatic aldehydes, phthalhydrazide, malononitrile/ethyl cyanoacetate has been achieved by using various catalysts such as [Bmim]OH, PTSA/BmimBr, Et3N/EtOH, 11 NaHCO3, 12 nano-ZnO, NaBr, saccharin, Fe3O4, 16 CAN and PEG-SAC. The literature reports show their intrinsic advantages and disadvantages. Most of the reported protocols employed active cyanomethylene reagents, such as malononitrile and ethyl cyanoacetate, for the synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives. Cyanoacetamide is one of the active methylene compounds which has been extensively used in heterocyclic synthesis. This motivated us to use it as the active methylene reagent for the preparation of 3-amino-1H-pyrazolo[1,2-b]phthalazine-2carboxamide derivatives. Similarly, the pyrazole templates have a broad range of medicinal applications. Indeed, some pyrazole-containing molecules, such as celecoxib, viagra and pyrazofurine, are blockbuster drugs of the pharmaceutical industries. The pyranopyrazole motifs are highly desirable heterocyclic compounds which exhibit significant biological activities such as antimicrobial, anti-inflammatory, anticancer, insecticidal and molluscicidal properties. In recent decades, the four component reaction of hydrazine hydrate, ethyl acetoacetate, malononitrile and aldehyde has been successful for the synthesis of pyranopyrazoles using different catalysts. 2-Amino-4H-benzo[g]chromene derivatives also show excellent biological activities. Hydroxy substituted naphthalene-1,4-dione derivatives are used as fluorescent

中文翻译:

多种1H-吡唑并[1,2-b]酞嗪-2-甲酰胺、1H-吡唑并[1,2-b]酞嗪、4H-吡喃并[2,3-c]吡唑和4H-苯并[的有机催化级联合成g]色烯通过多组分反应

我们现在展示了使用 2-氨基吡啶 (2-AP) 作为可重复使用的有机催化剂的标题化合物的一锅法合成。通常,含氮和氧的杂环化合物在制药和农业行业中发挥着至关重要的作用。带有桥头氮的含酞嗪化合物具有重要的药理学应用。此外,已对它们的发光和荧光特性进行了富有成效的研究。1H-吡唑并[1,2-b]酞嗪-5,10-二酮衍生物通过芳醛、邻苯二甲酰肼、丙二腈/氰基乙酸乙酯三组分环缩合反应合成1H-吡唑并[1,2-b]酞嗪-5,10-二酮衍生物已通过使用多种催化剂如[Bmim]OH实现, PTSA/BmimBr, Et3N/EtOH, 11 NaHCO3, 12 nano-ZnO, NaBr, 糖精, Fe3O4, 16 CAN 和 PEG-SAC。文献报道显示了它们的内在优势和劣势。大多数报道的协议采用活性氰基亚甲基试剂,如丙二腈和氰基乙酸乙酯,用于合成 1H-吡唑并 [1,2-b] 酞嗪-5,10-二酮衍生物。氰基乙酰胺是一种活性亚甲基化合物,广泛用于杂环合成。这促使我们将其用作制备 3-氨基-1H-吡唑并[1,2-b]酞嗪-2甲酰胺衍生物的活性亚甲基试剂。类似地,吡唑模板具有广泛的医药应用。事实上,一些含吡唑的分子,如塞来昔布、伟哥和吡唑啉,是制药行业的重磅药物。吡喃并吡唑基序是非常理想的杂环化合物,其表现出显着的生物活性,例如抗微生物、抗炎、抗癌、杀虫和杀软体动物的特性。近几十年来,水合肼、乙酰乙酸乙酯、丙二腈和醛的四组分反应已成功用于使用不同催化剂合成吡喃并吡唑。2-氨基-4H-苯并[g]色烯衍生物也表现出优异的生物活性。羟基取代的萘-1,4-二酮衍生物用作荧光剂 丙二腈和醛已成功用于使用不同催化剂合成吡喃并吡唑。2-氨基-4H-苯并[g]色烯衍生物也表现出优异的生物活性。羟基取代的萘-1,4-二酮衍生物用作荧光剂 丙二腈和醛已成功用于使用不同催化剂合成吡喃并吡唑。2-氨基-4H-苯并[g]色烯衍生物也表现出优异的生物活性。羟基取代的萘-1,4-二酮衍生物用作荧光剂
更新日期:2020-01-02
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