ZrCl4-catalyzed one-pot multi-component synthesis of hexahydropyrano pyrimidinone derivatives

Pisal, Parshuram M.; Sawant, Ajay S.; Kamble, Vinod T.; Varala, Ravi; Adil, Syed Farooq; Khan, Mujeeb; Siddiqui, Mohammed Rafiq H.

doi:10.25135/acg.oc.72.20.02.1551

Cited by 3 publications

(2 citation statements)

References 24 publications

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“…The major advantages of this reaction protocol are the use of inexpensive SbCl 3 catalyst and ethanol as a nontoxic solvent. Recently, Pisal et al 32 synthesized analogues of compound 4, i.e., 4f, by using the same substrate scope in ethanol under reflux for 2−3 h as shown in the previous reaction. However, in this case, instead of antimony trichloride they used zirconium tetrachloride as the Lewis acid catalyst (Scheme 7).…”

Section: Metal Catalystmentioning

confidence: 99%

Importance of Hybrid Catalysts toward the Synthesis of 5H-Pyrano[2,3-d]pyrimidine-2-ones/2,4-diones (Thiones)

2023

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The pyranopyrimidine core is a key precursor for medicinal and pharmaceutical industries due to its broader synthetic applications as well as its bioavailability. Among its four possible isomers, we found that 5H-pyrano[2,3-d]pyrimidine scaffolds have a wide range of applicability, and in recent years, they have been intensively investigated, but the development of the main core is found to be more challenging due to its structural existence. In this review article, we cover all of the synthetic pathways that are employed for the development of substituted 4-aryl-octahydropyrano/hexahydrofuro[2,3-d]pyrimidin-2-one (thiones) and 5-aryl-substituted pyrano[2,3-d]pyrimidindione (2-thiones) derivatives through a one-pot multicomponent reaction using diversified hybrid catalysts such as organocatalysts, metal catalysts, ionic liquid catalysts, nanocatalysts, green solvents, catalyst-/solvent-free conditions, and miscellaneous catalysts as well as the mechanism and recyclability of the catalysts. This review mainly focuses on the application of hybrid catalysts (from 1992 to 2022) for the synthesis of 5H-pyrano[2,3-d]pyrimidine scaffolds. This review will definitely attract the world’s leading researchers to utilize broader catalytic applications for the development of lead molecules.

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Section: Metal Catalystmentioning

confidence: 99%

Importance of Hybrid Catalysts toward the Synthesis of 5H-Pyrano[2,3-d]pyrimidine-2-ones/2,4-diones (Thiones)

2023

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“…From the last two decades synthesis of dihydropyrimidine-2(1H) one and their derivatives being ainteresting field of research because it have wide spectrum and useful building blocks for designing new compounds with ample of biological and pharmacological application 3,7 . Synthesis of dihydropyrimidine-2(1H) oneand their analogue is increasing tremendously in passes few years.The dihydropyrimidine-2(1H) one and their derivatives have attracted great attention recently in synthetic organic chemistry as it is widely used in the field of drug research as related medical chemistry is an applied science with fundamental roots originated from all branch of chemistry 8 . The term of medical chemistry where the corresponding of drugs to materials useful in pharmacy the term of pharmaceutical science in chemical synthesis as they have been associated with diverse range therapeutic and medical properties 9,10 .…”

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confidence: 99%

Synthesis, Characterization and Biological Evaluation of 6-(5-Chloro-8-Hydroxynapthalene-2-yl)-4(4-Hydroxyphenyl)-4-5-Dihydroxypyrimidin-2(1h)-One

-¹,

-²,

-³

2022

IJFMR

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1-(4- Chloro -1-hydroxynaphthalen-2-yl)-ethanone was prepared by refluxing 4-chloronaphthalen-1-ol with glacial acetic acid in presence of fused ZnCl2. From this synthesized compound we prepared 1-(4- Chloro -1- hydroxynaphthalen-2-yl)-3-(4-hydroxy phenyl)-prop-2-en-1-one from condensing 1-(4- Chloro -1-hydroxynaphthalen-2- yl)-ethenone, The final product 6-(5-chloro-8-hydroxynapthalene-2-yl)-4(4-hydroxyphenyl)-4-5-dihydroxypyrimidin-2(1h)-one, by condensation in presence of urea and concentrated HCl in DMF. The compounds thus synthesized have been characterized by physical and spectral data. This titled synthesized compound was screened for antimicrobial study and are found to possess excellent antimicrobial activities due to presence of chlorine as a substituent on main nucleus.

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Zirconium Tetrachloride

Gundersen,

Rise,

Undheim

et al. 2024

Encyclopedia of Reagents for Organic Synthesis

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image [ 10026‐11‐6 ] Cl 4 Zr (MW 233.02) InChI = 1S/4ClH.Zr/h4*1H;/q;;;;+4/p‐4 InChIKey = DUNKXUFBGCUVQW‐UHFFFAOYSA‐J (Lewis acid) Physical Data : subl. 331 °C, mp 437 °C/25 atm; d 2.803 g cm −3 . Solubility : sol alcohol, ether. Form Supplied in : white solid; widely available. Purification : crystallize repeatedly from conc hydrochloric acid. Handling, Storage, and Precautions : extremely hygroscopic; decomposed by water to ZrOCl 2 and HCl. Reagent causes burns, and is harmful if inhaled or swallowed or if it comes in contact with skin. It is stable at high temperatures under N 2 , H 2 , or O 2 . Use in a fume hood.

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ZrCl4-catalyzed one-pot multi-component synthesis of hexahydropyrano pyrimidinone derivatives

Cited by 3 publications

References 24 publications

Importance of Hybrid Catalysts toward the Synthesis of 5H-Pyrano[2,3-d]pyrimidine-2-ones/2,4-diones (Thiones)

Importance of Hybrid Catalysts toward the Synthesis of 5H-Pyrano[2,3-d]pyrimidine-2-ones/2,4-diones (Thiones)

Synthesis, Characterization and Biological Evaluation of 6-(5-Chloro-8-Hydroxynapthalene-2-yl)-4(4-Hydroxyphenyl)-4-5-Dihydroxypyrimidin-2(1h)-One

Zirconium Tetrachloride

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