Innovative Green Synthesis of 4-Aryl-Pyrazolo[5,6]Pyrano [2,3-<i>d</i>]Pyrimidines under Catalyst-Free Conditions

Ramesh, Rathinam; Tamilselvi, Velmurugan; Vadivel, Pullar; Lalitha, Appaswami

doi:10.1080/10406638.2018.1484780

Cited by 13 publications

(9 citation statements)

References 42 publications

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“…The novel pyrazolopyranopyrimidine 159 and its diverse analogues were synthesized under catalyst-free conditions. For this purpose, Bakherad and co-workers, 193 Kardooni and Kiasat, 186 and Rathinam et al 194 carried out a three-component equimolar reaction of 1 , 11 / 11a , 12c , and 28 under catalyst-free conditions in 4 mL of magnetized water at 50 °C, PEG-400 (3 mL) at RT, and 2 mL of aqueous EtOH at 80 °C ( Scheme 107 ). In Method 1, the magnetized water used here was prepared using a static magnetic system with a field strength of 6000 G with 500 mL s –1 for up to 10 min.…”

Section: Synthesis Of 5-aryl-substituted Pyrano[23- D ...mentioning

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: Synthesis Of 5-aryl-substituted Pyrano[23- D ...mentioning

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 Keggin-type catalyst activated oxygen atoms of carbonyl groups for condensation steps to construct pyrazole ring, Knoevenagel condensation of the aldehyde with barbituric acid, and pyran ring cyclization. 107 Keshavarz et al 110 have progressed a green protocol for the synthesis of the previously reported tricyclic systems 32, 104,108,[111][112][113] using a recyclable heterogeneous organicinorganic hybrid durable nano-catalyst "g-Al 2 O 3 @silane-TMG" (Scheme 21). Thus, four-component one-pot reactions of hydrazine, ethyl acetoacetate, (thio)barbituric acid, and aryl aldehydes in water under gently heating (40 C), and catalytic conditions gave the anticipated products 32 in 85-98% yields.…”

Section: Synthesis Of Tricyclic Systemsmentioning

confidence: 99%

“…Keshavarz et al 110 have progressed a green protocol for the synthesis of the previously reported tricyclic systems 32 , 104,108,111–113 using a recyclable heterogeneous organic-inorganic hybrid durable nano-catalyst “γ-Al 2 O 3 @silane-TMG” (Scheme 21). Thus, four-component one-pot reactions of hydrazine, ethyl acetoacetate, (thio)barbituric acid, and aryl aldehydes in water under gently heating (40 °C), and catalytic conditions gave the anticipated products 32 in 85–98% yields.…”

Section: Synthesis Of Tricyclic Systemsmentioning

confidence: 99%

Recent advancements in the multicomponent synthesis of heterocycles integrated with a pyrano[2,3-d]pyrimidine core

2022

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“…It involved innate benefits in using small organic molecules of biological origin as promoters, which are typically non‐toxic, insensitive to moisture and air, cost‐effective, easily available, efficient and selective . Organocatalyst corresponds to a low molecular weight organic molecule which in stoichiometric amounts catalyzes a chemical reaction . Bio‐organic catalysts are one of the organopromoter showing numerous excellent contributions in organic synthesis .…”

Section: Introductionmentioning

confidence: 96%

Organocatalyzed Domino Synthesis of New Thiazole‐Based Decahydroacridine‐1,8‐diones and Dihydropyrido[2,3‐d : 6,5‐d′]‐ dipyrimidines in Water as Antimicrobial Agents

Bhosle

Kharote

Bondle

et al. 2020

Chemistry & Biodiversity

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Organopromoter, 2‐aminoethanesulfonic acid was used to catalyze the synthesis of a series of structurally intriguing new hybrids thiazolyl acridine‐1,8(2H,5H)‐diones and dihydropyrido[2,3‐d : 6,5‐d′]dipyrimidine‐2,4,6,8(1H,3H,5H,7H)‐tetraones for the first time. 2‐Aminoethanesulfonic acid is a biobased organopromoter, used to generate four new bonds for the synthesis of new coupled thiazole‐based decahydroacridine‐1,8‐diones. Superior green credentials, operational simplicity, easy work‐up and recyclability of the catalyst are the key strengths of this method. The broad substrate scope, mild reaction conditions, short reaction time, cost effectiveness, high atom economy and good to excellent yields make the present method a distinct improvement over existing methods. Spectral (IR, 1H‐NMR,13C‐NMR, Mass) data and elemental analyses confirmed the structures of the titled products. A series of thiazolyl acridine‐1,8(2H,5H)‐diones and dihydropyrido[2,3‐d : 6,5‐d′]dipyrimidine‐2,4,6,8(1H,3H,5H,7H)‐tetraones were screened for their antimicrobial activity against four bacterial and three fungal strains.

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Innovative Green Synthesis of 4-Aryl-Pyrazolo[5,6]Pyrano [2,3-d]Pyrimidines under Catalyst-Free Conditions

Cited by 13 publications

References 42 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)

Recent advancements in the multicomponent synthesis of heterocycles integrated with a pyrano[2,3-d]pyrimidine core

Organocatalyzed Domino Synthesis of New Thiazole‐Based Decahydroacridine‐1,8‐diones and Dihydropyrido[2,3‐d : 6,5‐d′]‐ dipyrimidines in Water as Antimicrobial Agents

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