Synthesis of new annulated pyrano[2,3-d]pyrimidine derivatives using organo catalyst (DABCO) in aqueous media

Bhat, Ajmal R.; Shalla, Aabid H.; Dongre, Rajendra S.

doi:10.1016/j.jscs.2014.03.008

Cited by 42 publications

(22 citation statements)

References 24 publications

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“…After immense literature survey, it was found that catalyst free synthesis of pyrido[2,3‐ d ]pyrimidine has not been reported till date . Thus to carry onward our research program of designing green synthetic strategies to important heterocyclic molecules, we herein report a new, metal free, clean and efficient one‐pot synthesis of Pyrano[2,3‐ d ]pyrimidine using ethylene glycol as a promoting medium (Scheme ).…”

Section: Introductionmentioning

confidence: 99%

A Green Access to Tetrahydro-1H-pyrano[2,3-d]pyrimidines: Visible-Light-Triggered and Ethylene-Glycol-Mediated Multicomponent One-Pot Process.

et al. 2017

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Efficient and environmentally benign heterocyclization via Knoevenagel condensation followed by [4 + 2] cycloaddition resulting the synthesis of tetrahydro-1H-pyrano[2,3-d]pyrimidine derivatives starting from 2-thiobarbutiric acid, aldehydes and alkyne has been reported. Easily available ethylene glycol was used as a green promoting medium as well as solvent for the reaction progress. This methodology offers a metal and base free approach which endowed high yields with mild reaction conditions and better functional group tolerating ability. Further visible light as a source of energy, recyclability and reuse of ethylene glycol add the methodology a wide scope.

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Section: Introductionmentioning

confidence: 99%

A Green Access to Tetrahydro-1H-pyrano[2,3-d]pyrimidines: Visible-Light-Triggered and Ethylene-Glycol-Mediated Multicomponent One-Pot Process.

et al. 2017

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“…Plausible mechanisms for the reaction are provided in Bhat et al and Jain et al; however, these mechanisms are either unclear or have missing steps. A more comprehensive mechanism is presented in Figure , involving formation of an arylidene intermediate, which is subject to a Michael reaction by barbituric acid.…”

Section: Resultsmentioning

confidence: 99%

“…By reacting ethyl 2‐cyanoacetate with barbituric acid and substituted benzaldehydes in the presence of DABCO, an ethyl ester group was placed at C‐6 instead of the nitrile group . Pyrano[2,3‐ d ]pyrimidines with phenyl groups at both positions 5 and 7 were synthesized by the reaction of chalcones with barbituric acid in the presence of acetic acid and P 2 O 5 as a catalyst…”

Section: Introductionmentioning

confidence: 99%

Synthesis of chloro, fluoro, and nitro derivatives of 7‐amino‐5‐aryl‐6‐cyano‐5H‐pyrano pyrimidin‐2,4‐diones using organic catalysts and their antimicrobial and anticancer activities

Aremu

Singh

et al. 2019

Journal of Heterocyclic Chem

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Chloro, fluoro, and nitro derivatives of 7‐amino‐5‐aryl‐6‐cyano‐5H‐pyrano pyrimidin‐2,4‐diones were produced by reacting malononitrile, barbituric acid, and aromatic aldehydes together with a DABCO catalyst in an aqueous one‐pot reaction. This is the first report of these compounds being synthesized with DABCO as a catalyst, which produced the compounds in yields in excess of 90%. The 2,4‐difluoro derivative (11) was novel. The structures of the synthesized compounds were elucidated by means of 1H, 13C, and 2D NMR spectroscopy. Compound 2 (2‐Cl derivative) had MBC values of <200μM against both Staphylococcus aureus and MRSA, and the 2‐nitro derivative 5 had an MBC of 191μM against the Gram–ve Escherichia coli. The synthesized compounds were also tested for their anticancer activity against a HeLa cell line, where all the compounds showed better activity (IC50 values between 129μM and 340μM) than 5‐fluorouracil, a commonly known anticancer drug.

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“…In continuation of the current research from our laboratory to develop an efficient multicomponent reactions (MCRs) for the preparation of pyrimidine annulated bioactive molecules [30], we report here, the dibutylamine ( …”

Section: Introductionmentioning

confidence: 99%

Dibutylamine (DBA): A highly efficient catalyst for the synthesis of pyrano[2,3-d]pyrimidine derivatives in aqueous media

Bhat

Shalla

Dongre

2016

Journal of Taibah University for Science

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Annulated pyrano [2,3-d]pyrimidine derivatives were synthesized via one-pot three component condensation reactions of various aromatic aldehydes, malononitrile and barbituric acid in aqueous ethanol using dibutylamine (DBA) as catalyst. The potential application of DBA in organic synthesis increasing rapidly due to its reaction simplicity, minimum reaction time, high yields of the desired products (83-94%) and low cost chemicals. All the synthesized pyrano[2,3-d] pyrimidine derivatives were characterized by IR, 1 H NMR, 13 C NMR and mass spectra.

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Synthesis of new annulated pyrano[2,3-d]pyrimidine derivatives using organo catalyst (DABCO) in aqueous media

Cited by 42 publications

References 24 publications

A Green Access to Tetrahydro-1H-pyrano[2,3-d]pyrimidines: Visible-Light-Triggered and Ethylene-Glycol-Mediated Multicomponent One-Pot Process.

A Green Access to Tetrahydro-1H-pyrano[2,3-d]pyrimidines: Visible-Light-Triggered and Ethylene-Glycol-Mediated Multicomponent One-Pot Process.

Synthesis of chloro, fluoro, and nitro derivatives of 7‐amino‐5‐aryl‐6‐cyano‐5H‐pyrano pyrimidin‐2,4‐diones using organic catalysts and their antimicrobial and anticancer activities

Dibutylamine (DBA): A highly efficient catalyst for the synthesis of pyrano[2,3-d]pyrimidine derivatives in aqueous media

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