Selective bifunctionalization of pyrido[2,3-d]pyrimidines in positions 2 and 4 by SNAr and palladium-catalyzed coupling reactions

Acylation of 5-(2-ethoxyphenyl)-1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo [4,3-d) pyrimidin-7-one 1 with chloroacetylchloride in the presence of anyhydrous aluminium chloride affords 5-[(5-chloroacetyl-2-ethoxy)phenyl]-1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo [4,3-d] pyrimidin-7-one 2. The compound 2 condensed with various β-diketones/β-ketoesters compound, to obtain new β-diketones/ β-ketoesters 4a-i treated with ethylenediamine (EDA) gives 1H-1,4-diazepines. The compounds 5a-i has been screened for antimicrobial, antifungal and anthelmintic activities.

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“…They also find use in the treatment of impotence, one of male sexual dysfunction with the reduced side effects. 21 …”

Section: Introductionmentioning

confidence: 99%

Synthesis, antimicrobial and antifungal activities of novel 1H-1,4-diazepines containing pyrazolopyrimidinone moiety

Kumar

Joshi

2009

J Chem Sci

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“…[22,23] In general, the sulfanyl group can serve as a leaving group after oxidation to the corresponding sulfone for subsequent substitution with suitable nucleophiles. A thioether substituent, known to be inert under various conditions including S N Ar and certain cross-coupling reactions, was installed at the 6-position.…”

Section: Resultsmentioning

confidence: 99%

Palladium‐Catalyzed Amidation and Amination of 8‐Iodopurine

et al. 2012

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“…A sequential Suzuki coupling/amination reaction was recently described on 4,6‐dichloropyrimidines under microwave irradiation [13]. Some studies were also done on condensed halopyrimidines as for example on 2,4‐dichloropyridopyrimidines [14] or on 4‐chloro‐2‐trichloromethylquinazoline [15]. To the best of our knowledge, there is only one publication with one example on Suzuki coupling on 4‐chlorothieno[2,3‐ d ]pyrimidine [4a].…”

Section: Resultsmentioning

confidence: 99%

Unexpected CO bond formation in Suzuki coupling of 4‐chlorothieno[2,3‐d]pyrimidines

Perspicace¹,

Hesse²,

Kirsch³

et al. 2009

Journal of Heterocyclic Chem

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in Wiley InterScience (www.interscience.wiley.com).Palladium-catalyzed Suzuki reactions were performed on 4-chlorothieno [2,3-d]pyrimidines under classical heating conditions and under microwave irradiation. Some unexpected results were obtained during this study as two kinds of compounds were isolated depending on the conditions used. A careful investigation of experimental details has shown that the expected CAC bond formation occurred when degassed solvents were used (both in classical and microwave heating) whereas an unexpected CAO bond formation happened when solvents were not degassed with argon-bubbling before use.

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Selective bifunctionalization of pyrido[2,3-d]pyrimidines in positions 2 and 4 by SNAr and palladium-catalyzed coupling reactions

Cited by 25 publications

References 14 publications

Synthesis, antimicrobial and antifungal activities of novel 1H-1,4-diazepines containing pyrazolopyrimidinone moiety

Synthesis, antimicrobial and antifungal activities of novel 1H-1,4-diazepines containing pyrazolopyrimidinone moiety

Palladium‐Catalyzed Amidation and Amination of 8‐Iodopurine

Unexpected CO bond formation in Suzuki coupling of 4‐chlorothieno[2,3‐d]pyrimidines

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