Efficient Niementowski synthesis of novel derivatives of 1,2,9,11-tetrasubstituted-7H-thieno[2',3':4,5]pyrimido[6,1-b]-quinazolin-7-one

Laddha, Sachin S.; BHATNAGAR, S. P.

doi:10.3998/ark.5550190.0009.h20

Cited by 4 publications

(3 citation statements)

References 13 publications

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“…The products 115a–o were formed through nucleophilic attack of the amino group of the anthranilic acids at C4 of thieno[2,3- d ]pyrimidines 113a–e, followed by 1,3 proton transfer and subsequent intramolecular cyclocondensation ( Scheme 27 ). 96 …”

Section: Synthetic Methodsmentioning

confidence: 99%

“…The products 115a-o were formed through nucleophilic attack of the amino group of the anthranilic acids at C4 of thieno [2,3-d] pyrimidines 113a-e, followed by 1,3 proton transfer and subsequent intramolecular cyclocondensation (Scheme 27). 96 As well, pyridopyrimidinones 117a-g were synthesized by reuxing 2-amino-nicotinonitriles 116a-g in formic acid. Niementowski condensation of 117a-g with anthranilic acids 118ac under microwave irradiation conditions, by reuxing in the presence of polyphosphoric acid, or by the direct fusion method yielded the anticipated 8H-pyridopyrimidoquinazolinones 119a-u.…”

Section: Synthesis Of Tetracyclic Systemsmentioning

confidence: 99%

“…Two series of thienopyrimidoquinazolinones 115a-o and pyridopyrimidoquinazolinones 119a-u (Schemes 27 and 28 and Fig. 3) 92,96 were assessed as anticonvulsant agents (anti-MES and anti-scPTZ). The compounds showed potent activities.…”

Section: Anticonvulsant Activitymentioning

confidence: 99%

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Advances in the chemical and biological diversity of heterocyclic systems incorporating pyrimido[1,6-a]pyrimidine and pyrimido[1,6-c]pyrimidine scaffolds

et al. 2020

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Section: Synthetic Methodsmentioning

confidence: 99%

Section: Synthesis Of Tetracyclic Systemsmentioning

confidence: 99%

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Advances in the chemical and biological diversity of heterocyclic systems incorporating pyrimido[1,6-a]pyrimidine and pyrimido[1,6-c]pyrimidine scaffolds

et al. 2020

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Synthesis, Characterization and Biological Evaluation of some New Thieno[2,3-d]Pyrimidine Derivatives

El-mahdy

El-Kazak

Abdel-Megid

et al. 2009

JAC

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10-Oxo-4,6,7,8,9,10-hexahydroprazolo[1,5-a][1]benzothieno[2,3-d]pyrimidine-3-carbaldehyde (2) was prepared by Vilsmeier-Haack reaction of 3-amino-2-methyl-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidin-4(3H)-one (1). Reaction of carbaldehyde derivative 2 with malononitrile afforded arylidene malononitrile 3. Cyclization of the latter compound with thiourea yielded pyrimidinethione 4. Interaction of carbaldehyde derivative 2 in presence of thiourea with keto- compounds such as ethyl acetoacetate, or acetylacetone, or dimedone or ethyl cyanoacetate gave pyrimidine derivatives 5-8. Hydrazinolysis of carbaldehyde derivative 2 gave the hydrazone 9. Reaction of the latter with phenyl isothiocyanate afforded thiosemicarbazone 10, which underwent cyclization with oxalyl chloride to give thioxoimidazolidinedione 11. Condensation of compound 2 with thiosemicarbazide furnished thiosemicarbazone derivative 12. Reaction of compound 2 with aminopyrazolone in the presence of an acid and/or a base afforded pyrazolones 13 and 14. Treatment of carbaldehyde derivative 2 with cyanoacetohydrazide gave acrylohydrazide 15. Interaction of the latter with carbon disulfide yielded mercaptooxadiazole 16. Condensation of compound 2 with acetylpyridazinone 17 produced chalcone 18. Reaction of compound 18 with malononitrile in pyridine gave cyanopyran 19, while its reaction with malononitrile in presence of ammonium acetate in ethanol yielded cyanopyridine 20. Structures of the newly synthesized products have been deduced on the basis of elemental analysis and spectral data. The synthesized compounds were screened for their antimicrobial activity.

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The Synergy of Combined Use of DMSO and Bronsted Acid (Ionic Liquid) as a Catalyst Part I: Efficient Niementowski Synthesis of Modified Quinazolinones

Kathiravan¹,

Jalnapurkar²,

Chitre³

et al. 2011

GSC

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A new rapid and versatile approach using Ionic liquid/DMSO as a chemical reagent for the synthesis of fused heterocyclic compounds in a highly efficient way is described. This method offers the advantages of proceeding in neutral conditions, giving high to excellent isolated yields (83–92%) for Niementowski synthesis with easy workup procedure. The inherent Bronsted acidity of ionic liquid and high polarity of both IL and DMSO resulted in a significant enhancement in the reaction rate

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Efficient Niementowski synthesis of novel derivatives of 1,2,9,11-tetrasubstituted-7H-thieno[2',3':4,5]pyrimido[6,1-b]-quinazolin-7-one

Cited by 4 publications

References 13 publications

Advances in the chemical and biological diversity of heterocyclic systems incorporating pyrimido[1,6-a]pyrimidine and pyrimido[1,6-c]pyrimidine scaffolds

Advances in the chemical and biological diversity of heterocyclic systems incorporating pyrimido[1,6-a]pyrimidine and pyrimido[1,6-c]pyrimidine scaffolds

Synthesis, Characterization and Biological Evaluation of some New Thieno[2,3-d]Pyrimidine Derivatives

The Synergy of Combined Use of DMSO and Bronsted Acid (Ionic Liquid) as a Catalyst Part I: Efficient Niementowski Synthesis of Modified Quinazolinones

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