Unknown

Dataset Information

0

Quinazolin-4(3H)-ones and 5,6-Dihydropyrimidin-4(3H)-ones from ?-Aminoamides and Orthoesters.

ABSTRACT: Quinazolin-4(3H)-ones have been prepared in one step from 2-aminobenzamides and orthoesters in the presence of acetic acid. Simple 2-aminobenzamides were easily converted to the heterocycles by refluxing in absolute ethanol with 1.5 equivalents of the orthoester and 2 equivalents of acetic acid for 12?24 h. Ring-substituted and hindered 2-aminobenzamides as well as cases incorporating an additional basic nitrogen required pressure tube conditions with 3 equivalents each of the orthoester and acetic acid in ethanol at 110 °C for 12?72 h. The reaction was tolerant towards functionality on the benzamide and a range of structures was accessible. Workup involved removal of the solvent under vacuum and either recrystallization from ethanol or trituration with ether-pentane. Several 5,6-dihydropyrimidin-4(3H)-ones were also prepared from 3-amino-2,2-dimethylpropionamide. All products were characterized by melting point, FT-IR, ¹H-NMR, 13C-NMR, and HRMS.

SUBMITTER: Gavin JT 

PROVIDER: S-EPMC6278269 | biostudies-literature | 2018 Nov

REPOSITORIES: biostudies-literature

Json Xml
altmetric image

Publications

Quinazolin-4(3<i>H</i>)-ones and 5,6-Dihydropyrimidin-4(3<i>H</i>)-ones from β-Aminoamides and Orthoesters.

Gavin Joshua T JT   Annor-Gyamfi Joel K JK   Bunce Richard A RA  

Molecules (Basel, Switzerland) 20181109 11

Quinazolin-4(3<i>H</i>)-ones have been prepared in one step from 2-aminobenzamides and orthoesters in the presence of acetic acid. Simple 2-aminobenzamides were easily converted to the heterocycles by refluxing in absolute ethanol with 1.5 equivalents of the orthoester and 2 equivalents of acetic acid for 12⁻24 h. Ring-substituted and hindered 2-aminobenzamides as well as cases incorporating an additional basic nitrogen required pressure tube conditions with 3 equivalents each of the orthoester  ...[more]

Similar Datasets

Unknown Novel inhibitors of bacterial virulence: development of 5,6-dihydrobenzo[h]quinazolin-4(3H)-ones for the inhibition of group A streptococcal streptokinase expression.
| S-EPMC3605901 | biostudies-literature
Unknown 2-(5,6-Dihydro-benzimidazo[1,2-c]quinazolin-6-yl)phenol.
| S-EPMC3200611 | biostudies-literature
Unknown Synthesis of Quinazolin-4-ones by Copper-Catalyzed Isocyanide Insertion.
| S-EPMC7281788 | biostudies-literature
Unknown 2-(5,6-Dihydro-benzimidazo[1,2-c]quinazolin-6-yl)-5-methyl-phenol.
| S-EPMC3200579 | biostudies-literature
Unknown The PIFA-initiated oxidative cyclization of 2-(3-butenyl)quinazolin-4(3H)-ones - an efficient approach to 1-(hydroxymethyl)-2,3-dihydropyrrolo[1,2-a]quinazolin-5(1H)-ones.
| S-EPMC8630437 | biostudies-literature
Unknown 4H-Benzo[d][1,3]oxazin-4-ones and Dihydro Analogs from Substituted Anthranilic Acids and Orthoesters.
| S-EPMC6804250 | biostudies-literature
Unknown Primary Amine-Catalyzed Biginelli Reaction for the Enantioselective Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones.
| S-EPMC3008624 | biostudies-literature
Unknown The Synthesis and Evaluation of Dihydroquinazolin-4-ones and Quinazolin-4-ones as Thyroid Stimulating Hormone Receptor Agonists.
| S-EPMC3293179 | biostudies-literature
Unknown 2-(5,6-Di-hydro-benzimidazolo[1,2-c]quinazolin-6-yl)aniline methanol solvate.
| S-EPMC2969432 | biostudies-literature
Unknown 2-(5,6-Dihydro-benzimidazo[1,2-c]quinazolin-6-yl)-6-eth-oxy-phenol.
| S-EPMC3200659 | biostudies-literature