Researches on Quinazolines (Twenty-First Paper). On Certain Quinazoline Oxygen Ethers of the Type —N:c(or)— And the Isomeric —NR.CO— Compounds.

Bogert, Marston Taylor; May, Clarence E.

doi:10.1021/ja01934a010

Cited by 21 publications

(11 citation statements)

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“…For the synthesis of quinazoline derivatives, see: Bogert & May (1909); Smith et al (2005) Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and CHEMDRAW Ultra (Cambridge Soft, 2001).…”

Section: Related Literaturementioning

confidence: 99%

“…For ring substitution and modification of 4-methoxyquinazolines, see: Smith et al (2005). 4-Methoxyquinazoline was synthesized in 81% yield from reaction of quinazoline-4(3H)-thione with iodomethane in aqueous methanol containing potassium hydroxide at room temperature for 24 h (Bogert & May, 1909). The asymmetric unit consists of one molecule of C 9 H 8 N 2 O (Fig.…”

Section: S1 Structural Commentarymentioning

confidence: 99%

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Crystal structure of 4-methoxyquinazoline

et al. 2014

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Section: Related Literaturementioning

confidence: 99%

Section: S1 Structural Commentarymentioning

confidence: 99%

Crystal structure of 4-methoxyquinazoline

et al. 2014

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“…4-(Methylthio)quinazoline (7), 4-(ethylthio)quinazoline (8) and 4-methoxyquinazoline (9) were all prepared according to literature procedures [37][38][39][40]. It was found that reactions of compounds 7-9 with alkyllithiums (t-BuLi, n-BuLi, MeLi) occurred smoothly and rapidly at -78 C in dry THF.…”

Section: Resultsmentioning

confidence: 99%

Addition of alkyllithiums to 3H-quinazoline-4-thione and various substituted quinazoline derivatives; application in synthesis

Smith

El‐Hiti

Hegazy

2005

Journal of Sulfur Chemistry

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Reaction of 3H-quinazoline-4-thione (1) with two mole equivalents of an alkyllithium (t-BuLi, n-BuLi or MeLi) at -78 C in dry THF gave the corresponding 2-alkyl-1,2-dihydro-3H-quinazoline-4-thione (4, 5 or 6) in high yield. Similarly, reactions of 4-(methylthio)quinazoline (7), 4-(ethylthio)quinazoline (8) and 4-methoxyquinazoline (9) with alkyllithiums (one mole equivalent) gave the corresponding 4-substitued 2-alkyl-1,2-dihydroquinazolines 11-18. On the other hand, blocking position 2 with a phenyl group in 4-(methylthio)-2-phenylquinazoline (20) and 4-methoxy-2-phenylquinazoline (21) resulted in reaction with two mole equivalents of alkyllithiums to give 4,4-dialkyl-2-phenyl-3,4-dihydroquinazolines 22-24.

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“…Therefore, the degradation of quinazolinone by simple chemical oxidation has not been reported. However, treatment of phosphorous pentachloride leads to the formation of a 4‐chloroquinazoline‐substitution product [9].…”

Section: Reactivity and Aromaticity Of 4(3h)‐quinazolinones Ring Systemmentioning

confidence: 99%

Medicinal perspective of quinazolinone derivatives: Recent developments and structure–activity relationship studies

Wahan

Sharma

Chawla

2021

Journal of Heterocyclic Chem

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Heterocyclic rings have long piqued the interest of medicinal chemists. Quinazolinone is a fused nitrogen‐based heterocyclic moiety. Some of quinazolinone derivatives have emerged as marketed drugs. A tremendous number of pharmacological activities such as anticancer, anticonvulsant, antimalarial, antifungal, antibacterial, antiinflammatory, MMP inhibitors, antidiabetic, antileishmanial, and hypolipidemic properties have been explored. A number of quinazolinone derivatives have already paved way in various stages of clinical trials. An extensive literature on developed synthetic schemes based on green chemistry and biological activities of quinazolinone has been included in this study. The content of patent filed and granted of various quinazolinone‐based compounds are also mentioned.

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Researches on Quinazolines (Twenty-First Paper). On Certain Quinazoline Oxygen Ethers of the Type —N:c(or)— And the Isomeric —NR.CO— Compounds.

Cited by 21 publications

References 0 publications

Crystal structure of 4-methoxyquinazoline

Crystal structure of 4-methoxyquinazoline

Addition of alkyllithiums to 3H-quinazoline-4-thione and various substituted quinazoline derivatives; application in synthesis

Medicinal perspective of quinazolinone derivatives: Recent developments and structure–activity relationship studies

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