THE SYNTHESIS OF 2-METHYL-5-NITRO-4-KETODIHYDROQUINAZOLINES FROM 6-NITROACETANTHRANIL AND PRIMARY AMINES.<sup>1</sup>

Bogert, Marston Taylor; Seil, Harvey Ambrose

doi:10.1021/ja01988a014

Cited by 11 publications

(1 citation statement)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Synthesis of the title compounds 5a-f15 is shown in Scheme 2. A mixture of recrystallised anthranilic acid (0.01 mol), acetic anhydride (0.02 mol), and acetic acid (0.01 mol) was taken in a round-bottomed flask and refluxed for 4 h. The acetic acid together with acetic anhydride was distilled off under reduced pressure.…”

mentioning

confidence: 99%

Synthesis and antimicrobial activity of novel 2-Methyl-3-(1′3′4′-Thiadiazoyl)-4-(3h) Quinazolinones

Jatav¹,

Sk²,

Kashaw³

et al. 2006

Indian J Pharm Sci

View full text Add to dashboard Cite

With a view to explore the versatile lead molecule 4(3H)-quinazolinones, a series of novel 2-methyl-3-(1'3'4' thiadiazoyl)-4-(3H) quinazolinones have been synthesised by reacting 2-amino-5-aryl/alkyl-1'3'4'-thiadiazoyl with 2-substituted benzoxazin-2-one. The designed compounds (5a-f) were screened in vitro for antibacterial activity on Staphylococcus aureus, Bacillus subtilis, and Escherichia coli. Antifungal activity was screened against Candida albicans, Aspergillus niger, and Curvularia lunata. Synthesised compounds exhibited both antibacterial and antifungal activity. Quinazolinone is a versatile lead molecule for designing potential bioactive agents. 4(3H)-Quinazolinone and its derivatives have been reported to exhibit analgesic, anaesthetic, antibacterial, anticancer, anticonvulsant, antimicrobial, antihypertensive, antiinflammatory, diuretic, muscle-relaxant, sedative, diuretic, CNS-depressant, and tranquilizer properties 1-6. We have already reported the biological activities of 1, 3, 4-thiadiazoles, including antimicrobial activities 7-8. This work was undertaken with a view to explore the possibility of antimicrobial activity in the present nucleus, which has both 4(3H)-quinazolinone and 1'3'4'-thiadiazoles in it. Six new 2-methyl-3-(1'3'4'-thiadiazoyl)-4(3H)-quinazolinones were synthesised and evaluated for their antimicrobial and antifungal activity. Anthranilic acid reacts with acetic anhydride and acetic acid to form corresponding 2-methylbenzoxazin-2 one by N-acylation, followed by dehydrative cyclization mechanism 9. The 2-methylbenzoxazin-2-ones condensed with the primary amino groups of 1'3'4'-thiadiazolyl group (aromatic and aliphatic) to form 2-methyl-3-(1'3'4'-thiadiazoyl)-4(3H) quinazolinones. Melting points were determined in open glass capillary and are uncorrected. The purity was checked by TLC using silica gel G as stationary phase and hexane: ethanol: chloroform (1:3:6) as mobile phase. The structure of the synthesised compounds were

show abstract

mentioning

confidence: 99%

Synthesis and antimicrobial activity of novel 2-Methyl-3-(1′3′4′-Thiadiazoyl)-4-(3h) Quinazolinones

Jatav¹,

Sk²,

Kashaw³

et al. 2006

Indian J Pharm Sci

View full text Add to dashboard Cite

show abstract

Oxoquinazolines and 5‐, 6‐, 7‐, and 8‐Hydroxyquinazolines

1967

Chemistry of Heterocyclic Compounds: A Series of Monographs

View full text Add to dashboard Cite

Synthesis of 6,7‐dihydroxy‐2‐methyl‐4‐quinazolone

Gadekar¹,

Kotsen²

1968

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

THE SYNTHESIS OF 2-METHYL-5-NITRO-4-KETODIHYDROQUINAZOLINES FROM 6-NITROACETANTHRANIL AND PRIMARY AMINES.¹

Cited by 11 publications

References 0 publications

Synthesis and antimicrobial activity of novel 2-Methyl-3-(1′3′4′-Thiadiazoyl)-4-(3h) Quinazolinones

Synthesis and antimicrobial activity of novel 2-Methyl-3-(1′3′4′-Thiadiazoyl)-4-(3h) Quinazolinones

Oxoquinazolines and 5‐, 6‐, 7‐, and 8‐Hydroxyquinazolines

Synthesis of 6,7‐dihydroxy‐2‐methyl‐4‐quinazolone

Contact Info

Product

Resources

About

THE SYNTHESIS OF 2-METHYL-5-NITRO-4-KETODIHYDROQUINAZOLINES FROM 6-NITROACETANTHRANIL AND PRIMARY AMINES.1

Cited by 11 publications

References 0 publications

Synthesis and antimicrobial activity of novel 2-Methyl-3-(1′3′4′-Thiadiazoyl)-4-(3h) Quinazolinones

Synthesis and antimicrobial activity of novel 2-Methyl-3-(1′3′4′-Thiadiazoyl)-4-(3h) Quinazolinones

Oxoquinazolines and 5‐, 6‐, 7‐, and 8‐Hydroxyquinazolines

Synthesis of 6,7‐dihydroxy‐2‐methyl‐4‐quinazolone

Contact Info

Product

Resources

About

THE SYNTHESIS OF 2-METHYL-5-NITRO-4-KETODIHYDROQUINAZOLINES FROM 6-NITROACETANTHRANIL AND PRIMARY AMINES.¹