Synthesis and Characterizations of New 1, 3-Oxazine Derivatives (original) (raw)
Related papers
European Journal of …, 2012
A series of new 1,3-disubstituted-1H-naphtho[1,2-e][1,3]oxazines (3 and 7) was synthesized in good yields and the structure was determined with the help of NMR, 2D-NMR, HRMS studies and X-ray crystallography. These compounds were tested in vitro for their antibacterial activity against Grampositive and Gram-negative bacteria and as well as for antifungal activity. The compounds 3c, 3e, 7a, 7d and 7k showed significant antibacterial activity and 7l showed moderate antifungal activity. The cytotoxicity of 1,3-disubstituted-1H-naphtho[1,2-e][1,3]oxazines showed that 3e and 7e are more effective against breast, lung and colon cell proliferation.
Synthesis, antimicrobial and cytotoxicity study of 1,3-disubstituted-1H-naphtho[1,2-e][1,3]oxazines
European Journal of Medicinal Chemistry, 2012
A series of new 1,3-disubstituted-1H-naphtho[1,2-e][1,3]oxazines (3 and 7) was synthesized in good yields and the structure was determined with the help of NMR, 2D-NMR, HRMS studies and X-ray crystallography. These compounds were tested in vitro for their antibacterial activity against Grampositive and Gram-negative bacteria and as well as for antifungal activity. The compounds 3c, 3e, 7a, 7d and 7k showed significant antibacterial activity and 7l showed moderate antifungal activity. The cytotoxicity of 1,3-disubstituted-1H-naphtho[1,2-e][1,3]oxazines showed that 3e and 7e are more effective against breast, lung and colon cell proliferation.
Synthesis and Characterization of New 3,4-Dihydro-2H-benzo- and Naphtho-1,3-oxazine Derivatives
Asian Journal of Chemistry, 2016
The synthesis of benzoxazine compounds dates back over 70 years [1-4] but their potential was only realized recently [5]. Among all benzoxazine compounds, 1,3-benzoxazine have received greater attention as they are used in the production of polymeric materials [6-8] and are also of significant interest in pharmacological fields [9]. 1,3-Benzoxazines as monomers are used in the synthesis of a new type of phenolic resins called polybenzoxazines through thermally activated ring-opening polymerization [10,11]. These polybenzoxazines possesses not only the properties of traditional phenolic resins but other unique properties such as low water absorption, high modulus, high strength, high glass transition temperatures, high char yield and low volumetric shrinkage upon curing [12-15]. Furthermore, 1,3-benzoxazines are known for their wide range of biological activities and hence used as fungicides, bactericide, anti-inflammatory, antidepressants and antitumor agents [16,17]. Numerous approaches are used for the synthesis of 1,3benzoxazine compounds using different solvents [18-20]. Among the approaches is the step-wise procedure which has recently gained considerable interest and more importantly tolerates various functional groups [21]. For this reason, the
An Efficient and Solvent Free Synthesis of N-Aryl 2,3-Dihydro-4H naphtho-[2,1-e] 1,3-oxazines
Biomedical Journal of Scientific & Technical Research, 2020
Oxazine compounds have proved to have many pharmaceutical applications and most of these compounds now a days are used as drugs. For the importance of this class of heterocyclic compounds we are here investigate the synthesis of new derivatives of 1,3-oxazines using solvent free one pot three component system in a drug discovery program ,so starting from β-Naphthol, formaldehyde and aromatic amines in presence of zarconyl chloride as catalyst. compounds 1-9 were synthesized, Benzo 1,3 diazines (10-14) were also synthesized from their corresponding 1,3 oxazines. These compounds were characterized by IR, some representative by [1] HNMR and were discussed.
European Journal of Medicinal Chemistry, 2010
A series of 3,4-dihydro-2H-benzo[e]-, 2,3-dihydro-1H-naphtho[1,2-e]-, 3,4-dihydro-2H-naphtho[2,1e][1,3]oxazine and 1,2-bis(3,4-dihydrobenzo[e][1,3]oxazin-3(4H)-yl)ethane derivatives was obtained through an eco-friendly Mannich type condensation-cyclization reaction of phenols or naphthols with formaldehyde and primary amines in water at ambient temperature. Preliminary in vitro antimicrobial activity of the synthesized compounds was assessed against six pathogenic fungi, two Gram-negative and two Gram-positive bacteria. Some of the screened compounds have shown significant in vitro antimicrobial effect. Cytotoxic activities of the lead compounds (2m, 2n, 3c and 3d) against mouse fibroblast cell line (L929) were determined by MTT method. The assay results revealed that these molecules offered remarkable viability (>90%) of L929 cells at concentration of 25 mg/mL.
Synthesis and conformational analysis of new naphth[1,2-e][1,3]oxazino[3,4-c]quinazoline derivatives
Tetrahedron, 2011
Synthesis and conformational analysis of new naphth[1,2-e][1,3]oxazino[3,4-c] quinazoline derivatives Ren ata Cs € ut € ort € oki a , Istv a b s t r a c t A new highly functionalized aminonaphthol derivative, 1-(amino(2-aminophenyl)methyl)-2-naphthol (4), was synthesized by the reaction of 2-naphthol, 2-nitrobenzaldehyde and tert-butyl carbamate or benzyl carbamate, followed by reduction and/or removal of the protecting group. The aminonaphthol derivative thus obtained was converted in ring-closure reactions with formaldehyde, benzaldehyde and/ or phosgene to the corresponding naphth[1,2-e][1,3]oxazino[3,4-c]quinazoline derivatives. The conformational analysis of some derivatives by NMR spectroscopy and accompanying molecular modelling are also reported.
Journal of Combinatorial Chemistry, 2010
A series of new naphtho[1,2-e][1,3]oxazine derivatives such as trans-1,3-diaryl-1H-naphtho[1,2-e][1,3]oxazine-2(3H)-carbonyl chloride, 1-aryl-2-benzyl-1,2-dihydronaphtho[1,2-e][1,3]oxazine-3-one, and trans-1,3-diaryl-1H-naphtho[1,2-e] [1,3]oxazine-2(3H)-carbaldehyde were selectively synthesized via a chemoselective reaction of 1,3-diaryl-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazines and triphosgene or triethyl orthoformate, respectively, induced by different low-valent titanium systems. This method has the advantages of short reaction time (15 min), convenient manipulation, and high chemoselectivity.
Synthesis and study biological activity of some 1,8- Naphthyriane Derivatives
Al-Kufa University Journal for Biology
The compound 4-carboxy -2-phenyl-1,8- naphthyridine was synthesized from pyruvic acid, 2-Aminopyridine and Benzaldchyde (I).4-Hydrocynoamine-2-phenyl-1,8- Naphthyridine synthhesized from 4-Carboxy-2-phenyl-1.8-naphthyridine and phosphor penta chloride anhydrous in carbon tetra chloride, the resultant derivative was then separated by crushed ice and filtrated, the solid acid chloride thus obtained was used for further reaction. to the solid which was form was added hydrazine hydrate (II).4(p-phenyl dimethyl aminc) -hydrazine)-1,8-Naphthyridine (III) was synthesized from refluxed equimolar quantities of (II) with p.Dimethylamino- Benzaldephyde in ethanol. The purity of the synthesized compounds were established through R spectroscopy. and the purity were confirmed by TLC. the physical properties such as melting point and percentage were determined. The antibacterial activity of synthesized compounds (I, II, III) were tested by using agar diffusion method against some bacterial species...
Synthesis and conformational analysis of naphthylnaphthoxazine derivatives
Journal of Molecular Structure, 2009
Through the cyclization of 1-(b-hydroxynaphthyl)-1,2,3,4-tetrahydroisoquinoline and 1-(a-hydroxynaphthyl)-1,2,3,4-tetrahydroisoquinoline with formaldehyde, phosgene, p-nitrobenzaldehyde or p-chlorophenyl isothiocyanate, 8-substituted 10,11-dihydro-8H,15bH-naphth[1,2-e][1,3]oxazino[4,3-a]isoquinolines (3 and 4) and 10,11-dihydro-8H,15bH-naphth[2,1-e][1,3]oxazino[4,3-a]isoquinolines (15 and 16) were prepared. Conformational analysis of both the piperidine and the 1,3-oxazine moieties of these heterocycles by NMR spectroscopy and an accompanying theoretical study revealed that these two conformationally flexible six-membered ring moieties prefer twisted chair conformers.