- The preparation of intercalating isoxazoles via a nitrile oxide cycloaddition
-
Pyridinium chlorochromate oxidation of 9-methylacridine (2) affords the corresponding aldehyde 3 in good yield. Conversion of the aldehyde to the hydroximinoyl chloride 5a was accomplished via reaction of the corresponding oxime with N-chlorosuccinimide. Dipolar addition to the enamine of ethylacetoacetate provided the corresponding isoxazoles 1 in good yield.
- Mosher,Natale
-
-
Read Online
- Design and synthesis of sinomenine isoxazole derivatives via 1,3-dipolar cycloaddition reaction
-
A novel structure of sinomenine isoxazole derivatives is synthesised from sinomenine hydrochloride and aromatic aldehydes and requires six steps. 19 target compounds have been obtained in good yields. The sinomenine hydrochloride transforms to 4-alkynyl sinomenine, which is a key intermediate product to synthesise the target sinomenine isoxazole compounds, after a neutralisation reaction with ammonia and substitution reaction with 3-chloropropyne. Another key intermediate product is 1,3-dipole, which can be obtained from aromatic aldehyde. After treatment with hydroxylamine hydrochloride and then sodium carbonate solution, aromatic aldehyde is converted to aldehyde oxime, which reacts with N-chlorosuccinimide (NCS) to afford aryl hydroximino chloride. 1,3-Dipole is eventually formed in situ while triethylamine (TEA) in DMF is added dropwise. Then 4-alkynyl sinomenine is added to provide the sinomenine isoxazole derivative via 1,3-dipolar cycloaddition reaction as the key step. All the target compounds are characterised by melting point, 1H NMR, 13C NMR, HRMS and FT-IR spectroscopy.
- Pan, Hongmei,Lu, Tong,Wu, Xuedan,Gu, Chengwen,Tao, Naili,Zhang, Biao,Wang, Ao,Chen, Guangmei,Zhang, Kehua,Cheng, Jie,Jin, Jie
-
p. 2360 - 2364
(2019/11/11)
-
- Highly regioselective 1,3-dipolar cycloaddition of 3′-O-propargyl guanosine with nitrile oxide: An efficient method for the synthesis of guanosine containing isoxazole moiety
-
The 1,3-dipolar cycloaddition reaction of 3′-O-propargyl guanosine with various in-situ generated nitrile oxides in the presence of DMF as a solvent is described. It is noteworthy that the reaction is highly regioselective that affords biologically import
- Kore, Anilkumar R.,Senthilvelan, Annamalai,Shanmugasundaram, Muthian
-
-
- Biologically active hydroxymoyl chlorides as antifungal agents
-
Several oximes and oxime ethers have been developed as antimicrobial agents. A series of chlorooximes (hydroximoyl chlorides) have been synthesized and tested for antifungal activity under in-vitro conditions against Candida albicans, Candida parapsilosis, Candida glabrata, Candida krusei, Aspergillus fumigatus, Aspergilhis flaviis and Aspergillus niger. The derived antifungal activity has been compared with the corresponding oximes. The results show that most of the chlorooximes exhibit potent antifungal activity with anti-isomers showing better activity. It is observed that most of the chlorooximes show interesting antifungal activity (MICs ≤ 32 μg/mL) compared to oximes. Compound 3q (2,3-dimethoxy phenyl hydroxymoyl chloride) is the most active compound. This compound is active against all the Candida species (MIC 0.5 μg/mL) as well as filamentous fungi with MIC range of 2-4 μg/mL. This series of compounds are fungicidal in nature as evident from the MFC results.
- Ismail, Tabasum,Shafi, Syed,Singh, Parvinder Pal,Qazi, Naveed Ahmed,Sawant, Sanghapal D.,Ali, Intzar,Khan, Inshad Ali,Kumar,Qazi, Ghulam Nabi,Alam, M. Sarwar
-
p. 740 - 747
(2008/12/20)
-
- (Z)-Stereospecific addition of glycosylmercaptans on nitrilium betaines. Synthesis of 1-S-glucopyranosyl arylthiohydroximates
-
With a view to selecting new internal standards for HPLC analysis of glucosinolates, the synthesis of artificial desulfoglucosinolates 5 was carried out.
- Brochard,Joseph,Viaud,Rollin
-
p. 1403 - 1414
(2007/10/02)
-
