325471-92-9

Upstream product

• 39794-30-4 N-(3,4-dimethoxy-benzylidene)benzhydrazone 
• 613-94-5 benzoic acid hydrazide 
• 120-14-9 3,4-dimethoxy-benzaldehyde 

Relevant academic research and scientific papers

IBX/KI promoted synthesis of 2, 5-disubstituted 1, 3, 4-oxadiazoles

Background: Oxadiazoles are privileged scaffolds in different areas of medicinal, pesticidal, polymer and material science. They act as anticancer, benzodiazepine receptor agonists, antimicrobial, analgesic, diuretic and tyrosinase inhibitors etc. A number of compounds containing an oxadiazole moiety are in late stage clinical trials including zibotentan and furamizole. Despite numerous methods are reported, the majority of them suffer from major drawbacks such as the use of strong alkaline or acidic conditions, highly toxic and corrosive reagents and also involve the use of costly reagents, elevated temperatures and longer reaction times. Inspired by the potential application of hypervalent iodonium reagents in organic synthesis, we would like to explore the readily available IBX and KI reagents for the facile synthesis of 1, 3, 4-oxadiazoles. Method: Oxidative cyclization has successfully been developed for the synthesis of 2, 5-disubstituted 1, 3, 4-oxadiazoles. Results: An efficient process for the one-pot synthesis of 2, 5-disubstituted 1, 3, 4-oxadiazoles has been developed using IBX/KI system at 25°C. The reaction was successful with a wide range of substrates such as aromatic and heterocyclic aldehyde and arylhydrazides to afford the corresponding unsymmetrical 2, 5-disubstituted 1, 3, 4-oxadiazoles. The mild reaction conditions, cost-effective reagents and short reaction time are noteworthy advantages of this methodology. Conclusion: We have developed a one-pot strategy for the synthesis of 1, 3, 4-oxadiazioles using a combination of IBX/KI at ambient temperature. This one-pot procedure proved to be quite general and worked well with a wide variety of aryl and heterocyclic aldehydes and variety of acylhydrazides. The advantage of this method lies in the simplicity of experimental procedure and the ready accessibility of the reagents, which render this, an experimentally attractive method for the preparation of unsymmetrical 1, 3, 4-oxadiazoles.

2,4,6-Tris[(4-dichloroiodo)phenoxy)]-1,3,5-triazine as a new recyclable hypervalent iodine(III) reagent for chlorination and oxidation reactions

The synthesis of 2,4,6-tris[(4-dichloroiodo)phenoxy)]-1,3,5-triazine, as a new recyclable nonpolymeric analogue of (dichloroiodo)benzene, is achieved in two steps using 2,4,6-trichloro-1,3,5-triazine and 4-iodophenol. The application of 2,4,6-tris[(4-dichloroiodo)phenoxy)]-1,3,5-triazine for the chlorination reaction of various activated arenes, olefin, and 1,3-diketone is demonstrated. The reagent 2,4,6-tris[(4-dichloroiodo)phenoxy)]-1,3,5-triazine can be applied also for the oxidative synthesis of 1,3,4-oxadiazoles and 1,2,4-thiadiazoles under mild conditions in excellent yields. The recyclability of the 2,4,6-tris[(4-dichloroiodo)phenoxy)]-1,3,5-triazine was possible owing to the facile recovery and reuse of the coproduced 2,4,6-tris(4-iodophenoxy)-1,3,5- triazine from the reaction mixture due to its practical insolubility in methanol. Georg Thieme Verlag Stuttgart, New York.

Cu(II) catalyzed imine C-H functionalization leading to synthesis of 2,5-substituted 1,3,4-oxadiazoles

A direct access to symmetrical and unsymmetrical 2,5-disubstituted [1,3,4]-oxadiazoles has been accomplished through an imine C-H functionalization of N-arylidenearoylhydrazide using a catalytic quantity of Cu(OTf)2. This is the first example of amidic oxygen functioning as a nucleophile in a Cu-catalyzed oxidative coupling of an imine C-H bond. These reactions can be performed in air atmosphere and moisture making it exceptionally practical for application in organic synthesis.