77420-62-3Relevant academic research and scientific papers
IBX/KI promoted synthesis of 2, 5-disubstituted 1, 3, 4-oxadiazoles
Khan, P. Rasvan,Durgaprasad,Reddy, S. Gopal,Reddy, G. Raveendra,Hussein, Ibnelwaleed A.,Reddy, B.V. Subba
, p. 64 - 69 (2018/03/05)
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.
Efficient oxidative cyclization of N -acylhydrazones for the synthesis of 2,5-disubstituted 1,3,4-oxadiazoles using t-BuOI under neutral conditions
Gao, Peng,Wei, Yunyang
, p. 113 - 119 (2013/05/23)
An efficient procedure for the oxidative cyclization of N -acylhydrazones was developed utilizing tert-butyl hypoiodite (t-BuOI), which is generated in situ from t -BuOCl and NaI. A variety of 2,5-disubstituted 1,3,4-oxadiazoles were synthesized in high yields within short reaction time. The method is also suitable for cyclization of N -acylhydrazones derived from heterocyclic aldehydes and aliphatic aldehydes. Mild reaction conditions and simple workup operations make the procedure a good alternative for the synthesis of 2,5-disubstituted 1,3,4-oxadiazoles.
Lewis acid-mediated nucleophilic addition of dialkylphosphite to C=N double bond of hydrazones
Lien, Chia-Ling,Yeh, Shu-Hua,Hsu, Chi-Tung
experimental part, p. 543 - 549 (2009/11/30)
The synthesis of new phenyl substituted derivatives (2) of -hydrazino-alkylphosphonic acids by Lewis acid-mediated addition of dialkylphosphite to hydrazones, derived from benzoylhydrazines and benzaldehydes, is described. Reactions were successfully prom
Unsaturated Compounds containing Nitrogen. Part 4. Further Reactions of 1-Chloro-2,3-diazabutadienes with S-Nucleophiles
Flowers, William T.,Robinson, John F.,Taylor, David R.,Tipping, Anthony E.
, p. 349 - 355 (2007/10/02)
1-Chloro-1,4-diaryl-2,3-diazabutadienes (Ar1CCl=NN=CHAr2), prepared by the reaction of thionyl chloride with aroylhydrazones (Ar1CONHN=CHAr2), react with thiosemicarbazide or thiocarbohydrazide to give 2-arylidenehydrazino-5-aryl-1,3,4-thiadiazoles, and with potassium thiocyanate to give 1-thiocyanato-1,4-diaryl-2,3-diazabutadienes which isomerize thermally to arylideneamino-5-aryl-1,3,4-thiadiazoles. 1-Chloro-1,4-diphenyl-2,3-diazabutadiene reacts with potassium ethylxanthate to give a 1-ethylxanthyl-2,3-diazabutadiene which on pyrolysis yields 2,5-diphenyl-1,3,4-thiadiazole.
