936132-85-3Relevant academic research and scientific papers
Iodine-catalyzed diazenylation with arylhydrazine hydrochlorides in air
Barak, Dinesh S.,Dighe, Shashikant U.,Avasthi, Ilesha,Batra, Sanjay
, p. 3537 - 3546 (2018/04/14)
A mild approach to diazenylation of active methylene compounds and N-heterocyclic compounds with arylhydrazine hydrochlorides in the presence of iodine under basic aerobic conditions was developed. The reaction could be executed either under heating or in the presence of blue LED light, though the latter condition was found to be relatively efficient. Presumably, the aryldiazene produced by oxidation of arylhydrazine hydrochloride acts as a nitrogen scavenger of the radical intermediate generated from the active methylene compound in the presence of iodine to produce the diazo compounds. The scope and limitations of the protocol are presented.
Improved protocol for Thorpe reaction: Synthesis of 4-amino-1-arylpyrazole using solid-liquid phase-transfer conditions
Desai, Nirmal D.,Shah, Rina D.
, p. 316 - 327 (2008/09/16)
Solid-liquid phase-transfer conditions were employed for the first time in the Thorpe reaction to synthesize 4-amino-1-aryl-3,5-substituted-1H-pyrazoles 3. Aryl amines were diazotized and coupled with various active methylene compounds such as cyano aceta
Studies with 3-functionally substituted 2-arylhydrazononitriles: A new route to 3-substituted-2-arylhydrazononitriles, 4-amino-pyrazole-5- carbonitriles, azadienes and cinnolines
Abdel-Motaleb, Ramadan M.,Makhloof, Abdel-Moneim A.,Ibrahim, Hamada M.,Elnagdi, Mohamed H.
, p. 931 - 934 (2007/10/03)
3-Amino-3-phenyl-2-phenylazoacrylonitrile 6 is obtained in good yield via reaction of 5 with phenyl magnesium bromide. The compound 6 is readily converted into 4a. The so formed alkanenitrile reacted with phenylmagnesium bromide to yield 8. Compound 8 cou
A microwave assisted diazo coupling reaction: The synthesis of alkylazines and thienopyridazines
Al-Mousawi, Saleh,Elassar, Abdel-Zaher,El-Apasery, Morsy
, p. 1755 - 1771 (2007/10/03)
Heating diazoaminobenzene with active methylene compounds 1-3 in microwave oven in acetic acid, in the presence of hydrochloric acid, afforded the corresponding arylhydrazones 5-7. These reaction products were condensed with ethyl cyanoacetate in a domestic microwave oven after 1-2 minutes heating to yield the pyridazinones 8-12. Compounds 8c and 12 reacted with sulfur in basic DMF solution, in microwave oven using MORE technology to yield the thienopyridazinone 14 and 16 respectively. While 17 was produced when 8b was treated like wise with sulfur and DMF in the presence of piperidine. Compounds 16 coupled with aromatic diazonium salts to yield arylazo derivatives 21a-c. Copyright Taylor & Francis Group, LLC.
Chemistry of 2-arylhydrazonals: Utility of substituted 2-arylhydrazono-3- oxoalkanals as precursors for 3-oxoalkanonitriles, 3-aminoisoxazole and 1,2,3- and 1,2,4-triazoles
El-Dusouqui, Osman M. E.,Abdelkhalik, Mervat M.,Al-Awadi, Nouria A.,Dib, Hicham H.,George, Boby J.,Elnagdi, Mohammed H.
, p. 295 - 302 (2007/10/03)
Efficient routes to 2-arylhydrazono-3-oxoalkanonitriles, 1,2,3- and 1,2,4-triazoles, and 3-aminoisoxazole utilising the oximes of the title hydrazones are reported. The behaviour of the oximes on pyrolysis in the gas phase and by flash vacuum is analysed.
Studies with 3-substituted 2-arylhydrazono-3-oxoaldehydes: New routes for synthesis of 2-arylhydrazono-3-oxonitriles, 4-unsubstituted 3,5-diacylpyrazoles and 4-arylazophenols
Al-Saleh, Balkis,El-Apasery, Morsy A.,Elnagdi, Mohamed Hilmy
, p. 578 - 580 (2007/10/03)
Compounds 1a-c reacts with hydroxylamine-O-sulfonic acid or with hydroxylamine hydrochloride in aqueous acetic acid in the presence of sodium acetate to yield the 3-oxoalkanonitriles 3, which were converted into arylazoisoxazole and 1,2,4-triazine derivatives 10. The hydrazones 1a-c reacted with chloroacetone or with phenacyl bromide in refluxing ethanol and in presence of K2CO3 to yield the pyrazoles 12a-e, formed most likely via intermediately formed 11a-e. The reaction of 1a,b with acetone afforded the arylazophenols.
Studies with 2-Arylhydrazono-3-oxopropanals: A novel route to 4-aroyl-2-aryl-1,2,3-triazoles, 3-substituted 4-arylazopyrazoles, 2-substituted glyoxalonitrile and 3-oxoalkanonitriles
Abdel-Khalik, Mervat Mohammed,Agamy, Samia Michel,Elnagdi, Mohammed Hilmy
, p. 1211 - 1215 (2007/10/03)
2-Arylhydrazono-3-oxopropanals 1 react with hydroxylamine hydrochloride to yield the corresponding oximes 3 that are cyclized into isoxazoles 9 on reflux in acetic anhydride and are converted into 2-arylhydrazono-3-oxonitriles (4) on treatment with pyridine. The reaction of 1 with hydrazines afforded dihydrazones 10 which were converted to arylazopyrazoles 11 when treated with pyridine, whereas treatment with an acidic reagent resulted in the formation of 3-aroyl-2-phenyl-1,2,3-triazoles 12.
