title: Synthesis of 2-(1,5-diaryl-1,4-pentadien-3-ylidene)-hydrazinecarboximidamide hydrochloride catalyzed by p-dodecylbenzenesulfonic acid in aqueous media under ultrasound irradiation.
abstract: Amidinohydrazone compounds are very important synthetic intermediates and can serve as versatile precursors in synthesis of many natural products and drug molecules. The use of ultrasound, p-dodecylbenzenesulfonic acid (DBSA) and water as solvent improved the synthesis of different 2-(1,5-diaryl-1,4-pentadien-3-ylidene)-hydrazinecarboximidamide hydrochlorides. The best reaction conditions for the condensation of 1,5-diphenyl-1,4-pentadien-3-one with aminoguanidine hydrochloride were as follows: 1,5-diphenyl-1,4-pentadiene-3-one (1, 1 mmol), aminoguanidine hydrochloride (1.1 mmol), DBSA (0.5 mmol), water 10 mL, reaction temperature 25-27°C, irradiation frequency 25 kHz. 2a was achieved in 94% yield within 2h. The other seven amidinohydrazones were obtained in 84-94% yield within 2-3h under the same conditions. Compared to the method involving catalysis by hydrochloric acid in refluxing EtOH, the advantages of present procedure are milder conditions, shorter reaction times, higher yields, and environmental friendly conditions, which make it a useful strategy for the synthesis of analogues.
authors.affiliation: Key Laboratory of Analytical Science and Technology of Hebei Province, Ministry of Education, College of Chemistry and Environmental Science, Hebei University, Baoding, PR China. lijitai@hbu.cn
authors.forename: Ji-Tai
authors.initials: JT
authors.lastname: Li
authors.forename: Chao
authors.initials: C
authors.lastname: Du
authors.forename: Xiao-Ya
authors.initials: XY
authors.lastname: Xu
authors.forename: Guo-Fen
authors.initials: GF
authors.lastname: Chen
mesh_terms: D001557:Benzenesulfonates / Q000737:chemistry*; D002384:Catalysis; D006146:Guanidines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D014465:Ultrasonics; D014867:Water / Q000737:chemistry
chemical_list: D001557:Benzenesulfonates; D006146:Guanidines; D014867:Water; C001114:dodecylbenzenesulfonic acid; C004479:pimagedine