Synthesis of 2-(1,5-diaryl-1,4-pentadien-3-ylidene)-hydrazinecarboximidamide hydrochloride catalyzed by p-dodecylbenzenesulfonic acid in aqueous media under ultrasound irradiationUltrasonics Sonochemistry

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Authors
Ji-Tai Li, Chao Du, Xiao-Ya Xu, Guo-Fen Chen
Year
2012
DOI
10.1016/j.ultsonch.2012.02.009
Subject
Radiology Nuclear Medicine and imaging / Chemical Engineering (miscellaneous) / Acoustics and Ultrasonics

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Accepted 24 February 2012

Available online 3 March 2012 oun 2-(1,5-diaryl-1,4-pentadien-3-ylidene)-hydrazinecarboximidamide hydrochlorides. The best reaction catalyzed by hydrochloric acid (classical method) [6]. The method suffers from drawbacks such as a longer reaction time (4–16 h), lower yields, and the use of organic solvent. Therefore, the development of simple, efficient and green methodology for the preparation of amidinohydrazone is still desirable. in many organic reactions [14].

Ultrasound irradiation has been considered as a clean and useful protocol and widely used in organic synthesis in the recent two decades. The most important effect of ultrasound passing through a liquid medium is the generation of cavities. This leads to the development of high temperatures and high pressures within the cavities during their collapse [15]. A large number of organic reactions can be carried out in higher yields, shorter reaction times and milder conditions under ultrasound irradiation [15,16]. Ultrasound has been previously used for the acceleration of condensation, such ⇑ Corresponding authors. Address: College of Chemistry and Environmental

Science, Hebei University, Wusi East Road No. 180, Baoding 071002, PR China. Tel.: +86 312 5079361; fax: +86 312 5079628.

Ultrasonics Sonochemistry 19 (2012) 1033–1038

Contents lists available at

Ultrasonics So elsE-mail address: lijitai@hbu.cn (J.-T. Li).Amidinohydrazone compounds are very important synthetic intermediates and can serve as versatile precursors in synthesis of many natural products and drug molecules [1–5]. These compounds are useful as insecticidal agents [6,7], and anti-tubercular and anti-malarial agents in warm-blooded animals [8,9].

In general, amidinohydrazones are synthesized via the condensation of 1,5-diaryl-1,4-pentadien-3-one with aminoguanidine hydrochloride, with water as a by product. The reaction involves nucleophilic addition of aminoguanidine to the carbonyl, followed by elimination of water. Acid catalysis can aid the reaction [10].

Tomcufcik et al. reported that the synthesis of the title compound was carried out in 40–70% yield under refluxing EtOH via the condensation of bischalcone with aminoguanidine hydrochloride standing of biochemical processes. Water is an inexpensive, abundant, non-toxic, and environmentally friendly solvent. It exhibits unique reactivity and selectivity, which is different from those in conventional organic solvents [11]. In this respect, the development of water-tolerant catalysts has rapidly become an area of intense research [12]. Also, most organic reactants including catalysts are insoluble in water, and the surfactants, due to their hydrophobic and hydrophilic nature, form micelles and promote the reaction in water. p-Dodecylbenzenesulfonic acid (DBSA) as a

Brønsted acid-surfactant combined catalyst acts both as an acid catalyst to activate a substrate and as a surfactant to form stable colloidal dispersion with water-insoluble substrates, and thus can facilitate the reaction [13]. DBSA has been successfully usedKeywords: 1,5-Diaryl-1,4-pentadien-3-one amidinohydrazone hydrochloride

Synthesis

Ultrasound irradiation

Condensation

Aqueous media 1. Introduction1350-4177/$ - see front matter  2012 Elsevier B.V. A doi:10.1016/j.ultsonch.2012.02.009conditions 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 2 h. The other seven amidinohydrazones were obtained in 84–94% yield within 2–3 h 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.  2012 Elsevier B.V. All rights reserved.

Organic reactions in aqueous media have currently attracted increasing interest because of environmental issues and the under-Received 31 August 2011

Received in revised form 8 February 2012 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 differentSynthesis of 2-(1,5-diaryl-1,4-pentadienhydrochloride catalyzed by p-dodecylben under ultrasound irradiation

Ji-Tai Li ⇑, Chao Du, Xiao-Ya Xu, Guo-Fen Chen ⇑

Key Laboratory of Analytical Science and Technology of Hebei Province, Key Laboratory

College of Chemistry and Environmental Science, Hebei University, Baoding 071002, PR a r t i c l e i n f o

Article history: a b s t r a c t

Amidinohydrazone comp journal homepage: www.ll rights reserved.ylidene)-hydrazinecarboximidamide nesulfonic acid in aqueous media edical Chemistry and Molecular Diagnosis, Ministry of Education, a ds are very important synthetic intermediates and can serve as

SciVerse ScienceDirect nochemistry evier .com/ locate /ul tsonch (3  10 mL), the combined organic layer was dried over anhydrous

Na2SO4 and filtered. The solvent was removed by evaporation unH2O

DB -3-y chemas the condensation of carbonyl compounds and hydroxylamine hydrochloride [17], the Knoevenagel condensation of malononitrile with aromatic aldehydes to form arylmethylenemalononitriles [18], the condensation of aromatic aldehydes and barbituric acid [19] and Claisen–Schmidt condensation of acetophenone with aromatic aldehydes [20]. These reactions all involve nucleophilic addition followed by elimination of water. Recently, our laboratory has described the preparation of bis(indolyl)methanes [14b] and 12-aryl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one derivatives catalyzed by DBSA in aqueous media under ultrasound irradiation [21]. To the best of our knowledge, however, there are no reports on the synthesis of the title compound catalyzed by DBSA under ultrasound irradiation. The aims of this study are to improve the syntheses of amidinohydrazone by the use of ultrasonic irradiation (u.s.) and DBSA (Scheme 1). 2. Experimental 2.1. Apparatus, materials and measurements