- Green synthesis of 5 arylidene-2,4-thiazolidinedione, 5-benzylidene rhodanine and dihydrothiophene derivatives catalyzed by hydrated ionic liquid tetrabutylammonium hydroxide in aqueous medium
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An efficient synthesis of 5 arylidene-2,4-thiazolidinediones and 5-benzylidene rhodanines by the Knoevenagel condensation of 2,4- thiazolidinedione or rhodanine with aromatic aldehydes was studied. It proceeded smoothly in the presence of tetrabutylammonium hydroxide/H2O-EtOH to afford the corresponding products in high yields at 50C. Also, a series of dihydrothiophene derivatives were synthesized via the four-component reaction of aldehyde, malonitrile, 2,4-thiazolidinedione, and piperidine in the presence of Bu4NOH as a basic ionic liquid in aqueous medium. This new method offers several advantages, such as excellent yields, short reaction times, and simple procedure(Equation presented). 2013
- Khazaei, Ardeshir,Veisi, Hojat,Safaei, Maryam,Ahmadian, Hossein
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p. 270 - 278
(2014/04/03)
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- Facile and convenient synthesis of 5-arylalkylidenerhodanines by electrocatalytic crossed aldol condensation
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An electrochemically induced catalytic crossed Aldol condensation of one equivalent of rhodanine with various aromatic aldehydes and ketones in ethanol in an undivided cell in the presence of sodium bromide as an electrolyte results in the formation of th
- Veisi, Hojat,Vafajoo, Zahra,Maleki, Behrooz,Maghsoodlou, Malek Taher
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p. 672 - 677
(2013/07/26)
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- Urea/thiourea catalyzed, solvent-free synthesis of 5-arylidenethiazolidine- 2,4-diones and 5-arylidene-2-thioxothiazolidin-4-ones
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An efficient and organo-catalyzed method has been developed for the synthesis of 5-arylidenethiazolidine-2,4-diones and 5-arylidene-2- thioxothiazolidin-4-ones via Knoevenagel condensation of arylaldehydes 1 and 2,4-thiazolidinedione 2a/2-thioxothiazolidin-4-one 2b under mild conditions. Urea-adduct 4 and azomethine 5 also afford arylidene-products 3 by reacting with 2a-b via addition-elimination reaction. This protocol has the features of use of inexpensive, ecofriendly readily available, effective catalyst system viz. urea/thiourea, avoidance of volatile solvents, excellent yield and simple work-up procedure.
- Shah, Sakshi,Singh, Baldev
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experimental part
p. 5388 - 5391
(2012/09/22)
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- A solvent-free protocol for the green synthesis of arylalkylidene rhodanines in a task-specific ionic liquid
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2-Hydroxyethylammonium formate acts as a task-specific ionic liquid (TSIL) for the Knoevenagel condensation of carbonyl compounds with rhodanine to afford arylalkylidene rhodanines under solvent-free conditions and in good-to-excellent yields. Additionally, compared with those in organic solvents, the yields obtained in the presence of our ionic liquid (IL) were significantly increased. The detailed mechanism of the catalytic effect of TSIL is also reported for the first time.
- Alizadeh, Abdolhamid,Khodaei, Mohammad M.,Eshghi, Ali
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experimental part
p. 514 - 518
(2010/08/04)
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- Iodine catalysed synthesis of 5-(arylmethylidene)rhodanines by grinding under solvent-free conditions
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5-(Arylmethylidene)rhodanines have been synthesised in 88-95% yields by Knoevenagel condensation of various aromatic aldehydes with rhodanine in the presence of a catalytic amount of iodine at room temperature by grinding under solvent-free conditions.
- Wang, Hongshe,Zeng, June
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experimental part
p. 374 - 376
(2009/12/31)
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- Green synthesis of 5-benzylidene rhodanine derivatives catalyzed by 1-butyl-3-methyl imidazolium hydroxide in water
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A basic functionalized ionic liquid, 1-butyl-3-methyl imidazolium hydroxide ([bmim][OH]), catalyzed the Knoevenagel condensation of rhodanine with aromatic aldehydes. It proceeded smoothly in water to afford the 5-benzylidene rhodamine derivatives in high yields at room temperature. This new method offers several advantages, such as excellent yields, short reaction times, and simple procedure. The catalyst can be reused at least 5 times without significant loss of activity.
- Gong, Kai,He, Zhi-Wei,Xu, Ying,Fang, Dong,Liu, Zu-Liang
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experimental part
p. 913 - 915
(2009/09/06)
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