Topic
Acetylacetone
About: Acetylacetone is a research topic. Over the lifetime, 4244 publications have been published within this topic receiving 56558 citations. The topic is also known as: Hacac & acetyl 2-propanone.
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TL;DR: Two distinct reaction pathways are explored toward the formation of the Michael product that differ in the mode of electrophile activation, and both reaction channels are shown to be consistent with the notion of noncovalent organocatalysis in that the transition states leading to the Michael adduct are stabilized by extensive H-bonded networks.
Abstract: The mechanism of enantioselective Michael addition of acetylacetone to a nitroolefin catalyzed by a thiourea-based chiral bifunctional organocatalyst is investigated using density functional theory calculations. A systematic conformational analysis is presented for the catalyst, and it is shown that both substrates coordinate preferentially via bidentate hydrogen bonds. The deprotonation of the enol form of acetylacetone by the amine of the catalyst is found to occur easily, leading to an ion pair characterized by multiple H-bonds involving the thiourea unit as well. Two distinct reaction pathways are explored toward the formation of the Michael product that differ in the mode of electrophile activation. Both reaction channels are shown to be consistent with the notion of noncovalent organocatalysis in that the transition states leading to the Michael adduct are stabilized by extensive H-bonded networks. The comparison of the obtained energetics for the two pathways allows us to propose an alternative mec...
367 citations
349 citations
TL;DR: In this paper, 3-(2-methylbenzimidazol-1-yl)propanoic acid hydrazide (1) with CS2/KOH gave oxadiazole 2 which underwent Mannich reaction to give triazole 4 which was treated with both aldehydes and acetic anhydride to give 5 and 6, respectively.
Abstract: Reaction of 3-(2-methylbenzimidazol-1-yl)propanoic acid hydrazide (1) with CS2/KOH gave oxadiazole 2 which underwent Mannich reaction to give 3. Compound 2 was treated with hydrazine hydrate to give triazole 4 which was treated with both aldehydes and acetic anhydride to give 5 and 6, respectively. Carbohydrazide 1 was reacted with ethyl acetoacetate, acetylacetone and aldehydes to give 7, 8 and 9, respectively. Cyclocondensation of 9 with thioglycolic and thiolactic acids gave 10 and 11, respectively. Some of these compounds showed potential antimicrobial activities.
316 citations
TL;DR: Curcumin has been prepared in 80% yield from vanillin and acetylacetone/B2O3 in the presence of tri-sec. butyl borate and butylamine.
Abstract: Curcumin has been prepared in 80% yield from vanillin and acetylacetone/B2O3 in the presence of tri-sec. butyl borate and butylamine. The reaction was carried out in ethyl acetate at room temperature. Eight compounds related to curcumin have also been synthesized.
301 citations
TL;DR: Titania nanotubes with high photo-catalytic activity were synthesized in laurylamine hydrochloride / tetraisopropyl orthotitanate modified with acetylacetone system as mentioned in this paper.
Abstract: Titania nanotubes with high photo-catalytic activity were synthesized in laurylamine hydrochloride / tetraisopropyl orthotitanate modified with acetylacetone system. Formation of nanotubes was confirmed by transmission electron microscope images. These titania nanotubes had crystal structure of anatase and showed high photo-catalytic activity, i.e., the activity is about three times higher than Degussa-P-25 and higher than ST-01.
294 citations