62407-65-2Relevant academic research and scientific papers
Anomalous Direction of the Ene Reaction of Pulegone with 4-Phenyl-3H-1,2,4-triazole-3,5(4H)-dione
Bodrikov,Kurskii, Yu. A.,Chiyanov,Subbotin, A. Yu.,Kozlov,Korovnikova, Yu. S.
, p. 1430 - 1431 (2018)
The ene reaction of pulegone with 4-phenyl-3H-1,2,4-triazole-3,5(4H)-dione, apart from the two previously described products, epimeric 1-[(1S,4R)- and 1-[(1R,4R)-4-methyl-2-oxo-1-(prop-1-en-2-yl)cyclohexyl]-4-phenyl-1,2,4-triazolidine-3,5-diones, gave one more isomer, 1-{1-methyl-1-[(4R)-4-methyl-6-oxocyclohex-1-en-1-yl]ethyl}-4-phenyl-1,2,4-triazolidine-3,5-dione. The latter is formed as a result of addition of 4-phenyl-3H-1,2,4-triazole-3,5(4H)-dione to the Me2C= carbon atom of pulegone (anti-Markovnikov addition) and double bond migration to the six-membered carbocycle.
Ene-type adducts from the reaction of 4-phenyl-1,2,4-triazoline-3,5-dione with β-alkyl s-cis enones
Hunter, Norman Robert,Krawchuk, Bert Paul,Shiloff, Janice Deborah
, p. 835 - 839 (2007/10/02)
The adducts from the reaction of 4-phenyl-1,2,4-triazoline-3,5-dione with a number of α,β-unsaturated ketones have been isolated and characterized.The reaction generally proceeds with migration of the double bond to the β,γ-position and is highly chemoselective towards reaction with enones which have , or can assume, an s-cis conformation.
Regio- and Stereoselectivity in the Ene Reaction of N-Phenyl-1,2,4-triazoline-3,5-dione with α,β-Unsaturated Carbonyl Substrates
Hoye, Thomas R.,Bottorff, Kyle J.,Caruso, Andrew J.,Dellaria, Joseph F.
, p. 4287 - 4292 (2007/10/02)
N-Phenyltriazoline-3,5-dione reacts with α,β-unsaturated ketones,esters, and lactones 1a-l to give ene adducts 2a-l.The reactions usually proceed in good yield with high regioselectivity and, where possible, high stereoselectivity.Ene substrates capable of adopting an s-cis conformation show much greater reactivity.A variety of mechanistic interpretations is considered.
