684282-69-7Relevant academic research and scientific papers
The structure of side product in the synthesis of substituted 1,3-tropolones
Tkachev,Aldoshin,Shilov,Sayapin,Komissarov,Minkin
, p. 275 - 277 (2006)
The structure of pyrocatechol p-toluenesulfonate resulting from the reaction between 3,5-di(tertbutyl)-1,2-benzoquinone and substituted 2-methylquinolines was proved by X-ray diffraction analysis. Pleiades Publishing, Inc. 2006.
New method for the synthesis of β-tropolones: Structures of condensation products of o-quinones with 2-methylquinolines and the mechanism of their formation
Minkin,Aldoshin,Komissarov,Dorogan,Sayapin,Tkachev,Starikov
, p. 2032 - 2055 (2006)
A new method was developed for the synthesis of functionalized β-tropolones based on acid-catalyzed condensation of 2-methylquinoline derivatives with 3,5-di(tert-butyl)-1,2-benzoquinone and 4,6-di(tert-butyl)-3- nitro-1,2-benzoquinone (14). The mechanism of the multistep reaction giving rise to β-tropolones and their tautomerism were studied by quantum chemical methods (DFT B3LYP/6-31G**). The reaction of 2-methylquinoline derivatives containing the tertiary amino group at position 4 with quinone 14 is accompanied by the formation of derivatives of a new heterocyclic system, viz., 4,6-dioxo-2-azabicyclo[3.3.0]octa-2,7-diene N-oxide. The molecular and crystal structures of two 5,7-di(tert-butyl)-3-hydroxy-2-(quinolin-2-yl)tropolones and two dioxoazabicyclooctadiene N-oxides, as well as of the preparatively isolated intermediate of the first condensation step and of the by-product of the reaction were established by X-ray diffraction.
