New method for the synthesis of β-tropolones: Structures of condensation products of o-quinones with 2-methylquinolines and the mechanism of their ... View Full Text


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Article Info

DATE

2006-11

AUTHORS

V. I. Minkin, S. M. Aldoshin, V. N. Komissarov, I. V. Dorogan, Yu. A. Sayapin, V. V. Tkachev, A. G. Starikov

ABSTRACT

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. More... »

PAGES

2032-2055

References to SciGraph publications

Identifiers

URI

http://scigraph.springernature.com/pub.10.1007/s11172-006-0547-x

DOI

http://dx.doi.org/10.1007/s11172-006-0547-x

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1047888624


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