Chemistry of Heterocyclic Compounds, Vol. 42, No. 7, 2006
LETTERS TO THE EDITOR
NOVEL APPLICATION OF THE
BAYLIS–HILLMAN REACTION
V. V. Trifonov1, V. I. Goncharov2, and A. V. Aksenov1
Keywords: 2,3'-biquinoline, 2-vinylquinolines, 1',2'-dihydro-2,3'-biquinolines, cyclization.
Earlier [1] we developed a novel method for synthesis of 1',4'-dihydro-2,3'-biquinolines, based on
cyclization of 2-vinylquinolines. Methods for synthesis of 1',2'-dihydro-2,3'-biquinolines 3 directly from
quinolines have not been previously described. In this paper, we report on the synthesis of compounds 3 based
on the Baylis–Hillman reaction [2].
RCHO
DABCO
THF
N
N
H2N
R
N
1
2a–c
N
R
N
H
3a–c
DABCO = 1,4-diazabicyclo[2.2.2]octane, 2, 3 a R = Me, b R = Ph, c R = 1-C10H7
Synthesis of Compounds 3a-c (General Procedure). A mixture of compound 1 (0.12 g, 0.5 mmol) and
the corresponding aldehyde (0.6 mmol) was boiled for 1.5 h in dry THF (15 ml). Then 1,4-diazabicyclo-
[2.2.2]octane (0.01 g, 0.1 mmol) was added and it was allowed to stand for 26 days. Then it was poured into
water (50 ml) and extract with benzene (3 × 20 ml). The solvent was evaporated. The residue was
chromatographed, collecting the first colored fraction.
2'-Methyl-1',2'-dihydro-2,3'-biquinoline (3a). Yield 29%; mp 138-139°C (alcohol) (mp 138-139°C
[3]), Rf 0.44 (Silufol UV-254, ethyl acetate–hexane, 1:1). The 1H NMR spectrum matches that given in [3].
2'-Phenyl-1',2'-dihydro-2,3'-biquinoline (3b). Yield 51%; mp 207-209°C (alcohol) (mp 207-209°C
[3]). Rf 0.32 (Silufol UV-254, ethyl acetate–hexane, 1:1). 1H NMR spectrum matches that given in [3].
2'-(1-Naphthyl)-1',2'-dihydro-2,3'-biquinoline (3c). Yield 46%; mp 166-167°C (benzene)
(mp 166°C-167°C [3]), Rf 0.77 (Silufol UV-254, ethyl acetate). 1H NMR spectrum matches that in [3].
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1
2
Stavropol State University, Stavropol 355009, Russia; e-mail: k-biochem-org@stavsu.ru. Stavropol
State Medical Academy, Stavropol 355017, Russia; e-mail: sgma@statel.stavropol.ru. Translated from Khimiya
Geterotsiklicheskikh Soedinenii, No. 7, pp. 1105-1106, July, 2006. Original article submitted October 20, 2005.
0009-3122/06/4207-0955©2006 Springer Science+Business Media, Inc.
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