55786-24-8Relevant academic research and scientific papers
Bicyclic 1,2,3-triazolium ionic liquids: Synthesis, characterization, and application to rutaecarpine synthesis
Tseng, Ming-Chung,Cheng, Hui-Ting,Shen, Meng-Jane,Chu, Yen-Ho
scheme or table, p. 4434 - 4437 (2011/10/05)
Starting with commercial reagents, bicyclic 1,2,3-triazolium ionic liquids [b-3C-tr][NTf2] (1) and [b-4C-tr][NTf2] (2) were synthesized in four steps with high overall isolated yields of 68% and 76%, respectively. Since the C-5 hydrogen is acidic, under basic condition ionic liquids 1 and 2 were readily methylated with methyl iodide to afford chemically stable ionic liquids 7 and 8 at room temperature (88% and 82%, respectively). Ionic liquid 1 was used as the ionic solvent to demonstrate its usefulness for the synthesis of rutaecarpine, a natural product.
Photoaddition of 4(3H)-Quinazolinone Derivatives to Olefins: Effects of the 2-Substituent
Kaneko, Chikara,Kasai, Kouichi,Katagiri, Nobuya,Chiba, Takuo
, p. 3672 - 3681 (2007/10/02)
The photochemical behavior of 3-(3-butenyl)-4(3H)-quinazolinone (2a) and its 2-chloro (2b) and 2-trifluoromethyl derivatives (2c) was examined in methanol at a variety of wavelengths (254, 300, and 350 nm).The intramolecular 2+2 photoadducts (10 and 14) were obtained only when 2c and its higher methylene homologue (13) were irradiated.Though the 2-unsubstituted quinazolone (2a) was photostable, its 2-chloro derivative (2b) afforded the cyclized product (4) via homolytic fission of the C-Cl bond.An enhancement of the photocycloaddition reactivity of the C=N bond in the quinazolone ring by introduction of a trifluoromethyl group was also demonstrated by the formation of the intermolecular adducts from 2-trifluoromethyl-4(3H)-quinazolinone (1c) by irradiation in the presence of olefins.The reactions due to C-N bond fission of the azetidine ring in these adducts are also described.Finally, by utilizing photo-induced C-Cl bond fission as found in 2b, rutecarpine (26) was synthesized by irradiation of 2-chloro-3--4-(3H)-quinazolinone.Keywords-photochemical reaction; 3-(ω-alkenyl)-4(3H)-quinazoline; 2+2 photocycloaddition; wavelength dependency; azetidine; rutecarpine; vasicinone; 3-trifluoromethyl-4(3H)-quinazoline; photoarylation
A New Synthesis of Rutecarpine
Moehrle, Hans,Kamper, Christa,Schmid, Renate
, p. 990 - 995 (2007/10/02)
1,2,3,4-Tetrahydro-β-carboline (1) reacts with 2-nitrobenzyl chloride to yield the tertiary amine 2, which on reduction of the nitro group and dehydrogenating cyclization yields the pentacyclic amidine 4.Oxidation of 4 produces a mixture of rutecarpine (5) and the dehydrogenation compound 6, which are separated by chromatography.
