Solvent-free synthesis of novel highly functionalized dihydroanthra[1,2-b] furan-6,11-dione derivatives

Synthetic Communications

Volumn 38, Issue 16, 2008, Pages 2731-2740

  Nourmohammadian, Farahnaz ^a   Gholami, Mahnaz Davoodzadeh ^a  

^a INSTITUTE FOR COLOR SCIENCE AND TECHNOLOGY   (Iran)

Author keywords

1,5 dihydroxyanthraquinone; Acetylenic ester; C vinylation; Hydroxyfuran; Solvent free; Triphenylphosphine

Indexed keywords

ANTHRAQUINONE DERIVATIVE; DICARBOXYLIC ACID; DIETHYL 2 [1,5 DIHYDROXY 6 [3 METHOXY 1 (METHOXYCARBONYL) 3 OXO 2(TRIPHENYL LAMBDA 5 PHOSPHANYLIDENE)PROPYL] 9,10 DIOXO 9,10 DIHYDRO 2 ANTHRACENYL] 2 BUTANEDIOATE; DIETHYL 2 [2,7 DIHYDROXY 3 [2 METHOXY 2 OXO 1 (TRIPHENYL LAMBDA 5 PHOSPHANYLIDENE)ETHYL] 6,11 DIOXO 6,11 DIHYDROANTHRA[1,2 BETA]FURAN 8 YL] 2 BUTANEDIOATE; DIISOPROPYL 2 [1,5 DIHYDROXY 6 [3 METHOXY 1 (METHOXYCARBONYL) 3 OXO 2(TRIPHENYL LAMBDA 5 PHOSPHANYLIDENE)PROPYL] 9,10 DIOXO 9,10 DIHYDRO 2 ANTHRACENYL] 2 BUTANEDIOATE; DIISOPROPYL 2 [2,7 DIHYDROXY 3 [2 METHOXY 2 OXO 1 (TRIPHENYL LAMBDA 5 PHOSPHANYLIDENE)ETHYL] 6,11 DIOXO 6,11 DIHYDROANTHRA[1,2 BETA]FURAN 8 YL] 2 BUTANEDIOATE; DIMETHYL 2 [1,5 DIHYDROXY 6 [3 METHOXY 1 (METHOXYCARBONYL) 3 OXO 2(TRIPHENYL LAMBDA 5 PHOSPHANYLIDENE)PROPYL] 9,10 DIOXO 9,10 DIHYDRO 2 ANTHRACENYL] 2 BUTANEDIOATE; DIMETHYL 2 [2,7 DIHYDROXY 3 [2 METHOXY 2 OXO 1 (TRIPHENYL LAMBDA 5 PHOSPHANYLIDENE)ETHYL] 6,11 DIOXO 6,11 DIHYDROANTHRA[1,2 BETA]FURAN 8 YL] 2 BUTANEDIOATE; SOLVENT; TRIPHENYLPHOSPHINE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG STRUCTURE; DRUG SYNTHESIS; HEATING; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 49949107411     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910802222621     Document Type: Article

References (21)

1. Hunger, K. Industrial Dyes, 3rd ed.; Wiley-VCH: Weinheim, 2003.
2. Zollinger, H. Color Chemistry, Wiley-VCH: Weinheim, 2003.
3. Santis, D. D.; Moresi, M. Production of alizarin extracts from Rubia tinctorum and assessment of their dyeing properties. Ind. Crops Prod. 2007, 26, 151-162.
4. Nagia, F. A.; El-Mohamedy, R. S. R. Dyeing of wool with natural anthraquinone dyes from Fusarium oxysporum. Dyes and Pigments 2007, 75, 550-555.
5. Lown, J. (Ed.). Anthracycline and Anthracenedione-Based Anticancer Agents; Elsevier: Amsterdam, 1988.
6. Hsu-Shan, H.; Hui-Fen, C.; Jeng-Fong, C.; Pen-Fong, Y.; Chi-Wei, T.; Wei-Ren, J. Synthesis and cytotoxicity of 9-alkoxy-1,5-dichloroanthracene derivatives in murine and human cultured tumor cells. J. Arch. Pharm. 2002, 335, 481-486.
7. Cambie, R. C.; Rutledge, P. S.; Woodgate, P. D. Synthetic anthracyclines from anthraquinones. Aust. J. Chem. 1992, 45, 483-512.
8. Singh, D. N.; Verma, N.; Raghuwanshi, S.; Shukla, P. K.; Kulshreshtha, D. K. Antifungal anthraquinones from Saprosma fragrans. Bioorg. Med. Chem. Lett. 2006, 16, 4512-4514.
9. Zhou, X.; Song, B.; Jin, L.; Hu, D.; Diao, C.; Xu, G.; Zou, Z.; Yang, S. Isolation and inhibitory activity against ERK phosphorylation of hydroxyanthraquinones from rhubarb. Bioorg. Med. Chem. Lett. 2006, 16, 563-568.
10. Comini, L. R.; Nunez Montoya, S. C.; Sarmiento, M.; Cabrera, J. L.; Arguello, G. A. Characterizing some photophysical, photochemical, and photobiological properties of photosensitizing anthraquinones. J. Photochem. Photobiol. A-Chem. 2007, 188, 185-191.
11. Mishra, A. K.; Jacob, J.; Mullen, K. Synthesis of aminocarbazole- anthraquinone fused dyes and polymers. Dyes Pigments. 2007, 75, 1-10.
12. Kyung Kim, T.; Son, Y. A. Synthesis of a novel bridge compound having hetero-bi-functional reactive groups, part 2: The characteristics of disperse dyeings. Dyes Pigments 2005, 66, 27-32.
13. Chairungsi, N.; Jumpatong, K.; Suebsakwong, P.; Sengpracha, W.; Phutdhawong, W.; Buddhasukh, D. Electrocoagulation of quinone pigments. Molecules 2006, 11, 514-522.
14. Zaggout, F. R.; Fattah, A.; Qarraman, A.; Zourab, S. M. Behavior of immobilized alizarin red S into sol-gel matrix as pH sensor. Mat. Lett. 2007, 61, 4192-4195.
15. Namsrai, N.; Yoshinari, T.; Itoh, H.; Nagasaka, S. I.; Kuriyama, Y.; Sakamoto, M.; Takahashi, Y. Polarization dependence of absorption and luminescence spectra of a 1,5-dihydroxyanthraquinone single crystal. J. Phys. Soc. Jap. 2006, 75, 44703-44711.
16. Choi, J. R.; Jeoung, S. C.; Cho, D. W. Time-resolved anisotropy study on the excited-state intramolecular proton transfer of 1-hydroxyanthraquinone. Bull. Korean Chem. Soc. 2003, 24, 1675-1679.
17. Zaitsev, A. B.; Vasil'tsov, A. M.; Schmidt, E. Y.; Mikhaleva, A. I.; Morozova, ,L. V.; Afonin, A. V.; Ushakov, I. A.; Trofimov, B. A. O-Vinyldiaryl-and O-vinylaryl(hetaryl)ketoximes: A breakthrough in Ovinyloxime chemistry. Tetrahedron. 2002, 58, 10043-10046.
18. Weissermel, K.; Arfe, H. J. Industrial Organic Chemistry, 3rd ed; Weinheim: VCH, 1997.
19. Wilson, K.; Adams, D. J.; Rothenberg, G.; Clark, J. H. Comparative study of phenol alkylation mechanisms using homogeneous and silica-supported boron trifluoride catalysts. J. Mol. Catal. A: Chem. 2000, 159, 309-314.
20. Yavari, I.; Nourmohammadian, F. Synthesis of highly functionalized stable heterocyclic phosphorus ylides: Cycloaddition reaction between conjugated phosphorus ylides and alkyl propiolates. Tetrahedron. 2000, 56, 5221-5224.
21. Yavari, I.; Moradi, L. A synthesis of isoxazoles through the reaction of activated acetylenes and alkyl 2-nitroethanoates in the presence of triphenylphosphine. Treahedron Lett. 2006, 47, 1627-1629.