Mild and efficient solvent-free Friedel-Crafts acylation of reserpine

Synthetic Communications

Volumn 36, Issue 21, 2006, Pages 3203-3224

  Begum, Sabira ^a   Zehra, Syeda Qamar ^a   Siddiqui, Bina S ^a  

^a UNIVERSITY OF KARACHI   (Pakistan)

Author keywords

carboline; Acyl reserpines; Friedel Crafts acylation; Reserpine; Solidphase reaction

Indexed keywords

RESERPINE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; DRUG STRUCTURE; DRUG SYNTHESIS; FRIEDEL CRAFTS REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; SOLID PHASE SYNTHESIS; STRUCTURE ANALYSIS;

EID: 33750208282     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910600908900     Document Type: Article

References (19)

1. Nagendrappa, G. Organic synthesis under solvent-free conditions: An environmentally benign procedure-1. Resonance 2002, 59-68.
2. Brown, A. R.; Hermkens, P. H. H.; Ottenheihm, H. C. J.; Rees, D. C. Solid phase synthesis. Synlett 1998, 817-827.
3. Kaupp, G.; Schmeyers, J.; Boy, J. Waste-free solid-state synthesis with quantitative yield. Chemosphere 2001, 43, 55-61.
4. Olah, G. A. Friedel-Crafts and Related Reactions; Interscience Publishers: New York, 1964; Vol. III.
5. Vogel's Textbook of Practical Organic Chemistry, 4th ed.; ELBS/Longman: Essex, 1986pp. 770-774.
6. Salehi, P.; Khodaei, M. M.; Zolfigol, M. A.; Sirouszadeh, S. Catalytic Friedel-Crafts acylation of alkoxybenzenes mediated by aluminum hydrogensulfate in solution and solvent-free conditions. Bull. Chem. Soc. Jpn. 2003, 76, 1863-1864.
7. Kawada, A.; Mitamura, S.; Kobayashi, S. Lanthanide trifluoromethanesulfonates as reusable catalysts: Catalytic Friedet-Crafts acylation. J. Chem. Soc., Chem. Commun. 1993, 1157-1158.
8. Smith, K.; El-Hiti, G. A.; Jayne, A. J.; Butters, M. Acetylation of aromatic ethers using acetic anhydride over solid acid catalysts in a solvent free system: Scope of the reaction for substituted ethers. Org. Biomol. Chem. 2003, 1, 1560-1564.
9. Chapman, C. J.; Frost, C. G.; Hartley, J. P.; Whittle, A. J. Efficient aromatic and heteroatom acylations using catalytic indium complexes with lithium perchlorate. Tetrahedron Lett. 2001, 42, 773-775.
10. Ross, J.; Xiao, J. Friedel-Crafts acylation reactions using metal triflates in ionic liquid. Green Chem. 2002, 4, 129-133.
11. Ghiaci, M.; Asghari, J. Friedel-Crafts alkylation and acylation in the absence of solvent. Synth. Commun. 1998, 28, 2213-2220.
12. Manske, R. H. F. The Alkaloids, Chemistry and Physiology; Academic Press: New York, 1960; Vol. VII, p. 73.
13. Ulshafer, P. R.; Nugent, R. H.; Dorfman, L. 10- and 12-Acetyl reserpines. Chem. Industry 1962, 1863.
14. Negi, A. S.; Chattopadhyay, S. K.; Srivastava, S.; Bhattacharya, A. K. A simple regioselective demethylation of p-aryl methyl ethers using aluminum chloridedichloromethane system. Synth. Commun. 2005, 35, 15-21.
15. Hesse, M. Indolalkaloide; Verlag Chemie, 1974; Vol. 1, pp. 201-204.
16. 1H NMR study of four basic reserpine alkaloids. Heterocycles 1985, 23, 371-375.
17. Wenkert, E.; Chang, C.; Chawla, H. P.S.; Cochran, D. W.; Hagaman, E. W.; King, J. C.; Orito, K. General methods of synthesis of indole alkaloids 14: Short routes of construction of yohimboid and ajmalicinoid alkaloid systems and their 13C nuclear magnetic resonance spectral analysis. J. Am. Chem. Soc. 1976, 98, 3645-3655.
18. Breitmaier, E.; Haas, G.; Voclter, W. Atlas of Carbon-13 NMR Data; Heyden & Sons: London, 1979; compound no. 679, 1327, 1335, 1336, 1341, 1920.
19. Begum, S.; Hassan, S. I.; Siddiqui, B. S. A rapid, mild, efficient and solvent-free Friedel-Crafts acylation of N-acetyltetrahydroharmine. Synth. Commun. 2005, 35, 23-39.