An expeditious and environmentally friendly synthesis of 3-substituted isocoumarins using microwave irradiation

Natural Product Research

Volumn 22, Issue 13, 2008, Pages 1120-1127

  Khan, Khalid Mohammed ^a   Ahmed, Sumbul ^a   Khan, Zulfiqar Ali ^a   Rani, Mubeen ^a   Perveen, Shahnaz ^b   Voelter, Wolfgang ^c  

^a UNIVERSITY OF KARACHI   (Pakistan)

^b PCSIR LABORATORIES COMPLEX   (Pakistan)

^c UNIVERSITY OF TÜBINGEN   (Germany)

Author keywords

3 substituted isocoumarins; Homophthalic acid; Microwave irradiation

Indexed keywords

3 (1 NAPHTHYL)ISOCOUMARIN; 3 (2 BROMOPHENYL)ISOCOUMARIN; 3 (2 CHLOROPHENYL)ISOCOUMARIN; 3 (2 METHYLPHENYL)ISOCOUMARIN; 3 (2 NAPHTHYL)ISOCOUMARIN; 3 (2 NITROPHENYL)ISOCOUMARIN; 3 (3 CHLOROPHENYL)ISOCOUMARIN; 3 (3 METHYLPHENYL)ISOCOUMARIN; 3 (3 NITROPHENYL)ISOCOUMARIN; 3 (3,4,5 TRIMETHOXYPHENYL)ISOCOUMARIN; 3 (4 BROMOPHENYL)ISOCOUMARIN; 3 (4 CHLOROPHENYL)ISOCOUMARIN; 3 (4 METHOXYPHENYL)ISOCOUMARIN; 3 (4 METHYLPHENYL)ISOCOUMARIN; 3 (4 NITROPHENYL)ISOCOUMARIN; 3 NONANYLISOCOUMARIN; 3 OCTYLISOCOUMARIN; 3 PHENYLISOCOUMARIN; 3 UNDECYLISOCOUMARIN; CHLORIDE; COUMARIN DERIVATIVE; ISOCOUMARIN DERIVATIVE; SOLVENT; UNCLASSIFIED DRUG;

ANALYTIC METHOD; ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; INFRARED RADIATION; MASS SPECTROMETRY; MICROWAVE RADIATION; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; ULTRAVIOLET RADIATION;

ISOCOUMARINS; MICROWAVES; MOLECULAR STRUCTURE; PHTHALIC ACIDS;

EID: 54249161869     PISSN: 14786419     EISSN: 14786427     Source Type: Journal    
DOI: 10.1080/14786410601082318     Document Type: Article

References (40)

1. Barry, RD (1964) Isocoumarins Development since 1950. Chem. Rev., 64, pp. 229-260.
2. Hill, RA (1986) Naturally occurring isocoumarins. Progress in the Chemistry of Organic Natural Products, 49, pp. 1-78. Springer-Verlag, New York
3. Napolitano, E. (1997) The synthesis of isocoumarins over the last decade. A review. Org. Prep. Proced. Int., 29, pp. 631-664.
4. Myata, R., Yoshioka, T., Kumagai, HK, Nishida, H., Okamoto, R. Sawa, T. et al. (1993) Preparation of anticancer isocoumarins. Chem. Abst., 119, p. 138971z.
5. Geol, RK, Maiti, RN, Manickam, M. and Ray, AB (1997) Antiulcer activity of naturally occurring pyrano-coumarin and isocoumarinms and their effect on prostanoid synthesis using human colonic mucosa. Indian J. Experimen. Biol., 35, pp. 1080-1083.
6. Hernandez, CL, Sarabia, AC and Gravalos, GD (1996) Antitumor isocoumarins. Chem. Abstr., 125, p. 273726n.
7. Lee, JH, Park, YJ, Kim, HS, Hong, YS, Kim, K-W and Lee, JJ (2001) Anti-angiogenic activities of novel isocoumarins, AGI-7 and sescandelin. J. Antibiot., 54, p. 466.
8. Nagai, H., Tsuchida, T., Isshiki, K. and Takeuchi, T. (2001) Preparation of isocoumarins as intermediates for isocoumarin-3-ylacetic acid-type immunomodulator and angiogenesis inhibitor. Chem. Abst., 134, p. 326406c.
9. Powers, JC, Kam, CM, Oweida, SW and Ku, DN (1991) Preparation of isocoumarins with basic substituents as serine proteases inhibitors, anticoagulants and anti-inflammatory inhibitors. Chem Abstr, 114, p. 143145.
10. Scott, PM, Van Walbeek, W. and MacLean, WM (1971) Cladosporin, a new antifungal metabolite from Cladosporium cladosporioides. J. Antibiot., 24, pp. 747-755.
11. Waitz, JA and Drube, CG (1972) Antifungal agents. Ann. Rep. Med. Chem., 7, pp. 109-118.
12. Okazaki, T. (1989) Cosmetics containing isocoumarin derivatives as ultraviolet light absorbers. Chem. Abstr., 110, p. 141262p.
13. Harper, WJ and Powers, JC (1984) 3-Alkoxy-7-amino-4-chloroisocoumarins: a new class of suicide substrates for serine proteases. J. Am. Chem. Soc., 106, pp. 7618-7619.
14. Meyer Jr, EF, Presta, LG and Radhakirshnan, R. (1985) Sereospecific reaction of 3-methoxy-4-chloro-7-aminoisocoumarin with crystalline porcine pancreatic elastase. J. Am. Chem. Soc., 107, pp. 4091-4093.
15. Abubakar, AB, Booth, BL and Tipping, AE (1990) Novel Diels-Alder cycloaddition involving two -unsaturated esters in the formation of isocoumarins from the reaction of ethylpropynoate with 3,4-bis(trifluoromethyl)furan. J. Fluorine Chem., 47, pp. 353-359.
16. Ahmad, HB, Rama, NH, Hussain, M., Hussain, MT, Qasim, MM Hameed, S. et al. (2003) Synthesis of 3-aryl- and 3-aryl-3,4-dihydroisocoumarins. Indian J. Chem., 42, pp. 611-615.
17. Bhakta, C. (1985) Synthesis of 3-acyl-and-3-arylisocoumarins. Indian J. Chem., 24, pp. 428-431.
18. Haworth, RD, Pindred, HK and Jafferies, PR (1954) Chebulinic acid. Part III. Oxidation of ellagic and flavellagic Acids and the synthesis of some isocoumarin derivatives. J. Chem. Soc., pp. 3617-3625.
19. Kendall, JK and Fisher, TH (1989) An improved synthesis of 6,8-dimethoxy-3-methylisocoumarin, a fungal metabolite precursor. J. Org. Chem., 54, pp. 4218-4220.
20. Kinder, MA, Kopf, J. and Margaretha, P. (2000) Solid state photochemistry of isocoumarins and isothiocoumarines. Tetrahedron, 56, pp. 6763-6767.
21. Krohn, K. and Vitz, J. (2004) Total synthesis of premithramycinone H and related anthrapyran antibiotics. Euro. J. Org. Chem., pp. 209-219.
22. Kundu, NG, Pal, M. and Nandi, B. (1998) Palladium-catalysed heteroannulation with terminal alkynes: Synthesis of phthalides. J. Chem. Soc. Perkin Transact., 1, pp. 561-568.
23. Larock, RC, Varaprath, S., Lau, HH and Fellows, CA (1984) Synthesis of isocoumarins via thallation-olefination of benzoic acids. J. Chem. Soc., 106, pp. 5274-5284.
24. Liao, H-Y and Cheng, C-H (1995) Snythesis of isocoumarins from o-iodobenzoic acid and terminal acetylene mediated by palladium complexes and zinc chloride. J. Org. Chem., 60, pp. 3711-3716.
25. Mal, D., Bandyopadhyay, M., Ghorai, SK and Datta, K. (2000) Total synthesis of coriandrin and 7-demethylcoriandrin via a new synthesis of isocoumarins. Tetrahedron Lett., 41, pp. 3677-3680.
26. Mali, RS and Babu, KN (1998) Reactions of 3-(1-hydroxyalkyl)phthalides with acids: Synthesis of (Z)-3-alkylidenephthalides and 3-alkyl-8-hydroxyisocoumarins. J. Org. Chem., 63, pp. 2488-2492.
27. Mali, RS, Jagtap, PG, Patil, SR and Pawar, PN (1992) Novel AlCl3 catalysed synthesis of naturally occuring 8-hydroxy-3-methyl-3,4-dihydroisocoumarins. J. Chem. Soc. Chem. Commun., pp. 883-884.
28. Minami, T., Nishimoto, A., Nakamura, Y. and Hanaoka, M. (1994) Synthesis of 3-substituted isocoumarins through acyloxypalladation of o-alkenylbenzoic acids. Chem. Pharma. Bull., 42, pp. 2665-2668.
29. Nozawa, K., Yamada, M., Tsuda, Y., Kawai, K. and Nakajima, S. (1981) Synthesis of antifungal isocoumarins. II. Synthesis and antifungal activity of 3-substituted isocoumarins. Chem. Pharma. Bull., 29, pp. 2491-2495.
30. Rose, A., Buu-Hoi, NP and Jacquignon, P. (1965) Oxygen heterocycles. Part XI. The condensation of phenols with homopthalic acids and anhydrides. J. Chem. Soc., pp. 6100-6104.
31. Warnell, JL and Shriner, RL (1957) The ozonolysis of indene in ethanol. J. Am. Chem. Soc., 79, pp. 3165-3167.
32. Zenner, JM and Larock, RC (1999) Palladium-catalyzed, asymmetric hetero- and carboannulation of allenes using functionally-subsituted aryl and vinylic iodides. J. Org. Chem., 64, pp. 7312-7322.
33. Kappe, CO (2004) Controlled microwave heating in modern organic synthesis. Angewandte Chemie International Edition: English, 43, pp. 6250-6284.
34. Khan, KM, Iqbal, S., Lodhi, MA, Maharvi, GM, Zia-Ullah Choudhary, MI et al. (2004) Biscoumarin: New class of urease inhibitors, economical synthesis and activity. Bioorgan. & Med. Chem., 12, pp. 1963-1968.
35. Khan, KM, Maharvi, GM, Khan, MTH, Perveen, S., Choudhary, MI and Atta-ur-Rahman (2005) A facile and improved synthesis of sildenafil (Viagra) analogs through solid support microwave irradiation possessing tyrosinase inhibitory potential, their conformational analysis and molecular dynamics simulation studies. Mol. Divers., 9, pp. 15-26.
36. Khan, KM, Maharvi, GM, Perveen, S., Khan, MTH, Abdel-Jalil, RJ Shah, STA et al. (2005) Synthesis of methyl ether analogs of sildenafil (Viagra) possessing tyrosinase inhibitory potential. Chem. Biodivers., 2, pp. 470-476.
37. Khan, KM, Saify, ZS, Khan, MZ, Hayat, S., Begum, S. Noor, F. et al. (2004) Synthesis, antifungal, and phytotoxic effects of some benzopyrone derivatives. Nat. Prod. Res., 18, pp. 21-27.
38. Khan, KM, Saify, ZS, Khan, MZ, Zia-Ullah, Choudhary, MI Atta-ur-Rahman et al. (2004) Synthesis of coumarin derivatives with cytotoxic, antibacterial and antifungal activity. J. Enzym. Inhib. Med. Chem., 19, pp. 373-379.
39. Khan, KM, Zia-Ullah, Rani, M., Perveen, S., Haider, SM Choudhary, MI et al. (2004) Microwave-assisted synthesis of 2,5-disubstituted-1,3,4-oxadiazoles. Lett. Org. Chem., 1, pp. 50-52.
40. Khan, KM, Ahmed, S., Khan, ZA, Rani, M., Perveen, S. Choudhary, MI et al. (2005) First microwave-assisted synthesis of 3-substituted isocoumarins. Lett. Org. Chem., 2, p. 534.