Manganese(III) acetate mediated oxidation of flavanones: A facile synthesis of flavones

Synthetic Communications

Volumn 35, Issue 20, 2005, Pages 2723-2728

  Singh, Om V ^a,b   Muthukrishnan, M ^a   Raj, Gopan ^a  

^a JAWAHARLAL NEHRU TROPICAL BOTANIC GARDEN AND RESEARCH INSTITUTE   (India)

^b UNIVERSITY OF TEXAS AT SAN ANTONIO   (United States)

Author keywords

Dehydrogenation; Flavanone; Flavone; Manganese(III) acetate; Oxidation

Indexed keywords

ACETIC ACID DERIVATIVE; FLAVANONE; FLAVONE DERIVATIVE; MANGANESE ACETATE; MANGANESE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; DEHYDROGENATION; INFRARED SPECTROSCOPY; OXIDATION; PHYTOCHEMISTRY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 27544481255     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910500214490     Document Type: Article

References (24)

1. (a) Harborne, J. B.; Williams, C. A. Advances in flavonoid research since 1992. Phytochemistry 2000, 55 (6), 481-504;
2. (b) Venkataraman, K. Flavonoids. In Flavonoids; Harborne, J. B., Mabry, T. J., Mabry, H., eds.; Chapman & Hall: London, 1975; pp. 267-295.
3. Shanker, C. G.; Mallaiah, B. V.; Srimannarayana, G. Dehydrogenation of chromanones and flavanones by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ): A facile method for the synthesis of chromones and flavones. Synthesis 1983 (4), 310-311.
4. Doshi, A. G.; Soni, P. A.; Ghiya, B. J. Oxidation of 2′- hydroxychalcones. Indian J. Chem. 1986, 25B (7), 759.
5. Mahal, H. S.; Rai, H. S.; Venkataraman, K. Synthetical experiments in the chromone group. XVI. Chalcones and flavanones and their oxidation to flavones by means of selenium dioxide. J. Chem. Soc. 1935, 866-868.
6. Mallik, U. K.; Saha, M. M.; Mallik, A. K. Cyclodehydrogenation of 2′-hydroxychalcones and dehydrogenation of flavanones using nickel peroxide. Indian J. Chem. 1989, 28B (11), 970-972.
7. Hoshino, Y.; Ohinata, T.; Takeno, N. The direct preparation of flavones from 2′-hydroxychalcones using disulfides. Bull. Chem. Soc. Jpn. 1986, 59 (7), 2351-2352.
8. (a) Singh, O. V.; Kapoor, R. P. Dehydrogenation of flavanones to flavones using thallium(III) acetate (TTA). Tetrahedron Lett. 1990, 31 (10), 1459-1462;
9. (b) Varma, R. S.; Varma, M. Oxidation of flavanones with thallium(III) nitrate (TTN). A convenient route to flavones. Synth. Commun. 1982, 12 (12), 927-930.
10. (a) Prakash, O.; Pahuja, S.; Moriarty, R. M. Synthesis of flavones from the hypervalent iodine oxidation of flavanones using [hydroxy(tosyloxy)iodo] benzene in methanol. Synth. Commun. 1990, 20 (10), 1417-1422;
11. (b) Prakash, O.; Tanwar, M. P. Hypervalent iodine oxidation of flavanones: convenient and useful syntheses of flavones and isoflavones. J. Chem. Res. Synop. 1995 (6), 213.
12. Cavill, G. W. K.; Dean, F. M.; McGookin, A.; Marshall, B. M.; Robertson, A. Oxidation of chromanones and flavanones with lead tetraacetate. J. Chem. Soc. 1954, 4573-4581.
13. (a) Demir, A. S.; Jeganathan, A. Selective oxidation of α,β-unsaturated ketones at α′-position. Synthesis 1992 (3), 235-247;
14. (b) Melikyan, G. G. Manganese(III)-mediated reactions of unsaturated systems. Synthesis 1993 (9), 833-850;
15. (c) Snider, B. B. Manganese(III)-based oxidative free-radical cyclizations. Chem. Rev. 1996, 96 (1), 339-363;
16. (d) Melikyan, G. G. Carbon-carbon bond-forming reactions promoted by trivalent manganese. In Organic Reactions; Paquette, L. A., ed.; Wiley: New York, 1997; Vol. 49, pp. 427-625.
17. Demir, A. S.; Camkerten, N.; Akgun, H.; Tanyeli, C.; Mahasneh, A. S.; Watt, D. S. Oxidation of aryl alkyl ketones to α-acyloxy, α-(camphorsulfonyloxy), or α-hydroxy derivatives using manganese(III) acetate in combination with carboxylic acids or (IS)-(+)-10-camphorsulfonic acid. Synth. Commun. 1990, 20 (15), 2279-2289.
18. Tsuruta, T.; Harada, T.; Nishino, H.; Kurosawa, K. The α-chlorination of aryl ketones with manganese(III) acetate in the presence of chloride ion. Bull. Chem. Soc. Jpn. 1985, 58 (1), 142-145.
19. Singh, O. V.; Kapil, R. S. A general method for the synthesis of isoflavones by oxidative rearrangement of flavanones using thallium(III) perchlorate. Indian J. Chem. 1993, 32B (9), 911-915.
20. Khanna, M. S.; Singh, O. V.; Garg, C. P.; Kapoor, R. P. Oxidation of flavanones using thallium(III) salts: A new route for the synthesis of flavones and isoflavones. J. Chem. Soc., Perkin Trans. 1 1992 (19), 2565-2568 and references cited therein.
21. Thakar, K. A.; Gill, C. H. Synthesis and screening of some 1,3-propanediones and flavones. J. Indian Chem. Soc. 1983, 60 (7), 668-670.
22. A receptor complex. J. Med. Chem. 1999, 42 (21), 4343-4350.
23. A receptor devoid of intrinsic activity. Pharmacol. Biochem. Behav. 2000, 65 (2), 313-320.
24. Keane, D. D.; Maratha, K. G.; O'Sullivan, W. L; Philin, E. M.; Simons, R. M.; Teague, P. C. Configuration and conformation of 3-arylidene-flavanones. J. Org. Chem. 1970, 35 (7), 2286-2290.