Efficient synthesis of deoxybenzoins from chalcones

Synthetic Communications

Volumn 37, Issue 5, 2007, Pages 661-665

  Mathew, Paulson ^a   Mathew, Daliya ^a   Asokan, C V ^a  

^a MAHATMA GANDHI UNIVERSITY   (India)

Author keywords

Chalcones; Deformylation; Deoxybenzoins; Epoxides; Rearrangement

Indexed keywords

ALDEHYDE; BENZENE DERIVATIVE; CHALCONE DERIVATIVE; DEOXYBENZOIN DERIVATIVE; ETHYLENEDIAMINE; LEWIS ACID; TETRAHYDROFURAN; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; REACTION ANALYSIS; SUBSTITUTION REACTION; SYNTHESIS;

EID: 33847136097     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910601130967     Document Type: Article

References (21)

1. Kabalka, G. W.; Ju, Y.; Wu, Z. A new titanium tetrachloride mediated annulation of aryl-substituted carbonyl compounds with alkynes: A simple and highly efficient method for the regioselective synthesis of polysubstituted naphthalene derivatives. J. Org. Chem. 2003, 68, 7915-7917.
2. (a) Kim, Y.-W.; Brueggemeier, R. W. A convenient one-pot synthesis of 2-(alkylthio)isoflavones from deoxybenzoins using a phase transfer catalyst. Tetrahedron Lett. 2002, 43, 6113-6115;
3. (b) Kim, T. Y.; Kim, H. S.; Chung, Y. M.; Kim, J. N. Facile synthesis of 2,4,5-trisubstituted oxazole derivatives from deoxybenzoins. Bull. Korean Chem. Soc. 2000, 21, 673-674;
4. (c) Garcia, A.; Lete, E.; Villa, M. J.; Dominguez, E.; Badia, D. M. A simple direct approach to 1-substituted 3-arylisoquinolines from deoxybenzoins and nitriles. Tetrahedron 1988, 44, 6681-6686.
5. (a) Gupton, J. J.; Krumpe, K. E.; Burnham, B. S.; Webb, T. M.; Shuford, J. S.; Sikorski, J. A. The application of vinylogous iminium salt derivatives to a regiocontrolled and efficient relay synthesis of lukianol a and related marine natural products. Tetrahedron 1999, 55, 14515-14522;
6. (b) Gupton, J. T.; Clough, S. C.; Miller, R. B.; Lukens, J. R.; Henry, C. A.; Kanters, R. P. R.; Sikorski, J. A. The application of vinylogous iminium salt derivatives to the synthesis of Ningalin B hexamethyl ether. Tetrahedron 2003, 59, 207;
7. (c) Churruca, F.; SanMartin, R.; Tellitu, I. Dominguez, E. Palladium-catalyzed crylation of ketone enolates: An expeditious entry to tamoxifen-related l,2,2-triarylethanones. Org. Lett. 2002, 4, 1591-1594;
8. (d) Villa, M. J.; Dominguez, E.; Lete, E. On the Leuckart reaction of deoxybenzoins - isolation and characterization of 2,3,4,5-tetraarylpyridine derivatives. Heterocycles 1986, 24, 1943.
9. (a) Wähälä, K.; Hase, T. A. Expedient synthesis of polyhydroxyisoflavones. J. Chem. Soc., Perkin Trans. 1991, 3005;
10. (b) Dyke, S. F.; Brown, D. W.; Sainsbury, M.; Hardy, T. The synthesis of 5-hydroxyberbine derivatives. Tetrahedron 1971, 27, 3495-3502.
11. (a) Al-Maharik, N. I.; Kaltia, Seppo, A. A.; Mutikainen, I.; Wähälä, K. Synthesis of C-C-bridged bis-isoflavones. J. Org. Chem. 2000, 65, 2305-2308;
12. (b) Paventi, M.; Hay, A. S. Facile preparation of deoxybenzoins via a novel synthesis of enamines. Tetrahedron Lett. 1991, 32, 1617-1620;
13. (c) Han, Y.; Fang, L.; Tao, W.-T.; Huang, Y.-Z. Tetraorganogallate complexes in organic chemistry: A novel, efficient and versatile preparation of ketones from acyl chlorides. Tetrahedron Lett. 1995, 36, 1287-1290;
14. (d) Miyashita, A.; Matsuoka, Y.; Suzuki, Y.; Iwamoto, K.; Higashino, T. A new method of synthesizing deoxybenzoins from 1,3-dimethyl-2-(alpha- benzyloxybenzyl) imidazolium and 1,3-dimethyl-2-(alpha-benzyloxybenzyl) benzimidazolium iodides based on Wittig-type rearrangement. Chem. Pharm. Bull. 1997, 45, 1235-1242.
15. Mathew, P.; Asokan, C. V. Cyclization of functionalized ketene-N,S-acetals to substituted pyrroles: Applications in the synthesis of marine pyrrole alkaloids. Tetrahedron Lett. 2005, 46, 475-478.
16. Bailly, C. Lamellarins, from A to Z: A family of anticancer marine pyrrole alkaloids. Curr. Med. Chem. - Anti-Cancer Agents 2004, 4, 363-378.
17. Russell, P. B.; Csendes, E. The structures of the isomeric enols and methyl ethers of formyldesoxybenzoin. J. Am. Chem. Soc. 1954, 76, 5714-5718.
18. Zimmerman, H. E.; Singer, L.; Thyagarajan, B. S. Overlap control of carbanionoid reactions, I: Stereoselectivity in alkaline epoxidation. J. Am. Chem. Soc. 1959, 81, 108-116.
19. (a) Parker, R. E.; Isaacs, N. S. Mechanisms of epoxide reactions. Chem. Rev. 1959, 737-799;
20. (b) Naqvi, S. M.; Horwitz, J. P.; Filler, R. The rearrangement of cyclohexene oxides with magnesium bromide etherate. J. Am. Chem. Soc. 1957, 79, 6283-6286;
21. (c) House, H. O. The acid-catalyzed rearrangements of the stilbene oxides. J. Am. Chem. Soc. 1955, 70, 3070-3075.