Base catalyzed dimerization of ω-formyl-2-hydroxyacetophenones

Year 2016, Volume: 3 Issue: 2, 159 - 166, 16.06.2016

Magdy Ahmed Ibrahim Salah Sayed Ibrahim

https://doi.org/10.18596/jotcsa.10789

Cited By: 1

Abstract

Refluxing ω-formyl-2-hydroxyacetophenones 1 in ethanol containing triethylamine as a basic catalyst produced the dimerized product identified as 2-(2-hydroxyaryl)-4H,5H-pyrano[2,3-b]chromen-5-ones 2. Meanwhile, heating ω-formyl-2-hydroxyacetophenones 1 in 2M aqueous sodium hydroxide solution afforded another type of dimeric product identified as 3-[2-(2-hydroxy-5-substituted benzoyl)vinyl]-6-substituted-4H-chromen-4-ones 3. The proposed mechanisms were discussed. The mode of dimerization of ω-formyl-2-hydroxyacetophenones 1 depends on the type of catalyst used and the reaction conditions. Structures of the synthesized compounds were deduced on the basis of their analytical and spectral data.

References

• Nikolaev VA, Ivanov AV, Shakhmin AA, Sieler J, Rodina LL. The first examples of cycloadditions of 2-diazo-1,3-dicarbonyl compounds to aromatic thioketones. Tetrahedron Letters. 2012 Jun;53(24):3095–9. DOI: 10.1016/j.tetlet.2012.04.036.
• Ohtsuka Y, Uraguchi D, Yamamoto K, Tokuhisa K, Yamakawa T. Syntheses of 2-(trifluoromethyl)-1,3-dicarbonyl compounds through direct trifluoromethylation with CF3I and their application to fluorinated pyrazoles syntheses. Tetrahedron. 2012 Mar;68(12):2636–49. DOI: 10.1016/j.tet.2012.01.075.
• Ng EPJ, Wang Y-F, Hui BW-Q, Lapointe G, Chiba S. Orthogonal synthesis of pyrroles and 1,2,3-triazoles from vinyl azides and 1,3-dicarbonyl compounds. Tetrahedron. 2011 Oct;67(40):7728–37. DOI: 10.1016/j.tet.2011.08.006.
• Wang J-L, Liu B-K, Yin C, Wu Q, Lin X-F. Candida antarctica lipase B-catalyzed the unprecedented three-component Hantzsch-type reaction of aldehyde with acetamide and 1,3-dicarbonyl compounds in non-aqueous solvent. Tetrahedron. 2011 Apr;67(14):2689–92. DOI: 10.1016/j.tet.2011.01.045.
• Arcadi A, Alfonsi M, Chiarini M, Marinelli F. Sequential gold-catalyzed reactions of 1-phenylprop-2-yn-1-ol with 1,3-dicarbonyl compounds. Journal of Organometallic Chemistry. 2009 Feb;694(4):576–82. DOI: 10.1016/j.jorganchem.2008.12.013.
• Wang Y, Dong D, Yang Y, Huang J, Ouyang Y, Liu Q. A facile and convenient one-pot synthesis of polysubstituted thiophenes from 1,3-dicarbonyl compounds in water. Tetrahedron. 2007 Mar;63(12):2724–8. DOI: 10.1016/j.tet.2006.12.090.
• Hassanin H, Ibrahim M, Alnamer Y. Synthesis and antimicrobial activity of some novel 4-hydroxyquinolin-2(1H)-ones and pyrano[3,2-c]quinolinones from 3-(1-ethy1-4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl)-3-oxopropanoic acid. Turkish Journal of Chemistry. 2012;36:682–99. DOI: 10.3906/kim-1111-14.
• Ismail M, Othman E, Mohamed H. Synthesis and Cyclization Reactions with Quinolinyl Keto Esters I. Chemical Reactivity of Quinolinyl beta-Keto Ester and Quinolinyl alpha,beta-Unsaturated Ketones. Chemical Papers. 2005;59(2):117–26. URL: http://www.chempap.org/file_access.php?file=592a117.pdf.
• Ibrahim SS. Uses of o -Hydroxybenzoylacetone in the Synthesis of Some Substituted 2-Methylchromones, Chelating Agents, and Related Materials. Industrial & Engineering Chemistry Research. 2001 Jan;40(1):37–9. DOI: 10.1021/ie9906767.
• Széll T, Sohár P, Horváth G. On the chemistry of α-formyl-2-hydroxyacetophenone. Liebigs Annalen. 1995 Nov;1995(11):2043–4. DOI: 10.1002/jlac.1995199511286.
• Ibrahim M. Ring transformation of chromone-3-carboxylic acid under nucleophilic conditions. ARKIVOC. 2008;xvii:192–204. URL: http://www.arkat-usa.org/get-file/27587/.
• Kostka K. Chromones. IV. Cyclization of ω-formyl-o-hydroxyacetophenone and o-hydroxyphenyl-1,3-diketones. Roczniki Chemii. 1966;40:1861.
• Schönberg A, Sina A. On Visnagin and Khellin and Related Compounds. A Simple Synthesis of Chromone. Journal of the American Chemical Society. 1950 Aug;72(8):3396–9. DOI: 10.1021/ja01164a022.
• Ibrahim M, Ali T. Ring opening and ring closure reactions of chromone-3-carboxylic acid: unexpected routes to synthesize functionalized benzoxocinones and heteroannulated pyranochromenes. Turkish Journal of Chemistry. 2015;39:412–25. DOI: 10.3906/kim-1410-41.