Improved selective reduction of 3-formylchromones using basic alumina and 2-propanol

Synthetic Communications

Volumn 33, Issue 18, 2003, Pages 3225-3231

  Araya Maturana, Ramiro ^a   Heredia Moya, Jorge ^a   Pessoa Mahana, Hernán ^a   Weiss López, Boris ^a  

^a UNIVERSITY OF CHILE   (Chile)

Author keywords

[No Author keywords available]

Indexed keywords

2 PROPANOL; 3 FORMYLCHROMONE DERIVATIVE; ALUMINUM OXIDE; CHROMONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; REACTION ANALYSIS; REDUCTION; SYNTHESIS; TECHNIQUE; TEMPERATURE DEPENDENCE;

EID: 0042334788     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-120023445     Document Type: Article

References (24)

1. Ellis, G.P. Chromones, Chromanones, chapter XII, Hydroxychromones 633-689; chapter XIII Alkoxychromones, 691-748; Chapter XIV Halochromones, 749-777.
2. Ellis, G.P. Chromones, Chromanones, chapter XII, Hydroxychromones 633-689; chapter XIII Alkoxychromones, 691-748; Chapter XIV Halochromones, 749-777.
3. Ellis, G.P. Chromones, Chromanones, chapter XII, Hydroxychromones 633-689; chapter XIII Alkoxychromones, 691-748; Chapter XIV Halochromones, 749-777.
4. Ellis, G.P. Chromones, Chromanones, chapter XII, Hydroxychromones 633-689; chapter XIII Alkoxychromones, 691-748; Chapter XIV Halochromones, 749-777.
5. Ellis, G.P.; Becket, G.J.P.; Shaw, D.; Wilson, H.K. Benzopyrones. 14. Synthesis and antiallergic properties of some N-tetrazolilcarboxamides and related compounds. J. Med. Chem. 1978, 21 (11), 1120-1126.
6. Davidson, D.N.; Kaye, P.T. Chromone studies. Part 2. An efficient synthesis of N,N-dimethylchromone-2-carboxamides. Synthetic Commun. 1990, 20 (5), 727-732.
7. Refat, H.M. Heterocyclic synthesis with nitriles: synthesis of some new chromone and flavone and its utilization for the synthesis of potentially antitumorigenic policyclic chromones and flavones. Synthetic Commun. 1999, 29 (9), 1429-1436.
8. Saengchantara, S.T.; Wallace, T.W. Conjugate addition to 3-(p-tolylsulphinyl)chromone: a route to 2-substituted chromones and chiral 2-substituted chroman-4-ones. Tetrahedron 1990, 46 (18) 6553-6564.
9. Klutchko, S.; Cohen, M.P.; Shavel, J., Jr.; von Strandtmann, M. Heterocyclic synthesis with b-ketosulfoxides IV. Synthesis of 3-substituted chromones. J. Heterocyclic Chem. 1974, 11, 183-188.
10. Enders, D.; Geibel, G.; Osborne, S. Diastereo- and enantioselective total synthesis of stigmatellin A. Chem. Eur. J. 2000, 6 (8), 1302-1309.
11. Harvey, R.G.; Hahn, J.-T.; Bukowska, M.; Jackson, H. A new chromone and flavone synthesis and its utilization for the synthesis of potentially antitumorigenic policyclic chromones and flavones. J. Org. Chem. 1990, 55 (25), 6161-6166.
12. (a) Nohara, A.; Umetani, T.; Sanno, Y. A facile síntesis of chromone-3-carboxaldehyde, chromone-3-carboxylic acid, and 3-hydroxymethylchromone. Tetrahedron Lett. 1973, (22), 1995-1998;
13. (b) Nohara, A.; Umetani, T.; Sanno, Y. A Studies on antianapylactic agents-I. A facile synthesis of 4-oxo-4H-1-benzopyran-3-carboxaldehydes by Vilsmeier reagents. Tetrahedron 1974, 30, 3553-3561.
14. Rajanna, K.C.; Solomon, F.; Ali, M.M.; Saiprakash, P.K. Kinetics and mechanism of Vilsmeier-Haack sintesis of 3-formyl chromones derived from o-hydroxy aryl alkyl ketones: a structure reactivity study. Tetrahedron 1996, 52 (10), 3669-3682.
15. (a) von Strandtmann, M.; Shavel, J., Jr.; Klutchko, S.; Cohen, M.P. 3-(Hydroxymethyl)chromones. US Appl. 1974, 3, 798, 240;
16. (b) Herzig David, J.; Schumann, P.R.; Kusner, E.J.; Robichaud, L.; Giles, R.E.; Dubnick, B.; von Strandtmann, M.; Klutchko, S.; Cohen, M.P.; Shavel, J. Jr. The search for specific inhibitors of immediate hypersensitivity reactions. The activity of some chromones in various laboratory models. Monogr. Physiol. Soc. Philadelphia 1977, 1(Inmunopharmacology), 103-124.
17. (a) Posner, G.H.; Runquist, A.W.; Chapdelaine, M.J. Organic reactions at alumina surfaces, 6. isopropyl alcohol and diisopropylcarbinol on dehydrated alumina as reagents for very selective carbonyl reductions. J. Org. Chem. 1977, 42, 1202-1208;
18. (b) Posner, G.H. Organic reactions at alumina surfaces. Angew. Chem. Int. Ed. Engl. 1978, 17, 487-496.
19. Ghosh, C.K.; Bhattacharyya, S. Benzopyrans: part 40-Alumina mediated transformations of 4-oxo-4H-1-benzopyran-3-carbaldehyde, -3-carboxylic acid and their 2-methyl homologues. Indian J. Chem. Sect. B 1999, 38 (2), 166-172.
20. Ghosch, C.K.; Bhattacharyya, S. Benzopyrans: part 36-A simple synthesis of 3-hydroxymethylchromone. Indian J. Chem. Sect. B 1997, 36 (3), 267-268.
21. Aries, R. Substances derives de la Chromone. FR. Appl. 1975, 2,239,467.
22. (a) Polyakov, V.K.; Shevtsova, R.G.; Tsukerman, S.V. Dipole moments of chromone-3-aldehydes. Zh. Obshch. Khim. 1979, 49 (7), 1560-1563;
23. (b) Kononenko, L.V.; Shevtsova, R.G.; Polyakov, V.K.; Tsukerman, S.V.; Bezuglyi, V.D. Polarographic study of substituted chromone-3-aldehydes. Zh. Obshch. Khim. 1979, 49 (12), 2693-2698.
24. Fitton, A.; Frost, J.; Suschitzky, H.; Houghton, P. Conversion of 3-formylchromones into pyrrole and thiophene derivatives. Synthesis 1977, (2), 133-135.