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DOI: 10.1055/s-2002-35233
A Simple and Efficient Synthesis of 2-Methyl-2-trifluoromethylchroman-4-ones from 2-Trifluoromethyl-4H-chromen-4-imines and Malonic Acid
Publikationsverlauf
Publikationsdatum:
04. November 2002 (online)
Abstract
N-Benzyl-2-trifluoromethyl-4H-chromen-4-imines and malonic acid on heating in anhydrous dioxane afford 2-trifluoromethyl-2-methylchroman-4-ones in ∼60% yield. 2-Methyl-2-trifluoromethyl-4-oxochromane-6-carbaldehyde and 2-methyl-2-trifluoromethyl-4-oxochromane-6-carboxylic acid, the fluorinated analogues of natural lactarochromal and the corresponding acid, were obtained by the oxidation of 2,6-dimethyl-2-trifluoromethylchroman-4-one with K2S2O8.
Key words
N-benzyl-2-trifluoromethyl-4H-chromen-4-imines - malonic acid - 2-methyl-2-trifluoromethylchroman-4-ones - oxidation - fluorinated analogues of natural compounds
- 1a
Sosnovskikh VYa.Usachev BI. Mendeleev Commun. 2000, 240 - 1b
Sosnovskikh VYa.Usachev BI. Russ. Chem. Bull. 2001, 50: 453 - 1c
Sosnovskikh VYa.Usachev BI. Russ. Chem. Bull. 2001, 50: 1426 - 1d
Sosnovskikh VYa.Vorontsov II.Kutsenko VA. Russ. Chem. Bull. 2001, 50: 1430 - 3
Sosnovskikh VYa.Usachev BI. Mendeleev Commun. 2002, 75 - 4a
Wallace TW. Tetrahedron Lett. 1984, 25: 4299 - 4b
Clarke PD.Fitton AO.Suschitzky H.Wallace TW.Dowlatshahi HA.Suschitzky JL. Tetrahedron Lett. 1986, 27: 91 - 4c
Saengchantara ST.Wallace TW. Tetrahedron 1990, 46: 3029 - 5a
Ellis GP. Chromenes, Chromanones, and Chromones, In The Chemistry of Heterocyclic Compounds Vol. 31:Ellis GP. Wiley; New York: 1977. p.1-10 - 5b
Banerji A.Goomer NC. Indian J. Chem. 1984, 23B: 885 - 5c
Dawood KM.Fuchigami T. J. Org. Chem. 2001, 66: 7691 - 6
Ayer WA.Trifonov LS. J. Nat. Prod. 1994, 57: 839 - 7a
Kamat VP.Asolkar RN.Kirtany JK. J. Chem. Res. (S) 2001, 41 - 7b
Ohshima E.Otaki S.Sato H.Kumazawa T.Obase H.Ishii A.Ishii H.Ohmori K.Hirayama N. J. Med. Chem. 1992, 35: 2074 - 8
Ngo LV.Pham TVC. Phytochemistry 1981, 20: 485 - 9
Brown NMD.Nonhebel DC. Tetrahedron 1968, 24: 5655
References
Sosnovskikh, V. Ya.; Usachev, B. I. Tetrahedron 2002, in press.