Stannic Chloride–Iodine: An Efficient Reagent for Regioselective Synthesis of Furan–Fused Heterocycles
摘要:
SnCl4-I-2-mediated cyclization of ortho-cyclohexenyl phenol and ortho-cyclohexenyl enol derivatives of coumarin, uracil, dimedone, and pyrone at room temperature for 1 h give the linear cyclized products in 78-90% yield, which, on treatment with 10% Pd-C at 250 degrees C for 1-2 h, afford corresponding aromatized products in 80-84% yield.
A number of ortho-cyclohexenyl phenols 2(a-i) have been cyclised by treatment with one equivalent of m-chloroperoxybenzoic acid in refluxing benzene for 4 h to furnish linearly fused 1-hydroxy-1,2,3,4,4a,9a-hexahydrodibenzofurans 3 (a-i) (70-80%) and bicyclic 3-hydroxy-1,3-ethanochromans 4(a-f) (10-20%). Products 3(a-i) were oxidised with 2,3-dichloro-5,6-dicyano-1 ,4-benzoquinone (excess) in refluxing dry xylene for 6 h to give 2,3-dihydrodibenzofuran-1 (2H)-ones 6(a-i) (85-95%).
Hexamethylene tetramine hydrotribromide is found to be superior to pyridine hydrotribromide when compared with the rate of reaction and chemoselectivity for the regioselective cyclisation of a number of ortho-cyclohexenyl phenols 1(a-j) to 3-bromo-2,4-propano-chromans 2(a-j).
Majumdar, K C; Kundu, A K, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 6, p. 605 - 606