61736-72-9Relevant academic research and scientific papers
2-(2,1-Benzoxazol-3-yl)-3,5-dimethoxyphenol and 3-phenyl-2,1-benzoxazole
Howie,Jabbar, Abdul,Lewis, John R.,Nizami, Shaikh S.,Ritchie, Craig F.
, p. o516-o519 (2007/10/03)
The title compounds, C15H13NO4, (I), and C13H9NO, (II), are produced, along with the corresponding anilines, by the reduction of the appropriate o-nitrobenzophenones. In (I), the planar benzisoxazole and phenol fragments are tilted relative to one another by a rotation of 53.02 (14)° about the bond joining them, and the molecules are linked into chains by phenol O-H...N and phenyl C-H...O oxazole hydrogen bonds. The cell of (II) (space group 12/c) contains eight molecules in general positions, four more in the 2b sites, with twofold axial symmetry that induces a degree of disorder, and a further four as centrosymmetric pairs of complete molecules, each with an occupancy of one-half. The relative tilt of the planar fragments varies slightly from one molecule to another but is much less than that in (I), ranging from 8.8 (8) to 12.58 (15)°.
RUTACEOUS CONSTITUENTS-13 A BIOMIMETIC SYNTHESIS OF ACRONYCINE
Adams, Joyce H.,Brown, P. Margaret,Gupta, Padma,Khan, M. Shafig,Lewis, John R.
, p. 209 - 218 (2007/10/02)
A biomimetic synthesis of the anti-tumor active alkaloid acronycine (7; R=R'=Me) has been obtained by cyclisation of 6-(2-methylaminobenzoyl)-5,7-dimethoxy-2,2-dimethylchromene (11; R=R'=Me); isoacronycine (20; R=R'=Me) was also produced.In an analogous manner the aminochromene (11; R=H, R'=Me) gave a mixture of des-N-methylacronycine (7; R=H, R'=Me) and des-N-methylisoacronycine (20; R=H, R'=Me).The aminochromenes were best synthesised by condensation of lithio-5,7-dimethoxy-2,2-dimethylchromene (22; R=Li) with N-methylisatoic anhydride (26) or with 2-methyl-3,1-benzoxazin-4-one (21).The relevance of this synthetic route to the biogenesis of acridone alkaloids is discussed.
