97567-49-2Relevant academic research and scientific papers
Application of directed metalation in synthesis. Part 8: Interesting example of chemoselectivity in the synthesis of thioaurones and hydroxy ketones and a novel anionic ortho-Fries rearrangement used as a tool in the synthesis of thienopyranones and thiafluorenones
Pradhan, Tarun Kanti,De, Asish,Mortier, Jacques
, p. 9007 - 9017 (2007/10/03)
Chemoselective synthesis of thioaurones or 3-hydroxy benzo[b]thiophen-2- aryl ketones, 1-hydroxy naphtho[2,1-b]thiophen-2-aryl ketones and chalcones from N,N-diethyl-ortho-methyl sulfanyl aryl amides were described. (Benzo[b]thiophen-2-yl) alkylates and (naphtho[2,1-b]thiophen-2-yl) alkylates undergo a novel anionic ortho-Fries rearrangement leading to (3-hydroxy benzo[b]thiophen-2-yl) and (1-hydroxy naphtho[2,1-b]thiophen-2-yl) alkyl ketones. The hydroxy ketones were used as intermediates in the synthesis of wide range of benzothienopyranones and thiafluorenones.
Application of directed metalation in synthesis. Part 4: Expedient synthesis of substituted benzo[b]thiophene and naphthothiophene
Mukherjee, Chandrani,Kamila, Sukanta,De, Asish
, p. 4767 - 4774 (2007/10/03)
A short, simple and inexpensive synthesis of several diversely substituted benzo[b]thiophenes and one naphthothiophene is described. The method involves introduction of methylsulfanyl group ortho- to the amide function of readily available N,N-diethylamides of aryl carboxylic acid by directed metalation. Thioindoxyls, obtained in high yields through side-chain deprotonation and cyclisation in one pot, are reduced to benzo[b]thiophene or napthothiophene.
Application of directed metallation in synthesis, part 2: An expedient synthesis of methoxybenzo[b]thiophenes
Mukherjee, Chandrani,De, Asish
, p. 325 - 327 (2007/10/03)
A short, simple and expedient synthesis of substituted benzo[b]thiophenes involving directed ortho lithiation-side-chain deprotonation-cyclisation-reduction is described. This method is a valuable improvement over earlier syntheses of the same class of compounds, both with respect to the number of steps and overall yields.
DILITHIATED SYNTHONS OF TERTIARY BENZAMIDES, PHTHALAMIDES, AND O,O'-ARYL DICARBAMATES
Mills, R. J.,Horvath, R. F.,Sibi, M. P.,Snieckus V.
, p. 1145 - 1148 (2007/10/02)
Dilithiated species 1, 2, and 3, generated by metal-halogen exchange and directed ortho metalation, undergo reaction with electrophiles to afford, in high yield, polysubstituted aromatics 6, 7, and 8 respectively; 9 is formed via a bis anionic Fries rearr
