596805-18-4

Upstream product

• 21615-34-9 2-Methoxybenzoyl chloride 
• 579-75-9 2-Methoxybenzoic acid 
• 624-92-0 Dimethyldisulphide 
• 51674-10-3 N,N-diethyl-2-methoxybenzamide 

Downstream Products

• 3781-90-6 4-methoxybenzo[b]thiophene 
• 849193-31-3 1-(3-hydroxy-4-methoxybenzo[b]thiophen-2-yl)-3-phenylprop-2-en-1-one 

Relevant academic research and scientific papers

Photostability of 4,4′-dihydroxythioindigo, a mimetic of indigo

The photochemical properties of indigo, a widely used industrial dye, has attracted both experimentalists and theoreticians from the beginning. Especially the high photostability of indigo has been the subject of intensive research. Recently, it was propo

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

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

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.

Studies in sulfur heterocycles. Part 16:1,2 synthesis of [1]benzothieno[3,2-b]pyrans via tandem reactions from 2,3-dihydrobenzo[b]thiophene-3(2H)ones

Sequential treatment of N,N-diethyl-2-methylsulfanyl aryl amides with LDA and p-anisaldehyde, 1-naphthaldehyde and cinnamaldehyde afforded the corresponding thioaurones. Heating the thioaurones derived from cinnamaldehyde, above 200°C resulted in electrocyclic ring closure and sigmatropic shift in tandem to give substituted [1]benzothieno[3,2-b]pyran. Treatment of N,N-diethyl-2-methylsulfanyl-5-methoxy benzamide and crotonaldehyde gave 4-methyl-8-methoxy[1]benzothieno[3,2-b]pyran via conjugate nucleophilic addition and ring closure in one pot. Possible mechanistic pathways are discussed.

Application of directed metallation in synthesis, part 2: An expedient synthesis of methoxybenzo[b]thiophenes

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.