41892-84-6

Upstream product

• 108-98-5 thiophenol 
• 762-42-5 dimethyl acetylenedicarboxylate 
• 68486-71-5 3-Morpholino-4-(phenylthio)sydnon 
• 84548-77-6 5-bromomethyl-2,3-dicarboxymethylbenzothiophene 
• 71-43-2 benzene 
• 68486-73-7 4-(Phenylthio)-3-piperidinosydnon 
• 53709-32-3 3-(Dimethylamino)-4-(phenylthio)sydnon 
• 69045-46-1 3-Phenylthio-1-aza-2,5-diazoniaspiro<4,5>deca-1,3-dien-2,4-diolat 
• 78365-65-8 3,3-Dimethyl-5-phenylthio-2-aza-1,3-diazoniacyclopentadien-1,4-diolat 

Downstream Products

• 1429655-43-5 (E)-methyl 2-styrylbenzo[b]thiophene-3-carboxylate 
• 1222858-92-5 methyl 2-(4-methoxyphenyl)benzo[b]thiophene-3-carboxylate 
• 1429655-45-7 C₁₆H₁₁NO₄S 
• 63675-96-7 2-(4-methoxy-phenyl)benzo[b]thiophen-3-yl 4-methoxyphenyl ketone 
• 5732-24-1 benzothiophene-2,3-dicarboxylic anhydride 
• 22913-25-3 methyl benzothiophene-3-carboxylate 

Relevant academic research and scientific papers

Direct benzothiophene formation via oxygen-triggered intermolecular cyclization of thiophenols and alkynes assisted by manganese/PhCOOH

An intermolecular oxidative cyclization between thiophenols and alkynes for benzothiophene formation has been established. A variety of multifunctional benzothiophenes are synthesized. In addition, we demonstrated that the obtained benzothiophenes can be

Thiol mediated 5-(π-endo)ortho vinyl radical cyclizations

The radical reaction of benzenethiol with alkynes 1a-o carried out at 154 °C affords a mixture of thiol/alkyne adduct 3 and benzothiophene 5, deriving from vinyl radical intermediates 2 through hydrogen abstraction and 5-(π-endo)(orthocyclization onto the

alpha-Phenylpropionic Acid Derivatives. Synthesis and Dethiation of 5-Benzoylbenzothiophene-3-carboxylic Acid

The total synthesis of the title compound 8 started with p-thiocresol which was acylated with oxalyl chloride to give compound 1.This product underwent a condensation reaction with chloroacetic acid under basic conditions yielding compound 2.Two different synthetic pathways were used to convert compound 2 into the title compound 8.The first consisted in decarboxylation of 2 to 3, which was then converted to the ester 4, which was brominated and the product 5 was subjected to a Friedel-Craft's reaction with benzene.The resulting benzyl derivative 6 was oxidized to the benzoyl stage i.e. compound 7, which was finally hydrolyzed to 8.The second pathway was similar to the first one so that the steps of esterification, bromination, Friedel-Craft's alkylation and oxidation started with the dicarboxylic acid 2.Thus compounds 12-16 were obtained, and the last product was decarboxylated to 8.The yields in both procedures were similar.Finally, the dethiation of compound 8 with Raney nickel afforded compounds 18, 19 and 20.

Neue thermische Reaktionen von 3 Amino- und 4-(Phenylthio)sydnonen mit Alkinen und Alkenen

As cyclic azomethine imines, the 3-aminosydnones 1a - c, e - h react at 80 - 160 deg C with dimethyl acetylenedicarboxylate via non-isolable primary adducts 3 with evolution of carbon dioxide to produce the 1-aminopyrazoles 2a, c, d, e - h (yield 70 - 2percent) of table 1.Surprisingly, the analogous reactions of 1a, e proceed also with formation of the 1,2-oxazin-6-one derivative 4 as a result of an amino nitrene elimination from the primary adduct 3 which competes with the carbon dioxide elimination.In some cases, the 1-methylpyrazole 13, the pyridinetetracarboxylic ester18, as well as the benzothiophene derivative 19 are also isolable.Furthermore, the reactions of 1 with diphenylacetylene, styrene and dimethyl fumarate are described.

New Unusually Photochemical Reactions of 3-Aminosydnones

The light-induced reactions of the 3-amino-4-(phenylthio)sydnones 1a - d surprisingly produce beside diphenyl disulfide the sydnone isomers 11a - d with 2-aza-1,3-diazoniacyclopentadiene-1,4-diolate structure in 2,3 - 27percent yields.The photoreactions of the sydnones 1a, c in the presence of dimethyl acetylenedicarboxylate proceed with formation of the photoisomers 11a or 11c (17percent), the benzothiophene derivative 14 (9 - 7percent), the (phenylthio)fumaric ester 15 (5percent) as well as the pyrazole derivatives 13a (18percent) or 13c (8percent), respectively.The latter are results of a thermal cycloaddition reaction of the photochemically generated nitrile imine intermediate of type 9 to dimethyl acetylenedicarboxylate.Beside 14 (30 - 43percent), the same pyrazole derivatives 13a, c are obtained on irradiation of the sydnone isomers 11a or 11c in the presence of dimethyl acetylenedicarboxylate, respectively.The analogous photoreaction of the system 1d/dimethyl acetylenedicarboxylate produces 11d (0.6percent) and 13d (1.8percent) in low yields.