52019-85-9

Upstream product

• 60-29-7 diethyl ether 
• 103-72-0 phenyl isothiocyanate 
• 1623-99-0 phenyl sodium 
• 71-43-2 benzene 
• 77-78-1 dimethyl sulfate 
• 636-04-4 N-Phenylbenzothioamide 
• 74-88-4 methyl iodide 
• 10181-56-3 2,2,4,4-tetramethylcyclobutane-1,3-dithione 
• 10181-59-6 2,2,4,4-tetramethyl-3-thioxocyclobutanone 
• 2168-78-7 methyl dithiobenzoate 
• 622-37-7 Phenyl azide 
• 93-98-1 N-phenyl benzoyl amide 

Downstream Products

• 111905-37-4 (μ-(phenyl)CN(phenyl))(μ-methylthiolate)diiron hexacarbonyl 

Relevant academic research and scientific papers

Attempted synthesis of 2-azetidinones via ester enolate condensation reactions with imines and thioimidates

Reaction of the imines 1 and ethyl isobutyrate in the presence of LDA yields β-lactams 2, whereas thioimidate 4 with the same enolate gives the substituted products 5. When phosphorous containing heterocyclic compound 9 is treated with the enolate of ethyl isobutyrate, a mixture of substituted products 10 and 11 is produced. Mechanistic details of these reactions are described.

115. 1,3-Dipole mit Zentralem S-Atom aus der Umsetzung von Aziden mit Thiocarbonyl-Verbindungen: Eine unerwartete MeS-Wanderung im Abfangprodukt eines 'Thiocarbonyl-aminids' mit Dithiobenzoesaeure-methylester

Reaction of PhN3 with O-methyl thiobenzoate (11a) and thioacetate (11c) as well as with the dithio esters 11b, d at 80 deg C yields the corresponding imidates and thioimidates 12 (Scheme 3).The formation of 12 is rationalized by a 1,3-dipolar cycloaddition of the azide and the C=S group followed by successive elimination of N2 and S.In the three-component reaction of 11b, PhN3, and the sterically crowded thioketone 1a, 1,2,4-trithiolane 13a and 1,4,2-dithiazolidine 3a are formed in addition to 12b (Scheme 4).The heterocycles 13 and 3a are trapping products of 1a and 'thiocarbonyl-aminide' 5a and 'thiocarbonyl-amidine' 2a (Ar= Ph), respectively (Scheme 6).These 1,3-dipoles are formed as reactive intermediates.Surprisingly, in the presence of catalytic amounts of acids, the major product is the (methyldithio)cyclobutyl thioimidate of type 14 (Scheme 5), formed by an acid-catalyzed MeS migration in dithiazolidine 17.A reaction mechanism is proposed in Scheme 7.

Synthesis and cytotoxic activity on islets of Langerhans of benzamide thiosemicarbazone derivatives

Eleven 1-(4-substituted α-arylaminobenzylidene)thiosemicarbazides 1 and the related semicarbazones 2 were synthesized and tested in vitro for their inhibitory effects on the islets of Langerhans. Only the thiosemicarbazones 1 suppressed the insuline and g