36050-09-6Relevant academic research and scientific papers
Labelled compounds of interest as antitumour agents - VI. Isotopically efficient syntheses of [15N]-nitrothiophenecarboxamides
Shinkwin, Anne E.,Threadgill, Michael D.
, p. 1015 - 1020 (2007/10/03)
Reaction of 3-cyanothiophene with one equivalent of potassium nitrate in concentrated sulphuric acid causes nitration, concurrent with hydrolysis of the nitrile, to give 5-nitro-thiophene-3-carboxamide in high yield. Similarly, 2-cyanothiophene gives 4-nitro-thiophene-2-carboxamide and 5-nitrothiophene-2-carboxamide, benzonitrile gives 3-nitrobenzamide and 4-methylbenzonitrile gives 4-methyl-3-nitrobenzamide. Extension of this process to use of potassium [15N]-nitrate, formed from [15N]-nitric acid (95% isotopic enrichment), enables preparation of the corresponding [15N]-nitrothiophenecarboxamides in high isotopic yield.
Meisenheimer-type Adducts from Thiophene Derivates. Part 6. A Kinetic and Thermodynamic Study of Substituent Effects on the Formation of Some non-gem Adducts
Arnone, Caterina,Consiglio, Giovanni,Spinelli, Domenico,Dell'Erba, Carlo,Sancassan, Fernando,Terrier, Francois
, p. 1609 - 1612 (2007/10/02)
The rate and equilibrium constants for the formation of the Meisenheimer-type adducts from some 4-nitro-2-X- (5) or some 2-nitro-4-X-thiophenes (7) and sodium methoxide have been measured at 25 deg C in methanol or methanol-dimethyl sulphoxide mixtures.The observed stability and reactivity patterns have been interpreted in the light of the hyper-ortho relation in the thiophene ring and the special ability of the nitro group to stabilize effectively the adducts from a para-like position also.
