100669-97-4Relevant academic research and scientific papers
Aluminium chloride-2-isocyanatobenzoyl chloride complex: Crystal structure and reactivity
Bigi, Franca,Sartori, Giovanni,Maggi, Raimondo,Valerio-Papa, Claudia,Marzi, Elena,Lanfranchi, Maurizio,Pellinghelli, Maria Angela
, p. 1815 - 1818 (2007/10/03)
2-Amino-2′-hydroxybenzophenones 3 have been synthesized by acylation of phenols with 2-isocyanatobenzoyl chloride 2 in the presence of aluminium trichloride. The ring-chain tautomerism of the reagent 2 promoted by Lewis acid has been established on the basis of a crystal structure analysis of the 1:1 complex formed by 2 and aluminium trichloride.
APPLICATION OF THE PHOTO-FRIES REARRANGEMENT OF ARYL N-CHLOROACETYLANTHRANYLATES AS KEY STEP IN THE SYNTHESIS OF 5-(2-HYDROXYPHENYL)-1,3-DIHYDRO-2H-1,4-BENZODIAZEPIN-2-ONES
Algarra, Felipe,Miranda, Miguel A.
, p. 2335 - 2344 (2007/10/02)
Condensation of isatoic anhydride with phenols, followed by treatment of the resulting aryl anthranylates (4) with chloroacetyl chloride gives aryl N-chloroacetylanthranylates (5).Their uv-irradiation results in photo-Fries rearrangement, to afford benzophenones (6).Direct treatment of the latter with ammonia gives rise to 1,3-quinazolines (7); by contrast, treatment of 6 with potassium iodide and subsequently with ammonia leads to 1,3-dihydro-2H-1,4-benzodiazepin-2-ones (1).
SYNTHESIS, KINETICS AND MECHANISM OF CYCLIZATION OF 1-(2-ARYLOXYCARBONYLPHENYL)-3-PHENYLTRIAZENES
Pytela, Oldrich,Bahnik, Zdenek
, p. 2692 - 2700 (2007/10/02)
Twelve substituted 1-(2-aryloxycarbonylphenyl)-3-phenyltriazenes have been synthetized and kinetics of their reactions have been measured in 52.1percent (by mass) aqueous methanol at pH 3 to 11.Plots of kobs vs pH show three regions: noncatalyzed cyclization (pH 4 to 7), acid-catalyzed splitting of the triazene chain, and base-catalyzed cyclization.The non-catalyzed cyclization exhibits a kinetic isotope effect, the reaction constant Q = 2.69 (?p-), and β1g = 1.02, which indicates a mechanism of E1cB type with intramolecular proton transfer and a transient formation of a ketene intermediate.The base-catalyzed cyclization, on the other hand, exhibits the reaction constant Q = 1.05 (?p-), β1g = 0.4, and distinct steric effects, which indicates a cyclization by BAc2 mechanism with rate-limiting formation of the tetrahedral intermediate.
