Iodination of Aromatic Amines with Iodine and Silver Sulfate

Synthesis, radiolabeling and preliminary in vivo evaluation of multimodal radiotracers for PET imaging and targeted radionuclide therapy of pigmented melanoma

“…Derivative 48 was then treated by thionyl chloride to afford the corresponding 2-chloro-4-acyl chloride intermediate, which was The synthesis of compound 58 is displayed in Scheme 6. Methyl anthranilate (52) underwent a regiospecific electrophilic iodination in the presence of silver sulfate [38] to produce 53 in nearly quantitative yield. Compound 53 was then condensed with Meldrum's acid and triethyl orthoformate according to a protocol adapted from Krishnamurthy et al [39], to yield methyl 2-[(2,2-dimethyl-4,6-dioxo [1,3]dioxin-5-ylidenemethyl)amino]-5-iodobenzoate (54).…”

“…carboxamide(38). Starting from N-[2-(diethylamino) ethyl]-4-fluoro-6-iodoquinoline-3-carboxamide(37) (475 mg, 1.14 mmol); reaction time at reflux: 4.5 h; elution chromatography: cyclohexane/ethyl acetate, 4/6, v/v to give 38 (247 mg, 0.43 mmol) as a yellow oil.…”

Redox-Dependent Conformational Switching of Diphenylacetylenes

“…41 (8). Based on literature procedures [48,51] 3-nitroaniline 7 (0.100 g, 0.72 mmol) was added to a solution of iodine (0.183 g, 0.724 mmol) and silver(I) sulfate (0.223 g, 0.724 mmol) in methanol (15 mL). After 3 h the solution was filtered and the solid re-dissolved in aqueous sodium hydroxide (5%, 7.0 mL).…”

“…para-Substituted benzoic ester 5, which is incapable of intramolecular H-bonding, was synthesized via amide coupling of aniline 4 [31] with ferrocenoyl chloride (Scheme 2). The second control molecule, 12, was prepared from 3-nitroaniline via an adaptation of a literature route: [31] iodination of 3-nitroaniline, [48] followed by amidation, nitro-group reduction, Sonogashira coupling and coupling with ferrocenoyl chloride, afforded the desired bis(amide). The first of these, 5, estimates the chemical shift of the FcA NH in the absence of H-bonding by positioning the H-bond acceptor para to the alkyne linkage (0% control).…”

Synthesis and evaluation of a series of C5′-substituted duocarmycin SA analogs

“…Starting with the commercially available 4-substituted anilines, electrophilic aromatic iodination (1.0 equiv I 2 , 1.0 equiv Ag 2 SO 4 , EtOH, rt, 30–60 min, 30–90%)23 cleanly afforded the 4-substituted-2-iodoanilines ( 5–11 ). Treatment of the iodoanilines 5–11 with pyruvic acid (3.0 equiv), DABCO (3.0 equiv), and Pd(OAc) 2 (0.05 equiv) at 105 °C for 4 h in a thoroughly degassed solution of DMF cleanly provided the desired C5-substituted indole-2-carboxylic acids ( 12–17 , 36–86%) as a single regioisomeric product 22.…”