Solid-phase synthesis of proline analogs via a three component 1,3-dipolar cycloaddition

Selective Cleavage of Isopropyl Aryl Ethers by Aluminum Trichloride†

“…Concentration of the appropriate fractions then gave compound 18 (4.10 g, 87%) (Rf ) 0.4, CH2Cl2) as a cream powder, mp 60-61°C: IR (KBr disk, cm -1 ) 1763, 1748, 1586; 1 H NMR (300 MHz) δ 7.18 (s, 1H), 6.66 (s, 1H), 4.47 (septet, J ) 5.7 Hz, 1H), 3.83 (s, 3H), 2.34 (s, 3H), 1.36 (d, J ) 5.7 Hz, 6H); 13 C NMR (75 MHz) δ 168. 8, 148.7, 148.1, 144.8, 120.9, 109.7, 77.7, 71.6, 56.4, 21.8, 21. c. 3-Isopropoxy-2-methoxybenzaldehyde (20). A magnetically stirred solution of 3-hydroxy-2-methoxybenzaldehyde (21) 19 (400 mg, 2.6 mmol) and potassium carbonate (1.26 g, 9.1 mmol) in DMF (6 mL) was treated in one portion with 2-bromopropane (296 µL, 3.2 mmol).…”

Synthesis of New Azo Compounds Based on N-(4-Hydroxypheneyl)maleimide and N-(4-Methylpheneyl)maleimide

“…Small molecules and macromolecules containing imide groups exhibit great electrical properties, good solubility in polar media, resistance to hydrolysis and high thermal stability [ 1 , 2 , 3 , 4 , 5 , 6 , 7 , 8 ]. Due to their excellent properties many efforts have been made to produce different compounds containing imide groups consisting of two carbonyl groups bound to nitrogen.…”

Solid-Phase Parallel Synthesis of Drug-Like Artificial 2H-Benzopyran Libraries

“…3-Formyl-4-hydroxybenzoyl moiety loaded resin 89 was introduced by amide formation of amine resin 88 and 3-formyl-4-hydroxybenzoyl chloride ( 90 ) in the presence of 2,6-lutidine. The various Mitsunobu reactions [102,103,104,105,106] were explored for a polymer-bounded aldoxime containing a phenol-tethered alkyne 94 . A Mitsunobu reaction between polymer-bounded phenol 89 and propargyl alcohol 91 with R 2 and R 3 using sulfonamide betaine 92 gave disubstituted resins 93 .…”