Palladium-Catalyzed sp³ C–H Nitration of 8-Methylquinolines

Abstract

Palladium-catalyzed nitration of 8-methylquinolines with t-BuONO to give 8-(nitromethyl)quinolines in moderate to excellent yields has been developed involving an sp(3) C-H bond activation. The resulting (nitromethyl)quinolines could be selectively reduced to (1,2,3,4-tetrahydroquinolin-8-yl)methanamines by NaBH4 in the presence of a catalytic amount of NiCl2·6H2O.

Tuning the Electronic, Photophysical and Charge Transfer Properties of Small D-a Molecules Based on Thienopyrazine-Terthienyls by Changing the Donor Fragment: A DFT Study

“…34 This fact has as consequence the lowest E g evaluated for TPR1 (E g =2.275 eV) in comparison with the gaps for thieno [3,4-b]pyrazine analogues (E g =2.75 eV), 10 and 5,7-dithien-2-ylthieno [3,4-b]pyrazine (E g =2.38 eV), [35][36] obtained at the B3LYP/6-311G(d,p) and B3LYP/6-31G(d,p) levels of theory respectively; and the experimentally reported for heterocyclic-thiophene-conjugated polymers with electron donoracceptor fragment (E g =2.47 eV). 37 The band gap value calculated for TPR4 (E g =2.069 eV) is in agreement with previous theoretical reports (E g =2.16 eV). 38 Also, note from Table 2, that the substitution of α-hydrogen in the thiophene ring in TPR1 by different electron-rich donor groups (p-dimethoxyphenyle, carbazole and fluorene), is causing that E g in the neutral state decreases about 0.2 eV and the values of the HOMO and LUMO are being modified.…”

tert‐Butyl Nitrite (TBN), a Multitasking Reagent in Organic Synthesis

“…All the products were obtained in good to moderate yields. The final product can be selectively reduced using NaBH 4 which shows the synthetic potential of the present methodology (Scheme ) …”

“…The final product can be selectively reduced using NaBH 4 which shows the synthetic potential of the present methodology (Scheme 71). [104] Li group in the same year reported an itrative cyclization of N-aryl imines (99)t og ive dehydrogenative access to 3-nitroindoles (100)u nder am etal-free condition. This transformation goes through the oxidative cleavage of multiple CÀHb onds, nitration,c yclization,a nd isomerization sequence.…”

1‐Phenyl‐1,2‐benziodoxol‐3‐(1H)‐one as Synthon for Phthalide Synthesis through Pd‐Free, Base‐Free, Sonogashira‐Type Coupling Cyclization Reaction

“…Thin-layer chromatography (TLC) was performed with silica HSGF254 plates. Melting points were determined with a digital (Z)-3-Benzylideneisobenzofuran-1(3H)-one (6a): [36] [27] [29a] [37] 1-Phenyl-1,2-benziodoxol-3-(1H)-one (1; 331 mg, 1.0 mmol), and [27] (Z)-3-(4-Fluorobenzylidene)isobenzofuran-1(3H)-one (6f): [36] (Z)-3-Pentylideneisobenzofuran-1(3H)-one (6g): [38] [39] SO 4 , the reaction mass was mechanically shaken to achieve better mixing; the color of the resulting mass can vary from pale yellow to brown depending on the intensity of mixing. After all H 2 SO 4 was added, magnetic stirring was continued for 30 min at room temperature, the mixture was cooled to 5°C, and CH 2 Cl 2 (4 mL) and the corresponding ArH (10 mmol) was added.…”