A practical one-pot procedure for the synthesis of N–H isoquinolones

Versatile Synthesis of 4‐Aryl Chroman and 1‐Aryl Tetralins Through Metal‐Free Reductive Arylations

“…Organic bases remained ineffective and Nalkylated products became dominant when any nucleophilic base was used (Table 1, entry-6, 7). [29][30][31][32] Molecular sieves and additives such as (nBu) 4 NI, KI were already proved detrimental for this coupling. [24c,29] Temperatures below 110°C resulted in either prolonged reaction times or poor conversions.…”

Rapid and Atom Economic Synthesis of Isoquinolines and Isoquinolinones by C–H/N–N Activation Using a Homogeneous Recyclable Ruthenium Catalyst in PEG Media

“…1‐Cyclopropyl‐3,4‐diphenylisoquinoline (3oa): [13g] White solid; m.p. 149–151 °C; 1 H NMR (500 MHz, CDCl 3 ) δ = 8.51 (d, J = 7.8 Hz, 1H), 7.67–7.55 (m, 3H), 7.38–7.34 (m, 5H), 7.27–7.21 (m, 2H), 7.20 –7.17 (m, 3H), 2.87–2.81 (m, 1H), 1.43–1.36 (m, 2H), 1.16–1.14 (m, 2H); 13 C NMR (126 MHz, CDCl 3 ) δ = 160.58, 148.54, 140.99, 137.87, 136.18, 131.43, 130.45, 129.71, 128.71, 128.10, 127.36, 127.09, 126.89, 126.85, 126.42, 126.26, 124.91, 13.64, 9.42; GC–MS (EI 70 eV) m/z (% rel.…”

“…6‐Methoxy‐3,4‐diphenylisoquinolin‐1(2 H )‐one (5ca): [13f] Off white solid; m.p. 288–290 °C; 1 H NMR (500 MHz, CDCl 3 ) δ = 9.46 (s, 1H), 8.42 (d, J = 8.6 Hz, 1H), 7.34–7.10 (m, 11H), 6.75 (d, J = 1.8 Hz, 1H), 3.74 (s, 3H); 13 C NMR (126 MHz, CDCl 3 ) δ = 163.42, 162.12, 141.04, 137.44, 135.43, 134.77, 131.64, 129.49, 129.12, 128.81, 128.49, 128.45, 127.50, 115.90, 107.55, 55.36.…”

“…6‐( tert ‐Butyl)‐3,4‐diphenylisoquinolin‐1(2 H )‐one (5da): [13f] White solid; m.p. 286–288 °C; 1 H NMR (500 MHz, CDCl 3 ) δ = 9.54 (s, 1H), 8.43 (s, 1H), 8.00 –7.18 (m, 12H), 1.25 (s, 9H); 13 C NMR (126 MHz, CDCl 3 ) δ = 160.74, 156.57, 138.70, 136.60, 134.98, 131.80, 129.88, 129.22, 128.66, 128.40, 128.33, 127.37, 127.13, 125.23, 125.08, 121.88, 118.11, 35.37, 30.97.…”

“…Due to the wealth of isoquinoline and isoquinolinone moieties, several multistep synthetic approaches are developed for their synthesis, while they are limited with numerous shortcomings like low regioselectivity, poor yields, and lengthier reaction periods in some cases. A potent alternate route to overcome these limitations was provided by annulation reactions with alkynes via ortho C–H functionalization (Scheme ). These transformations are reported with various directing groups using different transition metal catalysts with stoichiometric amount of external oxidants.…”