3-Hydroxyphthalimidines from o-cyanobenzophenones

A Catalyst‐Free Cascade Reaction for the Selective Assembly of 3‐Hydroxyisoindolinones on Water

“…It turned out that increasing the polarity of the solvent seems beneficial for this transformation, providing a remarkable improvement in the reaction yield. Specifically, excellent yields were obtained in CH 3 CN (93%) and CH 3 NO 2 (91%), and high yields were observed in DMSO (84%) and DMF (86%) (entries [10][11][12][13]. In particular, the reaction between substrates 1 aa and 2 aa could also take place well in polar protic solvents such as MeOH and EtOH, affording the product 3 aa in 62% and 75% yields, respectively (entries 14 and 15).…”

“…1H),1H),1H),7.41 (d,J = 7.6 Hz,1H),2H), 08 (m, 1H), 7.08-7.04 (m, 2H), 6.99 (d, J = 8. 2 Hz,1H),1H),6.83 (d,J = 7.4 Hz,2H),4.83 (d,J = 16.5 Hz,1H),4.67 (d,J = 16.5 Hz,1H), 4.42 (s, 1H), 3.91 (s, 3H), 3.43 (d, J = 13.9 Hz, 1H), 3.31 (d, J = 13.9 Hz, 1H); 13 C NMR (150 MHz, CD 3 CN) δ 167. 84, 157.74, 147.69, 136.16, 132.71, 132.42, 131.13, 130.29, 129.42, 128.98, 128.63, 127.58, 127.29, 124.07, 123.11, 121.16, 111.35, 92.32, 56.19, 43.67, 37.81 [17] colorless oil (67.8 mg, yield 94%).…”

“…73,163.66 (d,147.60,142.87 (d,135.97,132.89,132.25,131.03,130.92 (d,130.36,128.66,127.64,124.89,124.01,123.15,115.64 (d,114.48 (d,92.45,43.54,43.04;LRMS (ESI) [17] white solid (63.6 mg, yield 92%), mp 189-191°C. 1 13,161.15 (d,146.94,135.12,135.08,131.62,131.17,130.03 (d,129.92,129.09,127.52,126.44,123.17,122.01,114.69 73, 147.60, 142.40, 135.93, 134.44, 132.92, 132.24, 131.01, 130.80, 130.37, 128.90, 128.66, 127.83, 127.64, 127.58, 123.99, 123.15, 92.47, 43.48, 43. 66, 147.59, 139.41, 135.98, 132.87, 132.29, 132.08, 131.22, 131.01, 130.34, 128.66, 127.63, 123.98, 123.11, 121.10, 92.46, 43.51, 42.92 69, 147.61, 140.00, 138.17, 135.98, 132.87, 132.29, 131.40, 131.02, 130.34, 128.67, 127.63, 123.99, 123.12, 92.46, 43.54, 43. 19,156.13 (d,147.00,136.82,135.02,131.81,131.01,129.92,129.85,129.18,128....…”

“…57-7.52 (m, 1H), 7.51-7.47 (m, 1H), 7.44-7.37 (m, 2H), 7.12-7.05 (m, 3H), 6.99-6.94 (m, 2H), 4.57 (s, 1H), 4.31 (s, 2H), 3.50 (d,J = 13.9 Hz,1H),3.34 (d,J = 13.9 Hz,1H),2.48 (s,1H). 13 C NMR (150 MHz,CD 3 CN) δ 167.24,147.57,136.05,132.97,131.96,131.22,130.34,128.64,127.63,124.10,123.21,92.02,81.06,71.81,43.15,28.26;LRMS (ESI)…”

“…[7] Therefore, synthetic methods for the generation of 3-hydroxyisoindolinones have captured wide attention. The multi-step synthesis from o-carboxy [8] /chloroformyl [9] /ester [10] / carbonyl [11] /halide [12] /cyano [13] -phenylketones or N-acylbenzamides [14] constitutes a traditional method to diverse 3hydroxyisoindolinones, but it requires the preparation of the highly functional substrates. The addition of organometallic reagents (e. g. Grignard reagents) or other nucleophilic agents to phthalimides represents another conventional protocol to 3hydroxyisoindolinones, [15] but it has intrinsic drawbacks such as harsh reaction conditions (e. g. the requirement of anhydrous environment) and poor site-selectivity.…”