A Pd(ii)-catalyzed C–H activation approach to densely functionalized N-heteroaromatics related to neocryptolepine and their evaluation as potential inducers of apoptosis

Abstract

Bioactive indoloquinolines are synthesized via Pd(ii)-catalyzed intramolecular oxidative C–H alkenylation as the key step.

CO2-Involved and Isocyanide-Based Three-Component Polymerization toward Functional Heterocyclic Polymers with Self-Assembly and Sensing Properties

“…Diisocyanides 1a and 1b (Schemes S1 and S2) were prepared according to the synthetic procedures in the literature. − Inspired by the preparation method of 2-iodoaniline, , bis­(2-iodoaniline)­s 2a – 2d (Schemes S3 and S4) were prepared for the first time as far as we know.…”

CO2-Involved and Isocyanide-based Three-component Polymerization toward Functional Heterocyclic Polymers with Self-assembly and Sensing Properties

“…Diisocyanides 1a and 1b (Scheme S1 and S2) were prepared according to the synthetic procedures given in literature. [38][39][40] Inspired by the preparation method of 2iodoaniline, 41,42 bis(2-iodoaniline)s 2a-2d (Scheme S3 and S4) were prepared for the first time as far as we know.…”

Synthesis of 5-Amino-2,5-dihydro-1H-benzo[b]azepines Using a One-Pot Multibond Forming Process

“…Purification by column chromatography (ethyl acetate/petroleum ether = 1:4) gave methyl (2 E )-3-(5′-methyl-2′-[ N -( p -toluene­sulfonyl)­amino]­phenyl)­prop-2-enoate (2.68 g, 99%) as a white solid. Mp 164–166 °C (lit . 160–162 °C); R f = 0.20 (diethyl ether/petroleum ether = 1:1); 1 H NMR (400 MHz, CDCl 3 ) δ 2.32 (s, 3H), 2.35 (s, 3H), 3.77 (s, 3H), 6.10 (d, J = 15.9 Hz, 1H), 6.99 (br s, 1H), 7.12–7.19 (m, 3H), 7.23–7.26 (m, 2H), 7.50–7.57 (m, 3H); 13 C NMR (101 MHz, CDCl 3 ) δ 21.0 (CH 3 ), 21.5 (CH 3 ), 51.8 (CH 3 ), 119.7 (CH), 127.3 (2 × CH), 127.4 (CH), 128.0 (CH), 129.6 (2 × CH), 130.7 (C), 131.8 (CH), 132.1 (C), 135.9 (C), 137.4 (C), 139.4 (CH), 143.8 (C), 167.0 (C); MS (ESI) m / z 368 (MNa + , 100).…”

“…Purification by column chromatography (ethyl acetate/petroleum ether = 1:5) gave methyl (2 E )-3-(5′-fluoro-2′-[ N -( p -toluene­sulfonyl)­amino]­phenyl)­prop-2-enoate (3.94 g, 88%) as a white solid. Mp 156–158 °C (lit . 156–158 °C); R f = 0.13 (diethyl ether/petroleum ether = 1:1); 1 H NMR (400 MHz, CDCl 3 ) δ 2.36 (s, 3H), 3.78 (s, 3H), 6.07 (d, J = 15.8 Hz, 1H), 6.96 (br s, 1H), 7.06 (ddd, J = 8.8, 3 J HF = 7.7, J = 2.9 Hz, 1H), 7.14 (dd, 3 J HF = 9.2, J = 2.9 Hz, 1H), 7.19 (d, J = 8.1 Hz, 2H), 7.35 (dd, J = 8.8, 4 J HF = 5.2 Hz, 1H), 7.50 (dd, J = 15.8, 5 J HF = 1.5 Hz, 1H), 7.52 (d, J = 8.1 Hz, 2H); 13 C NMR (101 MHz, CDCl 3 ) δ 21.5 (CH 3 ), 52.0 (CH 3 ), 113.3 (d, 2 J CF = 23.5 Hz, CH), 117.9 (d, 2 J CF = 22.7 Hz, CH), 121.2 (CH), 127.3 (2 × CH), 129.7 (2 × CH), 130.6 (d, 4 J CF = 2.9 Hz, C), 130.7 (d, 3 J CF = 8.8 Hz, CH), 133.4 (d, 3 J CF = 8.4 Hz, C), 135.6 (C), 138.2 (d, 4 J CF = 2.2 Hz, CH), 144.2 (C), 161.5 (d, 1 J CF = 248.4 Hz, C), 166.5 (C); MS (ESI) m / z 372 (MNa + , 100).…”