A Review on Synthetic Approaches of Phenanthridine

Abstract

The phenanthridine family is widely found in medicinal chemistry and material science because of the biological activity and the presence in a variety of significant natural products and synthetic dye-stuffs. The phenanthridine has many clinical application like anticancer agent, antibacterial, antiprotozoal, pharmaceutically, and optoelectronic properties. Many methods have been reported for the synthesis of phenanthridine and phenanthridine alkaloids such as Pd catalyzed C-C bond forming. Reaction involving C-H activation , Radical, Microwave-assisted , transition metal catalyzed, one- pot cascade, benzyne mediated, photochemical, hypervalent iodine promoted ,etc. Here we summarized the literature data from 2014 to present concerning a novel or improved synthetic approaches.

Visible-Light-Mediated Annulation/Thiolation of 2-Isocyanobiaryls with Disulfides to Organoylthiophenanthridines Derivatives

“…Petroleum ether/ethyl acetate (40:1); 1 H NMR (400 MHz, CDCl 3 ) δ 8.44 (d, J = 8.0 Hz, 1H), 8.31 (s, 1H), 7.67−7.65 (m, 2H), 7.58−7.48 (m, 6H), 7.37 (s, 1H), 3.23 (s, 3H), 2.61 (s, 3H); 13 C{ 1 H} NMR (101 MHz, CDCl 3 ) δ 159. 8,143.3 140.1,136.6,135.8,134.8,133.4,131.8,128.7,128.7,128.5,128.4,125.6,124.1,123.0,122.2,120.6,26.1,…”

“…Petroleum ether/ethyl acetate (20:1); 1 H NMR (400 MHz, CDCl 3 ) δ 8.71 2H),1H),1H),1H),7.80 (d,J = 7.6 Hz,2H),2H),4H),4H); 13 C{ 1 H} NMR (101 MHz,CDCl 3 ) δ 159.2,144.1,140.4,140.2,135.1,131.7,130.5,130.1,129.5,129.1,129.0,128.7,128.6,128.0,127.6,126.4,125.9,123.9,123.1,123.1,122.1. 22 2-Methyl-6-(phenylthio)phenanthridine(3ka 8,142.5,136.2,134.6,132.6,130.9,130.7,130.4,129.2,128.9,128.3,127.4,126.0,125.7,123.1,122.4,121.7,. White solid, 52.0 mg, 85%, Mp: 120−122 °C.…”

“…Numerous bioactive molecules contain the basic configuration of phenanthridine, such as calothrixin B, sanguinarine, ethidium bromide, trisphaeridine, HIF 1α-transcription inhibitor, and lycobetaine (Scheme ). Due to their excellent biological activities, more and more attention has been paid to develop efficient methods for their generation (such as transition-metal-mediated cyclization or metal-free annulation reactions) or functionalization including alkylation, , carboxamidation, trifluoromethylation, arylthiodifluoromethylation, phosphorylation, and other modifications …”

Photocatalytic Synthesis of 6-Phosphorylated Phenanthridines from 2-Isocyanobiphenyls via Radical C−P and C−C Bond Formation

“…Great progress and developments have been made in the synthetic strategies of phenanthridine derivatives via C-H bond activation, radical addition cyclization, photochemical catalysis, isocyanide chemistry, etc. [10][11][12]. The transformation proceeded in the absence or presence of various transition-metal catalysts, such as Pd, Mn, Cu, Ru, Ir, Rh, Fe, Ni, and so on.…”

“…The transformation proceeded in the absence or presence of various transition-metal catalysts, such as Pd, Mn, Cu, Ru, Ir, Rh, Fe, Ni, and so on. The functionalization mainly focused on the 6-position of phenanthridine [10][11][12], including trifluoromethylation, difluoromethylation, arylation, alkylation, alkynylation, acylation, sulfonylation, phosphorylation, difluoromethylphosphonation, benzylation, trichooromethylation, thiolation, etc.…”