Asymmetric Hydrogenation of Phenanthridines with Chiral Boranes

The asymmetric hydrogenation of N-heteroarenes provides an efficient method for the synthesis of optically active cyclic secondary amines.In this paper,we described an asymmetric hydrogenation of phenanthridines using a chiral mono-alkene-derived borane.A variety of dihydrophenanthridines were furnished in high yields with up to 93%ee.The current catalytic system was very sensitive for the steric hindrance of phenanthridines.Bulky substituents at one phenyl group of phenanthridines were required to obtain the high enantioselectivity.But large substituents on the carbon of the C=N bonds would diminish the reactivity sharply.

Facile, one-pot synthesis of new phenanthridine derivatives through 1,4-dipolar cycloaddition of phenantridine, activated acetylenes, and aromatic aldehydes

A facile, one-pot synthesis of new phenanthridine derivatives by a three-component reaction between phenantridine, dialkyl acetylenedicarboxylates（DAADs）, and aromatic aldehydes is described. The reaction is characterized by mild conditions, high selectivity, and tolerance to various functional groups.

Practical and modular construction of benzo[c]phenanthridine compounds

Here,we describe a general and modular strategy for the rapid assembly of benzo[c]phenanthridine(BCP)derivatives using homogeneous gold catalysis.Notably,in contrast to traditional methods based on the specially preformed substrates that have an inherent preference for the formation of this class of compounds with limited flexibility,this protocol is achieved via a selectively intramolecular cascade of a diazo-tethered alkyne and subsequently an intermolecular cyclization with a nitrile to facilitate the successive C–N and C–C bonds formation.This methodology uses readily available nitriles as the nitrogen source to deliver the products in good yield with excellent functional group compatibility.A preliminary anti-tumor activity study of these generated products exhibits high anticancer potency against five tumor cell lines,including He La,Mel624,SW-480,8505C,LAN-1.Besides,we report a catalyst-controlled intermolecular cycloaddition/intramolecular insertion of the substrate with a fulvene to provide fused polycarbocycles containing a seven-membered ring.

Synthesis and Crystal Structure of 6-Cyclohexyl-8-methylphenanthridine

The target compound Ⅳ (C_(20)H_(21)N) was synthesized through four-step reactions and structurally determined by single-crystal X-ray diffraction.The crystal of compound Ⅳ is in the orthorhombic system,space group Fdd2 with a=41.178(19),b=30.389(8),c=4.8182(17)Å,β=90°,C_(20)H_(21)N,M_(r)=275.38,D_(c)=1.213g/cm^(3),V=6029(4)Å^(3),Z=16,F(000)=2368,μ(Mo Ka)=0.527 mm^(-1),T=240(2) K,2200 independent reflections with 1233 observed ones (I>2σ(I)),R=0.1285 and w R=0.2589 with GOF=1.050 (R=0.2058 and w R=0.3055for all data).A one-dimensional interaction model of the title compound was formed by one kind of π-π interactions between the two phenyl rings of the adjacent molecules at upper and lower levels.The inhibition to the strand transfer process of HIV-1 integrase of the target compound was also evaluated.