41001-28-9Relevant academic research and scientific papers
Photocyclization synthesis of phenanthridine and its derivatives under direct dehydrogenation conditions
Zhu, Wen-Qing,Zhang, Jin,Fan, Pan,Shi, Lan-Ting,Li, Hong,Yang, Min-Ge,Li, Yang
supporting information, (2021/01/04)
A new method for synthesizing phenanthridines by photocyclization has been established. This method does not require inert gas protection, does not require transition metal catalysts and is environmentally friendly, efficient and convenient. It is proposed to use (E)-N,1-diphenylformimines as substrates to synthesize phenanthridine and its derivatives by ultraviolet light, which provides a new synthesis route for further research on the synthesis of phenanthridines by photocyclization. Eight new phenanthridine compounds were synthesized. The confirmation of their structures provides a material basis for further study of their properties and tapping of their potential for applications. The establishment of this method further broadens the synthetic pathways of phenanthridine compounds.
Metal-free tandem carbene N-H insertions and C-C bond cleavages
Chen, Pu,Nan, Jiang,Hu, Yan,Kang, Yifan,Wang, Bo,Ma, Yangmin,Szostak, Michal
, p. 803 - 811 (2021/01/28)
A metal-free C-H [5 + 1] annulation reaction of 2-arylanilines with diazo compounds has been achieved, giving rise to two types of prevalent phenanthridines via highly selective C-C cleavage. Compared to the simple N-H insertion manipulation of diazo, this method elegantly accomplishes a tandem N-H insertion/SEAr/C-C cleavage/aromatization reaction, and the synthetic utility of this new transformation is exemplified by the succinct syntheses of trisphaeridine and bicolorine alkaloids. This journal is
One-pot Cascade Reaction for the Synthesis of Phenanthridines via Suzuki Coupling/C?H Oxidation/Aromatization
Chen, Rener,Ding, Yuxin,Ma, Yongmin,Zhang, Yi
, p. 5697 - 5707 (2020/12/01)
A one-pot cascade coupling/annulation reaction for the synthesis of phenanthridines has been developed from arylboronic acids and o-bromo arylamides with DMSO as a carbon source. The desired phenanthridines were obtained in moderate to good yields by using simple procedure. (Figure presented.).
Synthesis of phenanthridines through iodine-supported intramolecular C-H amination and oxidation under visible light
Chen, Xuenian,Ma, Yan-Na,Gao, Yan,Jing, Yi,Li, Lixin,Zhang, Jie
, p. 12187 - 12198 (2020/11/10)
Herein, we report a metal-free and step-economic synthesis of phenanthridines from 2-biarylmethanamines under mild conditions. The reaction involves iodine-supported intramolecular C-H amination and oxidation of 5,6-dihydrophenanthridine under air and benign visible light. The mechanism study reveals that visible light plays a key role in both these steps.
A ruthenium-catalyzed free amine directed (5+1) annulation of anilines with olefins: Diverse synthesis of phenanthridine derivatives
Chowdhury, Deepan,Dana, Suman,Mandal, Anup,Baidya, Mahiuddin
supporting information, p. 11908 - 11911 (2019/10/11)
A ruthenium(ii)-catalyzed cross-ring (5+1) annulation between 2-aminobiphenyls and activated olefins is disclosed for succinct synthesis of valuable phenanthridine scaffolds. The protocol avails a common organic functional group, free amine, as a directing group and represents a unique combination of C-H activation/annulation/C-C bond cleavage cascade that bodes well in the production of bioactive alkaloids including trisphaeridine and bicolorine.
Boroquinol Complexes with Fused Extended Aromatic Backbones: Synthesis and Optical Properties
Elbert, Sven M.,Wagner, Philippe,Kanagasundaram, Thines,Rominger, Frank,Mastalerz, Michael
, p. 935 - 945 (2017/02/05)
Boron-based dyes are attractive synthetic targets due to their large variability of absorption and emission wavelengths. Through Pictet–Spengler cyclizations, followed by oxidation, π-extended boroquinols have been synthesized. During optimization of the
A new synthetic approach to 6-unsubstituted phenanthridine and phenanthridine-like compounds under mild and metal-free conditions
Tummatorn, Jumreang,Krajangsri, Suppachai,Norseeda, Krissada,Thongsornkleeb, Charnsak,Ruchirawat, Somsak
, p. 5077 - 5081 (2014/07/08)
A new and mild synthetic approach for the synthesis of 6-unsubstituted phenanthridine and phenanthridine-like compounds under metal-free conditions at room temperature has been developed. The strategy involved a tandem azide rearrangement/intramolecular annulation and oxidation reactions of biarylmethyl azide precursors to obtain the desired products in up to 99% yields with high regioselectivity.
LEWIS ACID PROMOTED PHOTOCYCLIZATION OF ARYLIMINES. STUDIES DIRECTED TOWARDS THE SYNTHESIS OF PENTACYCLIC NATURAL PRODUCTS.
Thompson, Charles M.,Docter, Stephen
, p. 5213 - 5216 (2007/10/02)
Arylimines are converted into 9-azaphenanthrene derivatives (38-46percent) when photolyzed in the presence of boron trifluoride etherate.
