233-04-5Relevant articles and documents
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
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
Cascade C-C and C-N Bond Formation: A Straightforward Synthesis of Phenanthridines and Fused Quinolines
Borah, Ashwini,Gogoi, Pranjal
supporting information, p. 2200 - 2206 (2016/05/09)
A Pd-catalyzed cascade process has been developed for the synthesis of quinoline and phenanthridine derivatives from various β-chloro α,β-unsaturated aldehydes and 2-chloroaryl aldehydes, respectively, in good to high yields. The reaction proceeds through Pd-catalyzed cascade carbon-carbon and carbon-nitrogen bond formation in a single reaction vessel. The requisite β-chloro α,β-unsaturated aldehydes were efficiently synthesized from their corresponding carbonyl compounds. The use of the ligand Sphos with Pd(OAc)2 is crucial for the successful implementation of the present cascade process. This synthetic protocol is also applied for the gram-scale synthesis of a trispheridine alkaloid.
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.
The First Synthesis of Thienoisoquinolines and an Improved Synthesis of Phenanthridine and Thienoquinolines through Pd(0) Catalyzed Coupling of ortho-Formylarylboronic Acids with Functionalized Aryl Halides
Yang, Youhua,Hoernfeldt, Anna-Britta,Gronowitz, Salo
, p. 865 - 868 (2007/10/02)
All three isomeric hitherto unknown thienoisoquinolines have been synthesized in high yields by the Pd(0)-catalyzed coupling of 2-formylbenzeneboronic acid with t-butyl-N-(ortho-halothienyl)carbamates.When 2-bromoacetanilide, instead of 2-bromoaniline, was coupled with ortho-formylarylboronic acids under Pd-catalysis, phenanthridine and thienoquinolines were obtained in improved yields. Total assignments of 1H nmr spectra of thienoisoquinolines and thienoquinolines are reported.Assignments are based on high resolution 300 MHz 1H nmr spectra, two-dimentional 1H-13C chemical shift correlation spectra and one-dimentional INADEQUATE 13C nmr spectroscopy.
