383191-51-3Relevant articles and documents
Sequential Addition of Amines to Nitrile and Carbon-Carbon Multiple Bond: A Route to 7-Amino-5 H-dibenzo[ c,e]azepines
Hu, Kun,Liu, Ruiting,Zhou, Xigeng
supporting information, p. 6946 - 6950 (2021/09/11)
A rare earth metal-catalyzed sequential inter- and intramolecular C-N bond formation of 2-nitrile-2′-alkenyl(alkynyl)biphenyls with amines has been developed, which provides a straightforward and efficient access to a range of new functional dibenzo[c,e]azepines. This represents the first examples of direct construction of seven-membered azaheterocycle from unsaturated nitriles and amines. Such transformations have the advantages of avoiding the use of additives, easily available starting materials, step- and high atom-economy, mild reaction conditions, and high selectivity.
Domino Palladium-Catalyzed Double Norbornene Insertion/Annulation Reaction: Expeditious Synthesis of Overcrowded Tetrasubstituted Olefins
Naveen, Kanagaraj,Perumal, Paramasivan Thirumalai,Cho, Deug-Hee
supporting information, p. 4350 - 4354 (2019/06/14)
A Pd-catalyzed domino process involving a double norbornene insertion/annulation reaction was developed for the expeditious synthesis of overcrowded olefins. In this one-pot reaction, four new C-C bond formations were achieved by three consecutive Heck ca
Novel synthesis of 4,5-diarylphenanthrenes via C2-C6 cyclization of benzannulated enyne-allenes
Li,Petersen,Wang
, p. 7804 - 7810 (2007/10/03)
A new synthetic pathway to the 4,5-diarylphenanthrenes 8 having a helical twist in their structures was developed. The synthetic sequence involves condensation of the diketone 5 with 2 equiv of the lithium acetylides derived from the diacetylenes 4 followed by protonation to produce the propargylic alcohols 6. Reduction of 6 with triethylsilane in the presence of trifluoroacetic acid furnished the tetraacetylenic hydrocarbons 7 in nearly quantitative yields. Treatment of 7 with potassium tertbutoxide under refluxing toluene at 110 °C for up to 10 h then furnished the 4,5-diarylphenanthrenes 8. Apparently, the transformation from 7 to 8 involves initial prototropic isomerizations to form the benzannulated enyne-allenes 9. Two subsequent formal intramolecular Diels-Alder reactions via the biradicals 10 and 12 derived from the C2-C6 cyclizations then led to 13, which in turn underwent tautomerizations to give 8. The structure of 8a was established by the X-ray structure analysis, showing that the two phenyl substituents are bent away from each other and the central aromatic system is severely distorted with a helical twist. The existence of a helical twist in 8 imposed by the aryl groups at the 4- and 5-positions was also revealed with a set of AB 1H NMR signals for the diastereotopic methylene hydrogens on the five-membered rings.