51116-29-1Relevant academic research and scientific papers
Rapid and convergent assembly of natural benzo[c]phenanthridines by palladium/norbornene catalysis
Deyris, Pierre-Alexandre,Caneque-Cobo, Tatiana,Gomes, Filipe,Narbonne, Vanessa,Maestri, Giovanni,Malacria, Max
, p. 807 - 815 (2016/09/09)
A straightforward total synthesis of a small panel of natural benzo[c]phenanthridines is described. The selective coupling of an aryl triflate with a bromobenzylamine by means of palladium/norbornene joint catalysis and a sequential transfer hydrogenation
A versatile synthesis of fully aromatic benzo[c]phenanthridine alkaloids
Geen, Graham R.,Mann, Inderjit S.,Mullane, M. Valerie,McKillop, Alexander
, p. 9875 - 9894 (2007/10/03)
A versatile new approach for the synthesis of benzo[c]phenanthridine alkaloids is described and is illustrated by the preparation of eight different alkaloids. The key steps are Smiles rearrangements, which allow easy access to 2-bromo-1-naphthylamines from 2-bromo-1-naphthols, and the attachment of the D-ring unit by Suzuki coupling.
A versatile synthesis of benzo[c]phenanthridine alkaloids
Geen, Graham R.,Mann, Inderjit S.,Mullane, M. Valerie,McKillop, Alexander
, p. 1647 - 1648 (2007/10/03)
Suzuki coupling between 2-bromo-1-formamidonaphthalenes and arylboronic acids is the key step in a versatile synthesis of benzo[c]phenanthridine alkaloids, illustrated by the synthesis of norallonitidine, nornitidine, noravicine, allonitidine, nitidine and avicine.
Direct Synthesis of Benzophenanthridines and Benzophenanthridones via SRN1 Reactions
Beugelmans, Rene,Chastanet, Jacqueline,Ginsburg, Helene,Quintero-Cortes, Leticia,Roussi, Georges
, p. 4933 - 4938 (2007/10/02)
A straightforward and high-yield route to the 11,12-dihydrobenzophenanthridine (3) and 11,12-dihydrobenzophenanthridone (14) ring systems is based upon an SRN1 reaction between 2-halobenzylamines 1 or 2-halobenzoic acids 11 and enolates derived from tetralones 2.The efficient dehydrogenation of 3 or 14 gives the benzophenthridines 4 or benzophenanthridones 15.Use of properly substituted reactants leads to nitidine, avicine, and fagaronine and to analogues of those natural products.
