221454-80-4

Upstream product

• 100-01-6 4-nitro-aniline 
• 221454-64-4 3-methoxyestra-16,17-seco-1,3,5⁽¹⁰⁾-trien-17-al 
• 118335-53-8 3-methoxy-14β-(prop-2-en-yl)-des-D-estra-1,3,5(10)-trien-13α-carbaldehyde 

Relevant academic research and scientific papers

Synthesis of Novel D-Secoestrone Isoquinuclidines by an Unpredicted Iminium Ion-Induced 1,5-Hydride Shift

Unique 9,13-bridged D-secoestrone alkaloids have been synthesized and structurally characterized. Treatment of 3-methoxy-16,17-secoestra-1,3,5(10)trien-17-al (6a) with aniline (7) or substituted aniline derivates 8-28 in the presence of different Lewis and Broensted acids produces the bridged azaestrone derivatives 51-67 and the alkenes 68-73 in high yields in a domino-type process. The imines 29-50 are proposed as intermediates, undergoing 1,5-hydride shifts via the iminium ion salts 75 to give the cations 77, which, depending on the substitution pattern on the aniline moiety, either afford the bridged compounds through a nucleophilic addition of the formed secondary amine to the benzylic carbocation or give the alkenes through the abstraction of a proton at C-8.