93772-12-4Relevant academic research and scientific papers
A NEW PRECURSOR TO 3,4-DIDEHYDROPYRIDINE, AND ITS USE IN THE SYNTHESIS OF THE ANTITUMOR ALKALOID ELLIPTICINE
May, Christopher,Moody, Christopher J.
, p. 247 - 250 (2007/10/02)
A concise synthesis of the antitumor alkaloid ellipticine (1) is reported.The route involves a Diels-Alder reaction between 1,4-dimethylpyranoindol-3-one (3), easily prepared in two steps from indole, and 3,4-didehydropyridine (4), and for its successful execution required the development of a new thermal, reagent-free precursor to the aryne.This precursor, 3-(3,3-dimethyltriazen-1-yl)pyridine-4-carboxylic acid (10a), prepared from 3-aminopyridine-4-carboxylic acid, decomposes in boiling acetonitrile to generate 3,4-didehydropyridine which can be intercepted in Diels-Alder reactions with tetraphenylcyclopentadienone, furan, and 2,5-dimethylfuran.The triazenes (10b) and (10c) can be prepared and decomposed similarly.The key Diels-Alder reaction between the pyranoindolone (3) and 3,4-didehydropyridine (4) gives ellipticine (1) in 20 percent yield, together with an equal amount of isoellipticine (14).
A CONVENIENT PRECURSOR TO 3,4-DIDEHYDROPYRIDINE
May, Christopher,Moody, Christopher J.
, p. 2123 - 2124 (2007/10/02)
The preparation of 3-(3,3-dimethyltriazen-1-yl)pyridine-4-carboxylic acid (5), a convenient shelf-stable precursor to 3,4-didehydropyridine, is described.
A Concise Synthesis of the Antitumour Alkaloid Ellipticine
May, Christopher,Moody, Christopher J.
, p. 926 - 927 (2007/10/02)
A short synthesis of the antitumour alkaloid ellipticine, based on the Diels-Alder reaction between 1,4-dimethylpyranoindol-3-one (2) and 3,4-didehydropyridine, is described.
