32821-75-3Relevant articles and documents
Keiko et al.
, (1973)
Towards the synthesis of osteoclast inhibitor SB-242784
Conde, Jose J.,McGuire, Michael,Wallace, Michael
, p. 3081 - 3084 (2007/10/03)
Osteoclast inhibitor SB-242784 (1) was prepared from pivotal indol intermediate 4. A 'Stille' cross coupling of organotin 2c with bromo acrylate 11 afforded diene 12 which was also obtained via a reduction-isomerization process of enyne 16. Bromoamide 3 was prepared from the corresponding acid 7 which was readily obtained from bromopyruvic acid.
Experiments Towards the Synthesis of the Ergot Alkaloids and Related Structures. Part 4. Lysergic Acid-An Attempted 'Endo-amide' Approach
Bowman, Ralph E.
, p. 1897 - 1904 (2007/10/02)
Two attempts to synthesise the tricyclic α-keto-amide (6) are described.In the first, 1,2,3,4-tetradihydro-2-methylaminonaphthalen-1-one (3) was allowed to react with pyridine-hydroxymaleic anhydride at -20 deg C and then at room temperature to give a complex mixture from which the naphth-1,4-oxazinone (14), 2-pyruvamido-1-tetralone (16; R=Ac) contaminated with the oxazinone (14) and the phenolic acid (13c) were isolated.A tetracyclic oxazinone was also obtained from the appropriate methylaminotetrahydroacenaphthenone but not from the corresponiding benzindolone (7; R=NHMe.HCl).In the second, the N-methyldione (10) was converted in three stages into the tricyclic acid (13c) which proved unexpectedly stable.However, its triethylamine salt lost carbon dioxide at 140 deg C to give not the required keto-amide (6) but the isomeric hydroxybenzquinolone (13d).Both the oxazinone (14) and the impure pyruvamido-ketone (16; R=Ac) were converted within seconds by treatment with 2 M-sodium hydroxide into the sparingly soluble sodium salt of the phenol (13d) as was the pure pyruvamido ketone whose synthesis is described.
