Nice prep and photo! I recall some interest in ring substituted phenylmaleimides or succinamides being researched at Oxford University as (I may be
wrong here) enzyme inhibitors/drugs but can not remember what the targets were
perhaps a lit search will yield some clues as to what I'm thinking about.Klute - 18-1-2009 at 12:15
Very nice! I like the pdf presentation! This could actually go into prepublication...
I would love to hear of the use of this product as a dienophile.
Nothing much to add! Good work!
Love to see more documents/work like this!Nicodem - 19-1-2009 at 01:19
Nice report.
I would however suggest to also try a direct one-step preparation which is also possible by simply refluxing maleic anhydride, aniline, TsOH (or other
suitable acid catalyst) in toluene or xylene in the presence of a polymerisation inhibitor such as hydroquinone or similar (most members here have
troubles obtaining acetanhydride). One such example is described in patent EP726252 (there are many other examples in the patent literature, but this
is I believe the simplest).
Panziandi, I doubt any N-phenylmaleimides could be seriously considered as (reversible) enzyme inhibitors or potential drugs. They have one of those
type of chemical functionalities that are consider a NO in medicinal chemistry - the maleimide group is a strongly electrophilic, it is Michael
alkylator, a dienophile and an enophile...panziandi - 19-1-2009 at 02:20
No no, this was about 6 years ago when I was in the pharmacology department someone over in chemistry was making these derivatives (I thought it was
to do with trying to inhibit some enzyme perhaps it wasn't but the work was related to something inthe pharmacology department!), perhaps purely for
research but it definitely was based on either the succinimides or maleimides (most likely the succinimide). I remember that they used the two step
process whereby they brought about the cyclic imide by refluxing with acetic anhydride as described by Ozone. I will try and do a literature search
because they must have published something!
N-Phenylmaleimide Anthracene Adduct PDF
Ozonelabs - 24-1-2009 at 12:36
Diels-Alder with N-Phenylmaleimide and Anthracene.
As requested in our last thread.
Attachment: NPMAAdduct.pdf (286kB) This file has been downloaded 729 times
Klute - 25-1-2009 at 04:03
Beautifull! Thank you very much!
So what's next on your list? Any uses of the formed product?Ozonelabs - 25-1-2009 at 04:32
Klute- we have been thinking very hard about what to do next and have been drawing blanks...
We were considering a Luminol synthesis (out of academic interest and becuase we were asked for one via e-mail), perhaps showing a Vilsmeier Haack
formylation, reductions etc.
This is why we ask for peoples requests! Otherwise we are unsure as to what people would like to see...Formula409 - 25-1-2009 at 04:42
Quote:
Originally posted by Ozonelabs
This is why we ask for peoples requests! Otherwise we are unsure as to what people would like to see...
Luminol sounds interesting. What route would you be taking? Keep up the great work.
Formula409.Ozonelabs - 25-1-2009 at 05:05
Formula409-
Phthalic Anhydride to 3/4 Nitrophthallic Anhydride with Fuming HNO3 and conc HNO3/ H2SO4.
3-Nitrophthalic Anhydride to 5-nitro-2,3-dihydro-1,4-phthalazinedione via sodium salt of the former and either Hydrazinium
Sulphate or Hydrazine Hydrate.
5-nitro-2,3-dihydro-1,4-phthalazinedione to luminol via sodium hydrosulfite.bfesser - 11-6-2009 at 09:31
Ozonelabs, did you take the melting range of your anthracene adduct? Thanks.Paddywhacker - 11-6-2009 at 18:51
You've drawn fumaranilic acid as the intermediate.Drunkguy - 1-7-2009 at 09:58
Anybody got any idea what the motivations might be for making this product?
It's elegant chemistry, although what function (if any) does N-Phenylmaleimide actually serve?
perhaps a lit search will yield some clues as to what I'm thinking about.