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May 24, 2010
What's the Condensation Record?
Posted by Derek
There are probably some other reactions of the same order as this one - but does anyone know a higher one? I'm talking about this four-component condensation reaction, reported from a lab in Iran, which actually makes semi-useful looking oxadiazoles. Anyone know of a five-component condensation? A real one, I mean, that makes a real product, as opposed to dark gooey stuff. Those, I can imagine.
Comments (18)
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1. Handles on May 24, 2010 11:56 PM writes...
Heres a lecture from Ivar Ugi himself:
http://www.mdpi.com/1420-3049/8/1/53/
Scheme 7 shows a seven-component condensation featuring good ole t-Bu isonitrile.
Permalink to Comment2. Anonymous on May 25, 2010 12:51 AM writes...
Multicomponent reactions are really useful and powerful ways to create fairly complex molecules from simple starting materials. For example, check this review out: http://dx.doi.org/10.1016/j.cbpa.2010.03.003
Neat stuff.
Permalink to Comment3. partial agonist on May 25, 2010 7:24 AM writes...
5-component variant of the Ugi reaction from Robert Armstrong:
J. Org. Chem. 1998, 63, 867-871
Permalink to Comment4. josh on May 25, 2010 7:34 AM writes...
Im not sure any 5 exist but as you stated, 4 is not uncommon, the Ugi reaction has be around for some 48 years
Permalink to Comment5. Anonymous on May 25, 2010 7:39 AM writes...
What's the yield of either the 5- or 4-components reaction?
Permalink to Comment6. JwNl on May 25, 2010 7:39 AM writes...
A new approach to four- and five-component Ugi condensations starting from nitriles
http://dx.doi.org/10.1016/j.tetlet.2005.12.011
Tetrahedron Letters
Permalink to CommentVolume 47, Issue 7, 13 February 2006, Pages 1205-1207
7. partial agonist on May 25, 2010 7:44 AM writes...
6-component Petasis-Ugi reaction:
Tetrahedron Letters, Volume 44, Issue 3, 13 January 2003, Pages 603-605
It is actually 2 steps/1 pot though, since you concentrate the solution after the Petasis step, then add the other 3 components
Permalink to Comment8. JwNl on May 25, 2010 7:47 AM writes...
A new approach to four- and five-component Ugi condensations starting from nitriles
http://dx.doi.org/10.1016/j.tetlet.2005.12.011
Tetrahedron Letters
Permalink to CommentVolume 47, Issue 7, 13 February 2006, Pages 1205-1207
9. Al Osteric on May 25, 2010 7:50 AM writes...
For what it's worth, there's an 8-component reaction that was published in 2009:
http://www3.interscience.wiley.com/journal/122490539/abstract
Permalink to Comment10. boron bodger on May 25, 2010 8:13 AM writes...
8-component reaction. Not sure what else to say about it though.
http://www3.interscience.wiley.com/journal/122490539/abstract
Permalink to Comment11. John Spevacek on May 25, 2010 8:39 AM writes...
I imagine proposing any condensation polymer (PET, nylon 6,6 or 6, 10 or x,y) is beyond the spirit of the question? Certainly there are hundreds of monomers in some of the resulting molecules.
At the same time, one certainly could dump 8 or more different monomers in a pot and run a polymerization reaction. The result would more like a statistical copolymer than anything else and they are traditionally run be radical additions.
Permalink to Comment12. joeylawn on May 25, 2010 8:00 PM writes...
Nothing, I repeat, Nothing good can possibly come out of Iran!
Permalink to Comment13. OTK on May 26, 2010 5:02 AM writes...
Ugi and Doemling published a 7 component reaction some time ago
Permalink to CommentDOI: 10.1002/anie.199305631
14. Sili on May 26, 2010 10:33 AM writes...
Have you met mrs Lowe? Permalink to Comment15. okemist on May 26, 2010 10:59 AM writes...
Have you met mrs Lowe?
The better half of in the pipline!
Permalink to Comment16. dddddd on May 28, 2010 2:55 AM writes...
Interestingly, if you Google "Condensation Record" this site is the top hit.
OK, that wasn't interesting. Back to work then.
Permalink to Comment17. Jonadab the Unsightly One on May 31, 2010 7:09 AM writes...
I've got a twenty-seven component condensation that gives a 94% yield, but this margin is too narrow to contain it.
Permalink to Comment18. Mr. Fiddy on May 31, 2010 8:53 PM writes...
How about the primodial ooze that became us and
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