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DBL%20Hendrix%20small.png College chemistry, 1983

Derek Lowe The 2002 Model

Dbl%20new%20portrait%20B%26W.png After 10 years of blogging. . .

Derek Lowe, an Arkansan by birth, got his BA from Hendrix College and his PhD in organic chemistry from Duke before spending time in Germany on a Humboldt Fellowship on his post-doc. He's worked for several major pharmaceutical companies since 1989 on drug discovery projects against schizophrenia, Alzheimer's, diabetes, osteoporosis and other diseases. To contact Derek email him directly: derekb.lowe@gmail.com Twitter: Dereklowe

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« Great Moments in Heterocyclic Chemistry | Main | A Word to the Wise »

May 24, 2010

What's the Condensation Record?

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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) + TrackBacks (0) | Category: Chemical News


COMMENTS

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 Comment

2. 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 Comment

3. 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 Comment

4. 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 Comment

5. Anonymous on May 25, 2010 7:39 AM writes...

What's the yield of either the 5- or 4-components reaction?

Permalink to Comment

6. 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
Volume 47, Issue 7, 13 February 2006, Pages 1205-1207

Permalink to Comment

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 Comment

8. 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
Volume 47, Issue 7, 13 February 2006, Pages 1205-1207

Permalink to Comment

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 Comment

10. 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 Comment

11. 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 Comment

12. joeylawn on May 25, 2010 8:00 PM writes...

Nothing, I repeat, Nothing good can possibly come out of Iran!

Permalink to Comment

13. OTK on May 26, 2010 5:02 AM writes...

Ugi and Doemling published a 7 component reaction some time ago
DOI: 10.1002/anie.199305631

Permalink to Comment

14. Sili on May 26, 2010 10:33 AM writes...

Nothing, I repeat, Nothing good can possibly come out of Iran!
Have you met mrs Lowe? Permalink to Comment

15. okemist on May 26, 2010 10:59 AM writes...

Have you met mrs Lowe?

The better half of in the pipline!

Permalink to Comment

16. 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 Comment

17. 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 Comment

18. Mr. Fiddy on May 31, 2010 8:53 PM writes...

How about the primodial ooze that became us and
Arkansas Chocolate Pecan Pie?

Permalink to Comment

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