Organic Chemistry

Development of new syntheses in organic chemistry

Exploring useful and convenient reactions of heteroaromatic compounds

As numerous natural products and medicinal drugs are made up of nitrogen-containing heteroaromatics, studies of these compounds are of considerable interest to many chemists. Our research group has begun exploring various useful and convenient reactions of heteroaromatic compounds.


1. Application of the Mitsunobu reagent to the cyclization of a nitrogen-containing heteroaromatic ring
We have found that a mixture of benzoic acid, triphenylphosphine, and diethyl azodicarboxylate was heated to afford 1,3,4-oxadiazole derivatives in good yield. Further studies will investigate whether all carboxylic acids can be used in this cyclization.
2. Preparation and reaction of heteroarylphosphonium salts with base and carbonyl compounds
Elimination of the heteroaryl group was achieved by treating the heteroaryltriphenylphosphonium iodides with a base. Further, the heteroaryl group was trapped with pivalaldehyde to introduce a pivaloyl substituent onto the heteroaromatic ring.

Professor

Masahito EgiPhD
egi@u-shizuoka-ken.ac.jp
TEL.+81-54-264-5542

Professor

Details are here

 

Figure.1

Elimination of the heteroaryl group was achieved by treating the heteroaryltriphenylphosphonium iodides with a base. Further, the heteroaryl group was trapped with pivalaldehyde to introduce a pivaloyl substituent onto the heteroaromatic ring.

Figure.2

Preparation of 1,3,4-oxadiazole derivatives by reaction of benzoic acid with PPh3 and DEAD

References

  1. Heterocycles, 80, 601–606 (2010)
  2. Tetrahedron Lett., 49, 1492–1494 (2008)
  3. Lett. Org. Chem., 3, 626–628 (2006)
  4. J. Org. Chem., 68, 2054–2057 (2003)