The Pomeranz–Fritsch reaction, also named Pomeranz–Fritsch cyclization, is a named reaction in organic chemistry. It is named after Paul Fritsch (1859–1913) and Cäsar Pomeranz (1860–1926).[1][2] In general it is a synthesis of isoquinoline.[2][3][4]
First the benzalaminoacetal 1 is built by the condensation of benzaldehyde and a 2,2-dialkoxyethylamine. After the condensation a hydrogen-atom is added to one of the alkoxy groups. Subsequently, an alcohol is removed. Next, the compound 2 is built. After that a second hydrogen-atom is added to the compound. In the last step a second alcohol is removed and the bicyclic system becomes aromatic.
The Pomeranz–Fritsch reaction has general application in the preparation of isoquinoline derivatives.
Isoquinolines find many applications, including:[3][4]
^ abPomeranz, C. (December 1893). "Uber eine neue Isochinolinsynthese". Monatshefte für Chemie. 14 (1): 116–119. doi:10.1007/BF01517862. S2CID95923801.
^ abWang, Zerong (2009). Comprehensive organic name reactions and reagents. Hoboken, N.J.: John Wiley. pp. 2256–2259. ISBN978-0-471-70450-8.
^ abcdKürti, László; Czakó, Barbara (2007). Strategic applications of named reactions in organic synthesis : background and detailed mechanisms ; 250 named reactions (Pbk. ed., [Nachdr.]. ed.). Amsterdam [u.a.]: Elsevier Academic Press. pp. 358–359. ISBN978-0-12-429785-2.
^ abLi, Jie Jack (2006). Name reactions : a collection of detailed reaction mechanisms ; [more than 300 reactions] (3., expanded ed.). Berlin [u.a.]: Springer. pp. 472–474. ISBN978-3-540-30030-4.