Pomeranz–Fritsch reaction
| Pomeranz–Fritsch reaction | |
|---|---|
| Named after | Cäsar Pomeranz Paul Fritsch |
| Reaction type | Ring forming reaction |
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]
General reaction scheme
The reaction below shows the acid-promoted synthesis of isoquinoline from benzaldehyde and a 2,2-dialkoxyethylamine.[5]
Various
methyl and ethyl
groups, can be used as substituent R.
In the archetypical reaction
Later, a wide range of diverse isoquinolines were successfully prepared.[4]Reaction mechanism
A possible mechanism is depicted below:[5]
First the benzalaminoacetal 1 is built by the
aromatic
.
Applications
The Pomeranz–Fritsch reaction has general application in the preparation of isoquinoline derivatives.
Isoquinolines find many applications, including:[3][4]
- topical anesthetics such as dimethisoquin:
- vasodilators, a well-known example, papaverine, shown below.
See also
References
- ^ S2CID 95923801.
- ^ .
- ^ ISBN 978-0-471-70450-8.
- ^ ISBN 978-0-12-429785-2.
- ^ ISBN 978-3-540-30030-4.