Easy construction of furo[2,3-f]isoindole core by the IMDAV reaction between 3-(furyl)allylamines and α,β-unsaturated acid anhydrides

Add time:07/25/2019    Source:sciencedirect.com

The vinylogues of furfurylamines, easily available in two steps from furylacroleins (3-(furyl)allylamines), were studied in a tandem N-acylation/intramolecular [4+2] cycloaddition with maleic, pyrocinchonic, and citraconic anhydrides, as well as furylacryloyl and cinnamoyl chlorides. By using a domino reaction of 3-(furyl)allylamines and α,β-unsaturated acid anhydrides under mild conditions, various hexahydro-4H-furo[2,3-f]isoindoles and their carboxyl derivatives were synthesized efficiently. The domino sequence includes three steps: acylation of the nitrogen atom in 3-(furyl)allylamines, intramolecular Diels–Alder cycloaddition in the resulting N-acyl vinylfurans (IMDAV reaction), and prototropic shift of the adducts followed by recovery of aromaticity of the furan nucleus. The key step, IMDAV reaction, leads to the target products, furo[2,3-f]isoindoles, diastereoselectively and with relatively high yields.

We also recommend Trading Suppliers and Manufacturers of 2H-Isoindole-1-carboxylic acid (cas 109839-13-6). Pls Click Website Link as below: cas 109839-13-6 suppliers

Prev:Interactions of zinc octacarboxyphthalocyanine with selected amino acids and with albumin
Next:Traceless chirality transfer from a norbornene β-amino acid to pyrimido[2,1-a]isoindole enantiomers)